MUSIC OPRAH WINFREY: Today, 30, 40, 50, 60. How you can look great at any age. Fantastic. All I got to say is go 50, go 50. LINDA, 51: I'm blown away. I just feel beautiful. WINFREY: Transformations that could take years off your looks, next. [APPLAUSE] WINFREY: On Monday, we wrapped up our two-part series on aging well, telling you all the right things to eat and do to live longer, healthier, younger with Dr. Oz. Today, we're taking on your closet because you can eat well, you can have all the vegetables and Omega-3s and still look bad. [LAUGHTER] WINFREY: So to help you look your best at any age, we have the experts here. You're gonna get invaluable advice from style experts on how to now dress from your 30s to your 60s. This is going to be--so everybody who's 70, don't say I left you out. [LAUGHTER] WINFREY: If you're 70, you can wear what the 60-year-olds are wearing, okay? [LAUGHTER] CHARLA KRUPP: Yeah. WINFREY: So let's meet the people who are here to help. Stacy London is the host of TLC's "Fashionably Late" and "What Not to Wear." [CHEERS AND APPLAUSE] WINFREY: Lloyd Boston, author of "Before You Put That On." [LAUGHTER] [CHEERS AND APPLAUSE] WINFREY: And Charla Krupp, author of "How Not to Look Old." [CHEERS AND APPLAUSE] WINFREY: Just "How Not to Look Old," which is coming out in January. Welcome to all of you here. LLOYD BOSTON: Great to be here. STACY LONDON: Great to be here. WINFREY: So, what is the number one mistake that people make, Lloyd? Mr. BOSTON: Well, for me, I think it's women who shop by the size number and not the fit. WINFREY: Right. Mr. BOSTON: They're married to an eight but the 10 starts fitting a little better. WINFREY: They're laughing. [LAUGHTER] Mr. BOSTON: Make that 10. WINFREY: They're laughing, says we've all done it. Mr. BOSTON: Just go ahead and get the 10 and cut the number out. BOSTON: And your clothes will look so much sexier, I promise you. WINFREY: Yeah. WINFREY: That is true. Ms. LONDON: It is. WINFREY: That is true. But it's hard to move to double digits, you know? [LAUGHTER] WINFREY: It is. I've been back and forth, I know. It's hard to move to the double digits. Mr. BOSTON: It's all up here. WINFREY: It's all up here. Mr. BOSTON: It's not labeled on the outside. WINFREY: Okay. Mr. BOSTON: It's all up here. WINFREY: And you're better off just going to the next size 'cause you're gonna look thinner rather than stuffing yourself in a smaller size. Mr. BOSTON: And having that biscuit can moment or having something... [LAUGHTER] Mr. BOSTON: You know the biscuit can. It cracks and then it pops. WINFREY: Yeah, yeah, yeah. Mr. BOSTON: Yeah. Not good. WINFREY: Or your arms are so tight in the jacket... Ms. LONDON: Oh. [LAUGHTER] WINFREY: ...that you're like, don't shake my hand. [LAUGHTER] WINFREY: All right, number one mistake. Ms. LONDON: I would say, it's that women are too concerned with being trendy and that they're not looking at trends through the right filter. And there are three things always that you should consider, your body type, your age, and your lifestyle. And that's how you decide what trends are gonna work for you. If you're standing at a buffet table, you don't take everything, right? You take the things that you like, the little bits and pieces. That's the way you need to look at trends. Not every trend works for every person. And your filter is your way of choosing what's gonna work for you. WINFREY: Okay, I love that. Ms. KRUPP: That's good. WINFREY: That's really good, both you. All right, top that. [LAUGHTER] Ms. KRUPP: I will. WINFREY: Okay. Ms. KRUPP: I think women in America are so hung up on comfort, they walk around in clothes like they're going to the gym. [APPLAUSE] WINFREY: That is true. That is true. I have to say I'm guilty of that. I am guilty of that. It's my number one--that's how I love to dress. Ms. KRUPP: But sneakers on the street, I'm sorry... WINFREY: Yeah, that, I don't do. Ms. KRUPP: ...they are for running only. And when you go to a foreign country and you're dressed in your track suit, they're not gonna treat you with the respect you want. WINFREY: Yeah. Ms. KRUPP: If you dress well, you will get people to sit up and... WINFREY: Well, not even for a foreign country, here. Ms. KRUPP: Yes. WINFREY: Go into some of the better dress stores in your track suit. Ms. KRUPP: Right. WINFREY: Yeah. Listen, I've had to go home and change clothes, 'cause I thought, well, I need more respect. I'm gonna go put on something... [LAUGHTER] Ms. KRUPP: Good idea. WINFREY: No, I'm not kidding. That happened to me at a store here, which I won't mention the name until we go to commercial break, but let's... Mr. BOSTON: All right. [LAUGHTER] WINFREY: Let's start with dressing in your 30s. For many women, the transition to dressing like a grown up really doesn't come easy. So meet Cathy. CATHY, 35: I'm 35 years old and I wear a lot of my daughter's clothes. MADALYN, 12: Welcome to my closet. These are some of my mom's favorite clothes to wear. She's got my miniskirt. She's got my crop jacket. CATHY: These flying capris I like. I like wild and crazy things that you find in the junior's department. MADALYN: She goes to the store and then, people stare at her. CATHY: A lot of the things I like to wear are tank tops. I like to wear jeans skirts. This is actually my daughter's. I don't wanna wear old lady, frumpy clothes but I'm afraid that sometimes, I don't always look age appropriate. MADALYN: Sometimes, it can be embarrassing when my friends go, oh, my gosh, what is your mom wearing? She needs to look a little bit more her age. WINFREY: So Stacy put together a new age appropriate