Photo: Marc Royce

17, Singer + actress

The multitalented teen had her breakout moment in 2010 when she starred as Rocky Blue in the Disney Channel series Shake It Up. Last year she released a self-titled debut album, which features the platinum-selling single "Replay." Her latest project is the Disney Channel movie Zapped, out this summer.

Go-to outfit: "I like to take feminine clothes and mix them with tomboy street-style pieces," she says. "Cute, comfortable things like sweatpants that you can dress up or down with heels or sneakers."

Style crush: For Zendaya, it's about civilians, not celebrities. "A lot of my fashion inspiration comes from my friends or random people on Instagram. Nothing matches or makes sense, but it works because they have confidence in their look."

Fashion regret: "A long floral dress I paired with booties. It wasn't very flattering—I hadn't gotten that far in my style evolution yet. I was 13 at the time, but still."

Advice she'd give her younger self: "I am my younger self now! But I'd say don't try to grow up too fast. Enjoy being 11, because one day you'll be 18, and you'll have your time to be grown-up then."

Sweatshirt, ICB. Shirt, Thomas Pink. Jeans, Bebe. Bracelet, Orly Genger by Jaclyn Mayer. Watch, Rolex. Shoes, Schutz.
beth behrs

Photo: Marc Royce

Beth Behrs
28, Actress

On the hit CBS sitcom 2 Broke Girls, Behrs plays Caroline, a former Manhattan heiress who's forced to become a diner waitress after her Madoff-esque father loses his fortune.

Go-to outfit: "I'm a big fan of blazers," says Behrs, who favors Ralph Lauren, J.Crew and Alice + Olivia. Her most recent obsession? Ryan Gosling–print leggings that a writer on the show gave her. "I have to find the right blazer to rock with them."

Style crush: Blake Lively. "She's classic, chic and comfortable in her own skin."

Fashion regret: "A poufy, pink, one-shouldered dress and big Frankenstein hair that I wore to a party a couple of years ago. I knew when I was leaving the house that it wasn't right, but it was too late to change. It was like prom in the '80s."

Advice she'd give her younger self: "If you're uncomfortable, you're going to radiate that. Remember, it's your body and you can wear what you want."

Jacket, MSGM. Romper, Rebecca Minkoff, 866-838-6991. Necklace, Lydell NYC. Bracelets, Cara Croniger, 212-334-4964.
jamie chung

Photo: Marc Royce

Jamie Chung
31, Actress

Currently starring as Channing, a member of a shadow organization on NBC's science fiction drama Believe, Chung can also be seen in The Hangover Part II and III and the upcoming Sin City: A Dame to Kill For.

Style philosophy: "I love mixing prints and being a little loud," says Chung. "But now that I'm in my 30s, I try to do what my mom says, which is keep it classy. If you're wearing something sleeveless, pair it with something longer."

Fashion regret: "Handkerchief tops! I remember one I wore to someone else's junior prom. It was iridescent and had multiple colors and a matching high-waisted skirt. It was my own design, so I have no one to blame but myself."

Advice she'd give her younger self: "Listen to your gut. Whether it's dating the wrong guy or making a career decision, your first instinct is usually right."

Blazer, Kate Spade New York. Bralette, Milly. Beaded skirt, Adrianna Papell. Bracelets, Lizzie Fortunato. Necklace, Showrowk. Shoes, Jerome C. Rousseau, 416-975-1810.
daisey fuentes

Photo: Marc Royce

Daisy Fuentes
47, TV personality + entrepreneur

Hired as MTV's first Latina VJ in 1993, the TV host and model has had a lucrative second act with a hugely successful line (which just celebrated its tenth anniversary) of clothing, accessories and home decor for Kohl's.

Go-to outfit: "I love keeping my core look simple—skinny black pants and a T-shirt—and adding an amazing jacket and boots or a great scarf," says Fuentes, whose favorite designers include David Meister, Michael Kors and Max Azria.

Style philosophy: "The late '80s and early '90s was a good era for experimenting. But now is not the time for me to be daring with fashion. I like trends, but I don't wear all of them, and I adapt them to my age and personality."

Fashion regret: "It was a black dress I wore to an MTV awards show that was both embellished and sheer. You could see half my ass."

Advice she'd give her younger self: "Don't be so hard on yourself and others. And try to live in the moment. Otherwise, you'll miss it."

Dress, Sportmax, 212-674-1817. Jewelry, Daisy Fuentes for Kohl's. Shoes, Jason Wu.
melissa Leo

Photo: Marc Royce

Melissa Leo
53, Actress

The award-winning Leo (she won the best supporting actress Oscar in 2011 for her role as the tough-loving, chain-smoking mom in The Fighter and an Emmy in 2013 for her memorable guest appearance on Louie) played attorney Toni Bernette on HBO's Treme. She will next be seen in the film The Equalizer in September.

Go-to outfit: Though she describes her personal style as "boyish and raggedy," Leo says she's gotten a crash course in fashion by "going to events where I'm expected to be a movie star." Her take-away? "Simple is better. I love a pencil skirt, asymmetrical tops make me look crooked, and I'm very high waisted, so '40s- and '50s-style clothes fit me well."

Style crush: "Kate Winslet is a great hero of mine. She has such a gracious way of presenting herself. She's not a stick-thin woman, and anywhere she goes, she turns up looking like a lady."

Advice she'd give her younger self: "Aging is a blessing and should not be shunned. This is the great gift of getting a little older: knowing how to behave, what to wear, and when to wear it."