look for 35-year-old Cathy. Okay, come on out. Let's see what that is, Cathy. Oh. [CHEERS AND APPLAUSE] Ms. LONDON: Now we are talking hot. Mr. BOSTON: Yeah. Ms. LONDON: Cathy is a 35-year-old, stay-at-home mom. WINFREY: Yes. Ms. LONDON: But she was dressing like her 12-year-old daughter. WINFREY: Yes. Ms. LONDON: And we wanted something that was still gonna be casual but cool. WINFREY: Yes. Ms. LONDON: And this trend is patent leather. WINFREY: Yes. Ms. LONDON: Now in your 30s, you can still pull off patent leather in a bigger piece. Do something with the traditional shape like this Doma jacket because that will give you longevity. It's an investment piece. You'll be able to wear it for a long time. You wanna do a piece that's cut close to the body if you're a petite, great little Moschino knit underneath. We did the Ava straight legged Citizens of Humanity jean here, with a comfy Cole Haan boot. And I did have to give her a heel 'cause she's so tiny. WINFREY: Yeah. Ms. LONDON: And I didn't want her in a high heel sneaker. WINFREY: Is that one of those Cole Haan boots that come with... Ms. LONDON: With the Nike air technology. WINFREY: Yeah, that I love. Yoo-ha. Ms. LONDON: So we're doing a little bit cool, a little bit rocker, she's still hip because she's in her 30s. But when you get older, like your 40s and 50s, you wanna start to look at this trend in a smaller amount. WINFREY: Okay, so let's see what you did. Ms. LONDON: So here we're doing for the 40s, a signature patent flat boot. WINFREY: I love that. Ms. LONDON: Okay, this is Stuart Weitzman, we're doing it with a great cashmere sweater dress, Dolce bag, no, it does not have to match the boot. That's a lot of patent on a little person... WINFREY: Yeah. Ms. LONDON: ...or even when you're taller, you just want one signature piece. And in your 50s, when you're really doing something like a signature print, look for more interesting patent, okay? Here we have an Yves Saint Laurent frame bag in green. WINFREY: Love it. Ms. LONDON: And we're doing a tortoise patent shoe from Stuart Weitzman, again the boot is from Stuart Weitzman, as well, and this look, again, just touches a patent is the way to do it. As you age, less is more. WINFREY: Right. Perfect. Perfection. Thank you so much, models. Thank you so much. [CHEERS AND APPLAUSE] WINFREY: Okay, next is a working mom of two who once competed for Mrs. Ohio. Two years later, she says she knows she's not dressing her best and she needs a little jumpstart. Mr. BOSTON: Just a little jumpstart. WINFREY: Yeah, a little jumpstart, okay? Take a look at her home video confession. CENELL, 36: I'm 36 and between work and my kids, I worry that I've let myself go. My staples are comfortable sweats and jeans. It was very easy for me just to throw on something like this and be comfortable. These are my favorite pants. I wear them, like, at least, maybe, three, probably about three times a week. My capris are really comfy and (makes noise) sexy. And this is what I look like when I dress up, wonderful. I've actually had this outfit for, since 1993. [LAUGHTER] CENELL: This dress I probably have had-- I picked it out, kind of makes me look a little older for me than it should. This one, my sister-in-law, Laurie, told me looks like a muumuu. She told me I need to get rid of it. I think it's pretty beautiful. WINFREY: Wow, so let's see Cenell's new look. Come on... Mr. BOSTON: Cenell looks so great. WINFREY: Okay. Mr. BOSTON: If you see her hit this runway, she is a hot body. Yeah. [CHEERS AND APPLAUSE] Mr. BOSTON: Yeah. That's my girl and I love that. Who knew? And the big trend, look at that, the big trend, here, Oprah, are metallics. Metallic bring out that inner shine. Notice how sizzling and sexy. WINFREY: Well... Mr. BOSTON: Again, the big trend is metallics. WINFREY: ...she loves herself so much, she can't even stop looking at herself. [LAUGHTER] Mr. BOSTON: Look at that smile. WINFREY: Wow. Mr. BOSTON: She is ready to shine and, again, the big trend is metallics. She's in her 30s, I wanted her look like she's in her 30s. She looks like she's in her 20s now. WINFREY: Yeah. Mr. BOSTON: And the good thing about this, this entire look is from Saks Fifth Avenue, this is a cheeky little party dress by Marc Jacobs. What I love about Cenell, she's a busy mom. A lot of gals out there are dressing just like her in sweats and jeans. She can put this on over her favorite pair of dark jeans and... BOSTON: ...do a girls' night out. WINFREY: Yeah. Mr. BOSTON: Or she could do sexy boots or heels and take it to a candlelight dinner with her man. You could also do it in different decades. Let me show you how to do it in your 40s... WINFREY: Yes. WINFREY: Yeah. Mr. BOSTON: ...as well as... LONDON: No. WINFREY: 'Cause you don't wanna have that on... WINFREY: ...if you're my age, right? [LAUGHTER] Mr. BOSTON: No, this is for the 30s gal. WINFREY: This is for the 30s. Okay, here are 40s? Mr. BOSTON: Take a look at our 40s gal, who actually looks very young to be 40 but she's pulling this 40 look off so beautifully. It's a sweater set. I could see you pulling this off in a heartbeat. BOSTON: Notice the shine comes down. WINFREY: Yes. Yes. WINFREY: I could wear some 40 things. [LAUGHTER] Mr. BOSTON: Just a little, yeah, you got it. WINFREY: Okay, good. Mr. BOSTON: The shine comes down, it's woven in, so it just... WINFREY: Yeah. Mr. BOSTON: Here or there and we cooled it down, Oprah, with cream pants and a cream bag. Ladies, wear your creams and whites straight through the fall and winter, those rules are gone. Do it this way. If you're in your 50s... WINFREY: Are they really gone? Ms. LONDON: Yes. Mr. BOSTON: They're gone. They never existed. It was an old thing about shoes in the south. WINFREY: No, they did exist. [LAUGHTER] Mr. BOSTON: Only shoes, though. WINFREY: Okay. Mr. BOSTON: But it was only--and then women took it like the telephone game, but you can do it. If the fabric is seasonally appropriate, wear that corduroy in cream, wear those denims in cream or white. You're the lady that lights up the room, like she is. BOSTON: 50s and 60s, do your best fabrics because if you're taking a chance on shine, make sure you're doing leather, gorgeous lace... WINFREY: Okay. WINFREY: Very nice. Mr. BOSTON: ...hot little evening bag, and make sure the fabric is so perfect. WINFREY: Love it. Mr. BOSTON: This is great. Ms. BOSTON: Thank you, shine. LONDON: Yeah. [APPLAUSE] WINFREY: Love it. WINFREY: Great, great, great, ladies. She's lighting up the room. Ms. LONDON: I know, she just is. I know. WINFREY: Oh. We'll be right back. We'll be right back. WINFREY: Coming up, she's only 44 but she's been offered a senior citizen's discount at her local store. Ouch. If you're dressing too old for your age, we're gonna help you, next. MUSIC MUSIC [CHEERS AND APPLAUSE] WINFREY: So, are your clothes aging you? We've been talking about keeping yourself more youthful. It's the hot topic this year, how to age brilliantly, from your physical health to your outer layers. Fashion experts Lloyd Boston, Stacy London and Charla Krupp are here to help you dress great at every age. So here's a challenge that millions of aging women face. Watch this one. KIMBERLY, 38: I'm 38, and I'm really frustrated with how my clothes fit me after having four children. Kind of depressing to look in here. I don't even know. I mean, look at this old jean skirt. Like, I think that it fit me a few years ago. It was supposed to be a hip thing, and now it's got to ride up high because my ever increasing midsection. When I wear fitted tops like this, or shirts, I just feel like it's hugging my fat. I don't know what to do about it. I don't really think I'm old enough for old lady's jeans, but I don't like my butt hanging out of junior jeans either. WINFREY: So Charla gave Kimberly a few tricks to help hide her back fat and slim her stomach. So take a look at Kimberly before. We all know what that's like. And you can see where her problem areas are. And she was so nice of us to let us bring our cameras in there. Ms. KRUPP: So nice. [LAUGHTER] KRUPP: She was such an incredible... WINFREY: Don't you think? Yes. Ms. KRUPP: ...sport, Oprah, I have to say. Just being seen on national television, we got to give her a hand when she comes out. WINFREY: So--well, we're gonna give her a hand. Let's see the difference. Ms. KRUPP: Yeah. [APPLAUSE] WINFREY: Come on out. [CHEERS AND APPLAUSE] WINFREY: Wowee. Wowee. Ms. KRUPP: All about the patent accessories. WINFREY: All about the patent accessories. Ms. KRUPP: The trend Kimberly is wearing is the wide leg pant. I have to tell you, if you're going, no way, that's not for me, try them on. They are the most comfortable pant. They have extra roomy space in the thigh area, where we all need it. And the trick with Kimberly, she has back fat, a lot of people... [LAUGHTER] Ms. KRUPP: You know, the older you get, the more our bodies go south. We've got to redirect it north. And the piece that we worked miracles was Lipo in a Box. Here is the piece. Ms. KRUPP: It's $40, it's high-waisted, and it goes down to a mid-thigh biker short. WINFREY: And who makes it? Ms. KRUPP: This is from Lipo in a Box. Now, would you rather get lipo or Lipo in a Box? [LAUGHTER] WINFREY: I love that. It's called Lipo in a Box? Ms. KRUPP: And you buy it at lipoinabox.com. It's $40. I'm wearing the same one today. Too much information, I am sure. [LAUGHTER] WINFREY: Let me see. Let me see. Mr. BOSTON: I have one on, too, actually. [LAUGHTER] Mr. BOSTON: They really work. Very smooth. [APPLAUSE] WINFREY: Wow. Lipo in a Box. What a great--how does it feel? KIMBERLY: It feels great. WINFREY: Really? KIMBERLY: Yes. Ms. KRUPP: The other trick for Kimberly is, she was wearing her pants too low. She needed a high-rise. WINFREY: Yeah. But see, everybody has been told that those were mom jeans when you do it that way. Ms. KRUPP: I know. But now, it's a high-rise could look good. If the pant slims you out, it makes her look long and lean... WINFREY: All right. Let's look at this in the 40's, in the 40's. And then, in the 40's, you could wear a low slung because you're still young. And we love this swingy jacket. And this outfit is from Saks. And then in the 60's, I love that this Oscar de la Renta blouse... WINFREY: Whoo. I love Oscar. Ms. KRUPP: ...is the answer to, I feel bad about my neck... WINFREY: Yes. Ms. KRUPP: ...wear this blouse. WINFREY: Yes. Wow. [APPLAUSE] Ms. KRUPP: It really brings attention to you face. And this is a Ralph Lauren... KRUPP: ...collection pants. But you wanna be elegant when you're in your 60's. And the older you are, the slimmer the wide leg pant. There's extreme wide legs... WINFREY: Isn't that beautiful? WINFREY: Yes. Ms. KRUPP: ...and there's a slimmer wide leg. So look how great... WINFREY: That's a perfect... WINFREY: ...who makes that pant, Ralph? Ms. KRUPP: ...she looks. KRUPP: The pant is Ralph that--and also, the coat is Gwen Stefani lamb. And I love the fact... WINFREY: Wow. Ms. KRUPP: ...that she's wearing a rocker's coat and Oscar de la Renta and Ralph Lauren. She's mixing it all up. And the key to her not looking prissy and old lady like, not that she would, but wear boots instead of a pump. It just gives more kick