Vest, Alvin Valley. Skirt, Antonio Berardi. Earrings and cuff, Elizabeth and James. Shoes, Pierre Hardy.
beveryly johnson

Photo: Richard Majchrzak/Studio D

Beverly Johnson
61, Entrepreneur + actress + model

The first black woman to appear on the cover of American Vogue, in 1974, former supermodel Johnson has since made numerous film and TV appearances (including her 2012 reality show, Beverly's Full House, on OWN) and currently has a hair extensions line, available at BeverlyJohnson.com.

Go-to outfit: "I wear a lot of formfitting styles because I feel good in them!" says Johnson, who favors looks by Dolce & Gabbana and Ralph Lauren. "I don't like to be overtly sexy with cleavage, but I like to try things I probably shouldn't be trying, like short dresses. My daughter can attest to that."

Style crush: "I'm a big fan of Kim Kardashian. I think she's very dedicated to fashion. I love her big coats and fitted dresses."

Fashion regret: "No regrets. I remember those Versace bondage dresses with the big gold buttons. They were so '90s and so fun! I love how everything comes back again, like the '70s jumpsuits that are big now. I wish I'd saved mine, but there's no way I could fit into them now."

Stay-strong secret: "Learning something new and being passionate about a project keep you young. Even if you aren't as mobile as you once were, you still have a brain, and the way to honor longevity is to keep using it."

Advice she'd give her younger self: "When your second husband says he's thinking about an open marriage, believe him."

Dress, Dolce & Gabbana. Bracelet, Alexis Bittar. Shoes, SJP.
jessica walter

Photo: Marc Royce

Jessica Walter
73, Actress

Veteran stage and screen actress Walter, best known for playing the hilariously caustic matriarch on Arrested Development, is currently the voice of alcoholic spy Malory on the animated FX series Archer and will star in the upcoming TV Land comedy Jennifer Falls.

Go-to outfit: Jeans, a button-down shirt and sneakers. "It's all about comfort," she says. "I like James Perse blouses because they fit me well. And Coldwater Creek has good jeans that come up to the waist for us grown-ups. I don't like low rise because my muffin top plops over."

Fashion regret: "I have a few really expensive things I bought last minute for awards shows and never wore again."

Advice she'd give her younger self: "I'd say, 'Self! Relax. Chill. It's okay.' I think people who are stress-free stay younger. And take care of your skin, no baking in the sun. Those days are over."

Blazer, Escada Sport. Top, Eileen Fisher. Pants, Theory. Earrings, Lizzie Fortunato. Necklace, Alexis Bittar. Shoes, Boden.
tippi hedren

Tippi Hedren
84, Actress + activist

Most famous for her film debut in 1963's The Birds (she still includes little drawings of birds as part of her signature), Hedren is also the founder of the Roar Foundation, a nonprofit educational organization that supports the Shambala Preserve, an exotic-animal sanctuary in Acton, California.

Style philosophy: "It's fun to dress now. We were stuck in so many rules in the past! Now you can be more creative and go to a cocktail party in skinny jeans, a great top and heels."

Go-to outfit: "I like dresses with straight skirts, not full, because I'm short. Jeans. And I found this really wonderful jacket at Bebe that's black and short and faux leather. Every time I wear it, someone wants to steal it from me."

Stay-young secret: "I eat a lot of fish and vegetables, avoid meat and bread, and work out every morning. And I'm working all the time for Shambala. Having a goal keeps you vibrant and healthy and alive."

Jacket, 1. State. Top, Diane von Furstenberg. Skirt, Adeam. Earrings, T+J Designs. Cuff, Robert Lee Morris. Shoes, Brian Atwood, 212-753-4000.
tao porchon-lynch

Tao Porchon-Lynch
95, Yoga instructor + dancer

A yoga devotee for most of her life (she started practicing when she was 8!), former model and actress Porchon-Lynch founded the Westchester Institute of Yoga in New York in 1982. In her spare time, she's a competitive ballroom dancer.

Go-to outfit: "I like to wear anything beautiful. But certain things are not my style: I can't stand sneakers; I always wear heels. And I don't like ragged jeans."

Fashion regret: "None! People tell me you can't wear sexy tango dresses when you're old. Nonsense. There is nothing you can't do."

Stay-young secret: "Learning how to breathe properly is important," says Porchon-Lynch, whose DVD Yoga with Tao Porchon-Lynch is available at YogawithTao.com. "You have energy that lies dormant inside you, and you awaken it by breathing correctly."

Advice she'd give her younger self: "Don't dwell on anything negative, don't procrastinate and live for today."

Leather jacket, Elie Tahari. Shirt, Tommy Hilfiger. Pants, Elie Tahari. Earrings, Ben-Amun. Necklace, Shourouk. Rings, Carelle. Shoes, Banana Republic.
agnes zhelesnik

Agnes Zhelesnik
100, Teacher

Believed to be the oldest working teacher in America, Zhelesnik is a full-time home economics instructor at the Sundance School in North Plainfield, New Jersey, where she's been employed since 1995. Nicknamed Granny by her students ages 3 to 6, she still teaches four classes a day. "If you met the kids, you'd go to work every day, too," she says.

Style philosophy: "I think people should be appropriate. Sometimes when I see an older person with a short dress, I say, 'I don't think that looks so nice.'"

Go-to outfit: Jeans and sweaters. "Now I don't wear anything very fancy. But at one time, I wore fussy clothes—high heels and circle skirts and nice dresses—and liked them very much."

Fashion regret: "I don't regret anything, because everything I wore I picked out myself."

Stay-young secret: The schoolchildren. "They are the best. I feel the love they give me. They come in before and after school and hug me. I like the attention."

Anorak, Marla Wynne. Top, Tanya Taylor. Skirt, Lela Rose. Bracelet, Aerin Erickson Beamon, 646-619-6857.