to your outfit. WINFREY: Wow. Mr. BOSTON: She look (unintelligible). WINFREY: You all are fantastic. Mr. KRUPP: Fantastic. WINFREY: Thank you. [APPLAUSE] BOSTON: It's all great. WINFREY: Wear boots instead of a pump. Ms. KRUPP: With a wide leg. WINFREY: In a wide leg. Ms. KRUPP: Yeah. WINFREY: Okay. We're moving on to our 40's. Meet Goldie who lost 65 pounds a few years ago. And according to Lloyd, still dresses like she's hiding something. [LAUGHTER] GOLDIE, 44: I'm 44 years old and we are here to look inside mommy's closet, right, Chloe? That would be Chloe, she's 4. Now, mind you, I've maintained the 65-pound weight loss since September of 2005. And I'm now at the section of my closet that I like to call my drop waist style section. We've got one, two, three, four, and five drop waist style because I still, I'm under the illusion that I don't have a waist. So I'm wearing one of my favorites with my favorite shoes which my husband calls my Minnie Mouse shoes. [LAUGHTER] GOLDIE: This is one that I got. And I thought I looked hot, but my husband did not. [LAUGHTER] GOLDIE: This sweater was given to me after my grandma passed away. I was in the supermarket check out stand and we were going through checking out and the lady asked me, oh, is that you're granddaughter? Well, no, it's my daughter. I have to tell you, that was a real blow. WINFREY: Oh, boy, she should burn that flower-printed thing, yeah. [LAUGHTER] WINFREY: Lloyd spent some time with Goldie yesterday. And I think, what a difference a day makes. Come on out, Goldie. Mr. BOSTON: This is my girl... WINFREY: Yeah. Mr. BOSTON: ...and she looks so fresh and young. Whoo. Yeah. [CHEERS AND APPLAUSE] Mr. BOSTON: There you go. WINFREY: There you go. Mr. BOSTON: Talk about a transformation. And I love this. She--you know what? I was so--she got me a little verklempt because she's doing the big trend that we call jewel tones. Jewel tones, ladies, work on every skin tone. Notice the great, juicy tone there. It's in jersey fabric, and that's gonna cling where she wants it and give forgiveness where she doesn't. We got her new Minnie Mouse shoes. WINFREY: Yes. Mr. BOSTON: These are fabulous ones. [LAUGHTER] Mr. BOSTON: And notice, now... WINFREY: Wow. Mr. BOSTON: ...these are Christian Louboutin, of course, and this is all from Nordstrom, here. We gave her a little clutch bag in another jewel tone. We layered it with a camisole. And she's not junking it up with a lot of accessories. WINFREY: I think it's so interesting that you used another jewel tone clutch bag and not black or burgundy, which I would have thought you would have done. Mr. BOSTON: Give it a twist. That matchy matchy bag and shoe thing will put you 10 decades behind. You wanna look fresh. WINFREY: Matchy matchy bag and shoe, 10 decades behind. Okay. Mr. BOSTON: You got it. WINFREY: Wow. I love the new hair color. Love the new hair color. [APPLAUSE] WINFREY: We'll be right back. Thank you. We'll be right back. WINFREY: Coming up, if you feel like a frump on your morning walk or even running errands around town, Lloyd Boston has a stylish trick you can do in a snap. WINFREY: We're back talking about how to look great at every age. Here's another mom who wants help getting out of the 1980's and into some clothes that make her feel good. TINA, 39: I'm now gonna be 40. I'm a stay-at-home mother. But as a result of throwing yourself into the role of mom with two young kids, you sometimes lose a little bit of yourself, your style, your fashion. When I used to actually shop for clothes and watch the fashions was back in the '80s. Don't you guys remember Bongo jeans with the nice high waist? It's really tight. And after two babies, it's really tight. And the Reebok high tops. They're so worn down now, that's slippery. And my Esprit top, the big tops, you know, remember the high waist and the big top? Those can make you look nice and thin. So you don't think it still look good or no? No go on the fashion? WINFREY: No. [LAUGHTER] WINFREY: Let's take a look at Tina one more time in her tapered mom jeans. That's a classic mom jean. Tina, come on out now. Let's see what we did. [CHEERS AND APPLAUSE] WINFREY: Whoa. So cool. Ms. KRUPP: Tina went from a mom who dressed for comfort... WINFREY: I love that. Wonderful Ms. KRUPP: ...only to someone who, I think, she could be at the hottest fashion magazine in New York. WINFREY: Yep. Yep. Ms. KRUPP: She looks amazing. WINFREY: Yeah, you do. Ms. KRUPP: And this is an example of the hot trend called chunky knit. You can be comfortable and be chic--and also, it's a flat boot. Because she is a mom, she's not gonna wear stilettos. She needs... WINFREY: Yeah. Ms. KRUPP: ...to run around in a comfortable Cole Haan flat boot. And this gives her a shape. The other thing about Tina and comfort, Oprah, she only had one bra and it was a sports bra. [LAUGHTER] Ms. KRUPP: That was the only bra she had. [LAUGHTER] Ms. KRUPP: So the first thing we did when we got to Nordstrom, we had her fitted. We got her girls up there. She has a great shape. [LAUGHTER] WINFREY: Wow. [CHEERS AND APPLAUSE] WINFREY: Send the girls up. Ms. KRUPP: It's all about (unintelligible). WINFREY: Is this from Nordstrom? This outfit is from Nordstrom? Ms. KRUPP: The whole outfit is from Nordstrom. WINFREY: That is so cute. Ms. KRUPP: And the truth that when we lifted her girls up, we found she's got a hot little bottom there.... WINFREY: Yeah. Ms. KRUPP: ...that she hasn't been playing up. And in your 30s, you can wear chunky knit and you--or age appropriate, it's really very simple. The younger you are, the more you can reveal WINFREY: Yeah. Ms. KRUPP: This is not something that someone 60 would wear. WINFREY: Yeah. Ms. KRUPP: But when you are in your 60s, you can wear a chunkier knit that's a little slimmer and more flattering. This is a whole outfit from St. John, and it fits her like a bathrobe. It's so comfortable. This is the piece that everybody wanted. WINFREY: Yeah. Yeah. Ms. KRUPP: And I loved the ruffles. It's feminine. And putting it with kicky boots make it pop and makes it edgy. WINFREY: Excellent. We love it. [APPLAUSE] WINFREY: We love it. Thank you. Love it. Okay. Susan sent us this home video from her exercise class. She's in her 40s and says she was trying to pull herself together. Let's look. SUSAN, 49: I'm 49 years old and I take an aerobics dance class. It's gym four or five times a week. I feel intimidated working out next to the younger girls who have these great bodies and their cute little outfits. I feel frumpy and old in my oversized T-shirt and boring gym shorts. I wanna know what I can wear when I'm working out that's more flattering to my body, that doesn't let all my stuff hang out. [LAUGHTER] Mr. BOSTON: I got the answer. WINFREY: All right. Okay. What's the answer, Lloyd? Mr. BOSTON: The answer is lululemon. And when you see this, it's not a vavavoom makeover. It's a real-life makeover for busy women who wanna stay fit, but sometimes have errands right after the gym. So take a look at Susan now... WINFREY: Okay. Mr. BOSTON: Because it's really clean and simple. WINFREY: Okay. Mr. BOSTON: And when you look at this, this is something that's real ife. This is real-life. WINFREY: Yes. We love that. Mr. BOSTON: So great. Mr. BOSTON: We love this. We love this. Mr. BOSTON: And I love it, too, because notice with this, it's framing... WINFREY: Oh, this is the way I love to dress. This is it. Mr. BOSTON: And again, you know the reality out there. WINFREY: Yeah. Mr. BOSTON: This is framing her fit. Notice it's sculpted around her body. And it's chocolate brown, so it's gonna be slimming without wearing morbid black. We did a shot of blush underneath. It's a halter style. So it's gonna, again, lift them up where they belong. Now, you ladies may disagree, but I'm gonna show you how to take this. If you're busy, you may have... Mr. BOSTON: ...to run right to the grocery store, you may have to catch a flight, you can certainly remove this jacket... WINFREY: Yeah. Mr. BOSTON: And the pants are almost dressy enough to make them look like something you could wear on the street. You would slip... WINFREY: Okay. Mr. BOSTON: ...on a cardigan... WINFREY: Uh-huh. Mr. BOSTON: ...in a matching color. This is how you do it. Get it in chocolate brown. You slip it on right over top. And what you do, add a fun bangle. You ditch your sneakers for a little ballet flat. Imagine a little shiny ballet flat and you can get on the plane and not look like you've been running errands. So sometimes, you only have five seconds. You can't go home and change. This is a quick way to do it if you're in a pinch. WINFREY: Put your little cardigan right in your little bag. Mr. BOSTON: Put it in your bag. WINFREY: Fantastic. Fantastic. [APPLAUSE] WINFREY: Coming up, my age group. The experts reveal inside secrets to dressing great in your 50s and 60s. We'll be right back. Back in a moment. Ms. LONDON: Here is my problem. MAMIE, 61: Okay. Ms. LONDON: You are dressing a little inappropriately for your age, my dear. MAMIE: Okay. So... [LAUGHTER] Ms. LONDON: Okay. Okay. So... MAMIE: Where is this written that you had to dress in a certain way even when you get older? Ms. LONDON: We can update your style. MAMIE: Okay. Ms. LONDON: And make it look like you are ageless and timeless and classic. MAMIE: Okay. Ms. LONDON: So I wanna make sure that things like this don't happen. MAMIE: Okay. Ms. LONDON: All right. MAMIE: Let's go. Ms. LONDON: Let's go. [APPLAUSE] MUSIC MUSIC Ms. KRUPP: Look in the mirror, tell me three words this jacket says. LINDA, 51: Timeless, classic, sophisticated. Ms. KRUPP: You know what I think? LINDA: Uh-oh. Ms. KRUPP: Dated, has no clue, cannot spend any money on herself. [LAUGHTER] Mr. BOSTON: Oh. Ouch. WINFREY: Whoa. WINFREY: Dated, no clue and... Ms. KRUPP: Does not spend any money on herself. WINFREY: Well, that was one, 51-year-old Linda whose son turned her in for a fashion update. But there is a disagreement. Linda thinks the way she dresses is age-appropriate and just fine. So I wanna see more of that. You don't have a clue. MIKE, 23: My mom likes to think that because her clothes still fit after 25 years, that that means they're still in style. LINDA: I dress classic and conservative and I also wear things that are timeless. MIKE: So something like this maternity fish dress Muumuu. [LAUGHTER] LINDA: Now, this is the dress that I think everybody should have for vacation... [LAUGHTER] LINDA: ...for hanging around. MIKE: She's also got this "Star Trek" dress here. MIKE: And I don't know where this jewel came from, but it looks like she's gonna go play "Dungeons and Dragons" after the show. [LAUGHTER] LINDA: Okay. So, this outfit--I'm not really sure. I mean, I still think I really like it. MIKE: One of my personal favorites is the traffic light or traffic sign orange dress. LINDA: My gosh. I love this. I like the way I feel this dress. I think it flatters my waist. MIKE: So I love my mom, but I'm gonna have to turn her in on her fashion sense. [LAUGHTER] WINFREY: Wow. WINFREY: Interesting. Ms. KRUPP: Shoulder pads (unintelligible). WINFREY: It's so interesting what people call timeless. Ms. KRUPP: I know. LONDON: Hmm. WINFREY: Yeah. Ms. KRUPP: I know. She thinks just because she can still wear them, it's okay. Old clothes equal old look. WINFREY: Let's see what Charla did for her. Come on out, Linda. [ CHEERS AND APPLAUSE] WINFREY: Wow. Ms. KRUPP: Whoa. WINFREY: Okay. All I got to say is, go 50s, go 50s, go 50s. [CHEERS AND APPLAUSE] WINFREY: Yeah. Wow. I mean, let's just talk about the difference in how you feel right now and the difference in the way you felt looking in the mirror with your red dress and the belt. [LAUGHTER] LINDA: Well, I thought I looked great prior. WINFREY: Yeah. LINDA: But I'm like, I'm blown away. WINFREY: Yeah. LINDA: I'm like, I feel--I just feel beautiful, like everyone is so (unintelligible). Ms. KRUPP: Oh, you are. [APPLAUSE] WINFREY: Where's your son? Where's Mike? Mike, what do you think of your mom now? MIKE: Oh. She looks great. She looks great. [LAUGHTER] WINFREY: Okay. Of course she does. LINDA: Perfect? MIKE: Perfect. Very nice, mom. WINFREY: Cool. Now, but the thing is now, you know, I think this is fantastic. Where is this from? Ms. KRUPP: This is from Nordstrom. WINFREY: From Nordstrom's. Whoa. Go, Nordstrom's. I think it--you look fantastic. What are you gonna with all those other clothes, though? LINDA: My family's sitting here, so they're going. WINFREY: They're going. Ms. KRUPP: Yeah. LINDA: I will never--no longer... WINFREY: Yeah. Yeah. WINFREY: Look at her. Ms. LINDA: I will not be able to wear those. [APPLAUSE] KRUPP: Leave them Chicago. WINFREY: This is what's so amazing. Also, look at her shape. Ms. KRUPP: She has a great shape and she was totally hiding her shape. WINFREY: Oh, my goodness. Ms. KRUPP: So the trend here is the pencil skirt. And it's a great look for women in their 50s because you put it on and it's like a shaper. It gives you that vavavaboom booty and it really is great for the hips... WINFREY: Turn around. Let's see your booty. [LAUGHTER] Ms. KRUPP: ...and the waist. WINFREY: Oh, that's a great--that's great. Ms. KRUPP: And that is a Zac Posen skirt that fits her like a dream. WINFREY: It's fantastic. Ms. KRUPP: It's a very ladylike look. It's a great look. WINFREY: You look fantastic. LINDA: Thank you. I feel it. WINFREY: You look fantastic. We'll be right back. [APPLAUSE] WINFREY: She's great. Doesn't she look great? WINFREY: Coming up, she's 61 years young and likes her wardrobe sexy. Stacy London wants to see her in a different style. MUSIC MUSIC WINFREY: I hope wherever you're watching us in this country and in any part of the world, you get some great ideas for yourself. The whole thing is that, a lot of women just get stuck. What do you do if you're getting older but you still have a body that you're proud of? Do you show it off or cover it up? 52-year-old yoga instructor Cindy wants to know how much skin is too much. CINDY, 52: I'm 52 years old. This is one of my favorite miniskirts. It's denim. It's got little sparkles in it. And I'm wearing fishnet tights. They've got a little glimmer going on there. I wear a lot of black. I feel like, this kind of shows off what I've got, if you know what I mean. My question is how to dress in a modern way that looks hip, that's edgy, that's fun, that's age appropriate? WINFREY: All right. We got the answer for you, right? Mr. BOSTON: Absolutely. I fell in love with her because she has an amazing body. WINFREY: Mm-hmm. Mr. BOSTON: I'm showing her how to show it off with silhouette, not with skin. So, there's a great way to do it over a certain age without showing all your flesh. Take a look at this. She looks like a runway diva. [APPLAUSE] WINFREY: Wow, she does. Mr. BOSTON: Right off the runway. WINFREY: Wow. Mr. BOSTON: And again, Oprah, when you look at this--now, ladies, take note. The big trend here are capes. Capes and wraps are really hot this fall. I say ladies make a huge mistake each season. They buy their coats last. Buy your coats and capes first. That way, if you can't afford a whole new outfit, you buy a cape and it makes a simple pair of jeans and a shirt look like you have whole fall wardrobe. WINFREY: Nice. Nice. Mr. BOSTON: And what's so great about it, the whole look here is from Nordstrom. WINFREY: Okay. Mr. BOSTON: It's traditional plaid tones. She's got an amazing body. Flap that front open, sweetie. There you go. That's the body you work for with yoga and you show it off with body skimming clothes and the cape floats around everything. WINFREY: Wow. Mr. BOSTON: And you can do this at different ages. And these models will show you how to do it in wearable ways. Notice my gal on the left, in that yellow? She's in her 30s. This is a modified cape/poncho. So you can belt it in and define your waist or let it out if you had dessert. WINFREY: And wear shorts. And brand new (unintelligible) shorts. Yeah. Mr. BOSTON: Absolutely. We've covered the legs and did it there. Notice in the middle, this gal's in her 40s and that look is from Saks and this is a fuller cape. It's got, kind of, a toggle feeling, like preppie. We did a little metallic, a little cheeky peek-a-boo beneath it and a fun, dark tight, as well. Thos are from Spanx and they're reversible. WINFREY: Lovely. Mr. BOSTON: Yeah. Very lovely. WINFREY: Lovely. You love yourself. CINDY: It's elegant. WINFREY: It's elegant. Mr. BOSTON: So modern. She looks... WINFREY: So modern. And modern is what you were looking for. CINDY: Yes. WINFREY: Thank you, ladies. Thank you. [APPLAUSE] WINFREY: You know, 60 looks a lot different than it did 30 years ago. One of the reasons for that is hair color, I go to tell you. [LAUGHTER] WINFREY: Rita Hazan is here. She's a famous colorist that-- I don't know how you ever are--do you have any customers 'cause you're here all the time. [LAUGHTER] RITA HAZAN: I love to help these women. And the most important thing with hair color is tone. WINFREY: Is tone. Ms. HAZAN: It change--gold, women, gold helps to keep your face looking youthful. WINFREY: Yeah. All right, meet Mamie, who likes to dress sexy and wants to know if it's working for her. Take a look. MAMIE: I'm 61 years old, today. I love to wear my skirts short. I wear my jeans tight. I wear push up bras. Majority of the time, I think they look good on me. Do you think it's something a lady over 60 should wear? WINFREY: (Makes noise). [LAUGHTER] WINFREY: Okay. Ms. LONDON: Mamie Cotton is a fiery lady. WINFREY: Yeah. Ms. LONDON: We weren't gonna take the fire out of her. WINFREY: Right. Ms. LONDON: And she felt very comfortable in her skin, so we didn't wanna take that away from her, completely. WINFREY: We want her to have that. Ms. LONDON: Exactly. So... WINFREY: We just want the push up bra and the see-through stuff Ms. LONDON: The see-through stuff was a big problem for me, frankly. WINFREY: Yeah. That's a problem. [LAUGHTER] Ms. LONDON: I'm not gonna lie. Macrame at 60 is tough. WINFREY: Yeah. Ms. LONDON: Yeah. WINFREY: Come on out, Mamie. Come on out. Let's see what we did here. [CHEERS AND APPLAUSE] Mr. BOSTON: Yeah. Oh, nice. Nice. WINFREY: Yeah, nice. Ms. LONDON: Yeah. Now, what we've done here... WINFREY: Nice. Ms. LONDON: I wanted to--the trend is ladylike dresses, Oprah. WINFREY: Yes. Ms. LONDON: And ladylike dresses for evening, for day, cocktail wear. The idea, oh, Mamie, you look great. WINFREY: Nice. Mr. BOSTON: Oh, Mamie. [CHEERS AND APPLAUSE] WINFREY: You look great. Ms. LONDON: Work it. WINFREY: You look great. You look great. Ms. LONDON: I wanted the fire color. This is Carmen Marc Valvo and it is from Saks. WINFREY: Wow. Ms. LONDON: And the idea here was that we wanted to do something where she still felt sexy. WINFREY: Yeah. Ms. LONDON: But look what we're doing. Women are afraid of pleats, okay? WINFREY: Yeah. Ms. LONDON: We're doing a couple of things, here. We're using flat pleats that make a V. We're also doing--we're raising the visual center of gravity by creating a cummerbund that's higher than her natural waistline. So when you look at her, she looks like she has longer legs. WINFREY: Yeah. Ms. LONDON: She's got this great fitting silhouette and also, these pleats are flattering because they make this V-narrowing shape. WINFREY: Yeah. You look good. Ms. LONDON: She looks good for 61, huh? [CHEERS AND APPLAUSE] WINFREY: You look good, period. Ms. LONDON: And you can do this at other ages, as well. Also note that we didn't do a deep V-neckline, here. WINFREY: Yes. Ms. LONDON: We did something a little bit more flattering. In your 40s, listen, I know, that's when things start to spread, right? Your hips, your arms start to sag, the girls go south, whatever you need to do. The idea is that this is still a flattering silhouette, still waist conscious, very Hitchcock woman... WINFREY: Yeah. Ms. LONDON: ...'40s, 1950's. All the attention is paid to the waist in all three dresses. But here, we're doing a softer silhouette on the arm. You can layer for a more complete look. We're doing a tight, here and, again, this is from Nordstrom. The whole look is by Philip Lim 3.1. And in your 30s-that's right, you better show those, girls, while you can. [LAUGHTER] WINFREY: Yes. Ms. LONDON: Right? WINFREY: Yes. Ms. LONDON: So when you get a little bit of cleavage-this is a Nanette Lepore dress and we've got a great sweetheart silhouette here. Plaid, this kind of plaid is a neutral pattern. If you wanted to a pattern type, but here, in your 30s, we've done a bare leg and a Dolce shoe. WINFREY: Fantastic. Ms. LONDON: The idea here is that you wanna who off your curves. If you pay attention to your waistline, you will always have a flattering silhouette. That is what works for women, as long as the girls are up where they should be. WINFREY: Coming up-keep the girls up. [LAUGHTER] [APPLAUSE] WINFREY: Coming up, our experts reveal some of their favorite classic looks you can wear at any age on any budget. That's next. I wanna see that, don't you? SPECIAL THANKS TO OUR FRIENDS AT SAKS FIFTH AVENUE AND AT NORDSTROM IN CHICAGO FOR THE GREAT FASHIONS YOU'VE SEEN TODAY MUSIC [APPLAUSE] WINFREY: Style experts Stacy London, Lloyd Boston and Charla Krupp have each put together a must-have timeless look. So let's see Stacy's first. Come on out. Ms. LONDON: Okay, this is the sheath dress, the frame bag, and the camel hair coat. [APPLAUSE] Ms. LONDON: This is the more expensive version. WINFREY: Okay. Mr. BOSTON: We're doing a Burberry coat here for $725, the Armani dress, $1170. That is a Bottega Veneta bag, ladies, and it is really expensive. And we are doing Miu Miu shoes for $450. Now, this look is timeless. A camel hair coat is like a trench for winter. It is a classic look. It is a nice length. It will never go out of style. It works on every skin tone. This perfect sheath dress, you can raise the visual center of gravity again with a belt if you need to... WINFREY: Uh-huh. Uh-huh. Uh-huh. Ms. LONDON: ...and that just raises the eye-line a little bit if you've got a little bit of a tummy. WINFREY: Are those fishnet? Ms. LONDON: Yeah, just baby fishnet. WINFREY: Baby fishnets. I like that. Ms. LONDON: With a peep-toe patent shoe. WINFREY: Oh, that's what you want is a baby one, and not those like-I'm going fishing this morning. Mr. BOSTON: Or I'm a burlesque star with a burlesque look. Ms. LONDON: Right, right. Here we have-the lower, or more affordably priced look from Nordstrom. The coat is Michael by Michael Kors for $268. WINFREY: That's good. Ms. LONDON: The dress is Nine West for $109. WINFREY: Wow. Ms. LONDON: And the shoes are from Enzo and they are $89. WINFREY: Very nice. Ms. LONDON: So, you can find these trends at any price point and they are investment pieces. If you have a great coat, a great bag, and a great shoe, you can pop all your old clothes into a new season. WINFREY: Love it, love it. [APPLAUSE] WINFREY: So, Lloyd, you said crisp, white shirt is a must at any age? Mr. BOSTON: Absolutely. I want ladies to feel hot and sexy at any age. And you can do animal print at any age. Now, the trick is-this is my luxury look here. Notice we got this all from Saks Fifth Avenue. This entire look is gonna be just under $6,000. Mr. BOSTON: Absolutely. And when you see the fabrics and you feel it, you'll know why. WINFREY: Wow, whose coat is that? Mr. BOSTON: Now, again-this is actually from Jean Paul Gaultier. WINFREY: Wow. Mr. BOSTON: It's a trench with feminine details along the back. WINFREY: Turn around, let's see that coat back again. Yeah. WINFREY: You could have that or a car. [LAUGHTER] Mr. BOSTON: Yeah. The coat is around three grand. WINFREY: Really? Yeah, yes. Oh, my god-used car. Mr. BOSTON: The coat's around three grand. But look what we did, we did a crisp, white shirt beneath it. Ladies, get a crisp, white shirt every season. WINFREY: Yes. Mr. BOSTON: Don't let the yellow ones come into your life. They make you feel fresh, they make you stand up straight. Knee-length, animal print skirt-I've seen ladies in their 60s work them better than women in their 20s, 'cause they've been around forever. If they do it right at the knee, you can do it with a fun gold flat. And we also have a way to do it for a lot less on a model too. WINFREY: Okay, let's see. Mr. BOSTON: So, this is a timeless, classic look. When you come in like, I own the room, you look as good as this diva who paid a little less than $400 for the whole look. [CHEERS AND APPLAUSE] WINFREY: Yeah, good. Mr. BOSTON: The trench is wearable. This is from Express, so you can get it at any mall, just about. WINFREY: Oh, okay. Mr. BOSTON: Crisp, white shirt, she's belting the waist. WINFREY: You need a crisp, white shirt. Mr. BOSTON: Absolutely. WINFREY: You must have. Turn around, can I see the coat from the back? Lovely, lovely. Mr. BOSTON: Clean and simple. WINFREY: Clean and simple. Okay? Beautiful, ladies. Thank you. [APPLAUSE] Ms. LONDON: I have to say that I love that Gaultier coat. WINFREY: Love that Gaultier coat. You can have that or a car. We'll be right back. WINFREY: Coming up, Charla Krupp is going to reveal a favorite classic look that you can wear at any age, on any budget. MUSIC MUSIC WINFREY: So let's see Charla's classic look now. Come on out. Ms. KRUPP: Oprah, nothing will take 10 years off like a pair of sexy jeans. This is Madeleine, and she is in her 50s. And you know what she said to me when I fit her in... KRUPP: ...the jeans? Yay. [APPLAUSE] WINFREY: Go 50s, go 50s. WINFREY: Yeah. What did she say? I'm sorry. Ms. KRUPP: You know what she said to me? She goes, I don't wear jeans. You know what? I didn't wear jeans until, like, six years ago, either. They are the best piece of clothing I have. But the key is the fit. They have to fit you exactly right and these Paige Denim do. This whole outfit on Madeleine is from Saks. And she's wearing a Vince leather jacket, because the older you get, you wanna spend more. Leather is a great investment. And she's wearing a Saks Fifth Avenue sweater, a Jimmy Choo sandal. The whole look here is $1,787. And then we're gonna compare her to the low end. It's still totally chic. Mr. BOSTON: Wow. FEMALE ONE: Wow. [APPLAUSE] Ms. KRUPP: And this is Keisha . WINFREY: Come on out. Ms. KRUPP: Now, Keisha's total look is $376. Her jeans are from Express. She's wearing Express sweater-the Banana Republic jacket is $168. Her shoes are from Nine West. And the trick here is you want a really sexy, high as you can stand it, metallic sandal that's really strappy because it gives you a fun evening look. You can go to a party in this. You can go out to dinner with this. WINFREY: Yep. Ms. KRUPP: This is just a great look that everyone should have in her closet. And you should update it each season with the jacket of the moment. This short, cropped jacket that goes kind of trapeze is the jacket this season. WINFREY: We'll be right back. Thank you, ladies. [APPLAUSE] WINFREY: Special thanks to the team from Rita Hazan Salon in New York City, who transformed our women, colorist Rita Hazan, hair stylist and creative director of Nexus Kevin Mancuso, and Make up artist Sandy Linter for giving our viewers age defying looks, and to all of our friends at Nordstrom and Saks Fifth Avenue, here in Chicago, we thank you for providing the perfect things to wear. MUSIC MUSIC [APPLAUSE] WINFREY: Boy, we learned a lot, right? A lot of great, great looks there. And so if you're stuck in a rut, after the show, each of our experts are going to pick their favorite audience member who's dressing best for their age. You can see who they chose on Oprah.com. More information on Oprah.com on how to make these looks work for you. Charla Krupp's new book, "How Not to Look Old," comes out in January, but you got a sneak preview today. And Stacy London's show, "Fashionably Late," premieres on TLC, November 23rd. And Lloyd Boston's book is called "Before You Put That On." Thanks and goodbye, everybody. Thank you. Really good job. [APPLAUSE] Mr. BOSTON: Thank you. Ms. LONDON: Thank you. WINFREY: Really (unintelligible). [APPLAUSE]
