ANNA EWERS

Waist, Blond, Visual arts, Day dress, Fashion design, One-piece garment, Makeover, Stool, Fashion model, Painting, pinterest
Jason Schmidt

The roaring 20s. Versace dress, $6,675, and sandals, $1,695, 888-721-7219. Hair: Sally Hershberger for Sally Hershberger 24K; makeup: Porsche Cooper for Tom Ford beauty. 

Anna Ewers, 23, is being demographically appropriate: She's on the phone while playing ping-pong in Brooklyn's Williamsburg, the spiritual home of 23-year-old models. "I'm playing ping-pong for my workout," she says jokingly. The German-born model adds, very Germanically, "I was playing yesterday for two hours. And today I'm playing for another two hours!"

It's actually some rare time spent at home for Ewers, who in the first three weeks of the year has already logged work trips to Mexico, Barbados, and Los Angeles. Ewers's moment, launched by Alexander Wang in his Spring 2014 show, has displayed no sign of ebbing. Besides more than 100 editorials and magazine covers, she is a face of Wang, Balenciaga, and Boss, transforming from Teutonic minimalist to a comely Bardot with a sweep of eye shadow.

For the Clemente session, Ewers was very much herself—well, a Versace version of herself. When I'd suggested the idea of having her portrait done by him, she jumped at the chance. "It's so amazing that he painted me. He is a super-famous artist, so it's really cool," she says. "I think he captured me as I am," she says of her three-hour sitting. "And we took a few cigarette breaks, which was really good."

Ewers has had a long appreciation (for a 23-year-old) of art. Her favorite painting is Andrew Wyeth's haunting Christina's World. Like so many girls, she has a postcard of it bought from a museum store. "I don't know why I love it so much," she says."It's just an amazing painting." She also has a love of Sebastião Salgado's photography. "I go to museums to look at things, and I get lost."

"I can also drink a lot of coffee and sleep afterward, I think it's because I'm young."

Her 20s, so far, have been working out just great. "They've probably been the most exciting years of my life. A lot is going on." While she's more established, she's simultaneously more hectic. "I am getting more and more work, but at the same time I'm getting into the rhythm and getting used to traveling so much." She adds with the lightest boast, "Oh, I can sleep whenever, wherever." What about coffee? "I can also drink a lot of coffee and sleep afterward. I think it's because I'm young." (Insert a yelp from every thirtysomething woman on earth.)

In a relatively short career, there have been many highlights. "My first Harper's Bazaar cover!" Ewers prudently notes of her debut on our pages last year. "My first Balenciaga show. My first Prada campaign, because it was my first big campaign. And my first Alexander Wang campaign, which was definitely the most exciting one because I was just starting out, and I was like, 'Whoa, this is amazing.' "

Ask about an older woman Ewers admires and she rather adorably replies, "Daria Werbowy [who is 32]. She's supercool, she's not too much on social media, and I don't think she cares too much about fashion—like I don't." Ewers has yet to meet Werbowy, "but her career is impressive, and she's super chill."

Ewers's style is also super chill. She wears a lot of Alexander Wang, as she is close friends with the designer. "Too many navy and gray cashmere sweaters!" she says. "It's a problem." A night out, and she's in "a little black dress, black heels, a little eye, and a cute lip." Skin care? "I love Weleda. It's German. It's good." Favorite destination? "My dream is to go to Mongolia. I'm going in August. I need to go to places that are wilder than Paris, Milan, and London." And, finally, favorite meal? "Spaghetti Bolognese. I shouldn't eat it often, but I eat a lot of it." Ah, the joys of being 23.

LIYA KEBEDE

Purple, Magenta, Visual arts, One-piece garment, Fashion design, Stool, pinterest
Jason Schmidt

Purple reign. Tom Ford dress, $8,780, similar styles available at Tom Ford New York, 212-539-0300; Proenza Schouler shoes, $995, 212-420-7300;  Coat and earrings, Kebede's own. Hair: Miki at Whittemore House Salon for Kérastase Paris; makeup: Rommy Najor for Dior Addict.

Liya Kebede has been modeling for more than 20 years, but she had never before sat for an artist. It was a particular thrill to sit for Clemente. "I didn't know his work specifically, but when I found out that he had painted the portrait of Gwyneth Paltrow in [the 1998 film] Great Expectations, I was so excited," she says. "I remember when I watched that movie, the portrait really touched me. I don't know why. Then to suddenly see my portrait done in the same way, it meant a lot to me."

It seems ironic that Kebede, 38, has never been painted, given her precise, delicate features. "The relationship with a painter is so different," she explains. "He's so focused on you, and you're always wondering, 'What could he be looking at?' It's so penetrating. There's something quite beautiful about it." Kebede posed in a glorious Tom Ford evening gown, but in the cold of the studio covered her knees with her winter coat. So Clemente couldn't help a little bit of subversion, adding the coat to the final work. "He said, 'It will be the one thing in the picture that's yours—it brings it all together.' "

When Kebede was growing up in Ethiopia (where she returns twice a year for her clothing line, Lemlem, and her work for her maternal health foundation), art wasn't readily available to her. But she was ahead of the curve in other respects, having had her two children, Suhul and Raee, by the time she was 27. Now separated from her husband, Kassy Kebede, she says, "My 30s have been a really transformative decade. I feel like I've grown a lot." However, she's lived a lot, early. "Children make you grow up very quickly," she says. "You become a mom, so you have to be a mom, you know?" But today, with a 10-year-old and a 15-year-old, she is officially a cool mom. "I'm having a fun relationship with them right now," she says, adding with a laugh, "I hope it's nice for them too!"

"I love women who do their thing, who aren't caught up in the superficiality of things."

Kebede was only 15 when she started modeling, originally spotted by a French agent in her hometown of Addis Ababa. She finished her schooling before moving to Paris, where she caught the eye of Tom Ford, who put her on an exclusive for Gucci and also in campaigns for Yves Saint Laurent. Alongside innumerable magazine covers, she was named a face of Estée Lauder in 2003, and became a L'Oréal ambassador in 2011. Today she works closely with Nicolas Ghesquière at Louis Vuitton and occasionally still hits the runway for designer friends like Proenza Schouler. Fashionwise, she's never been one for trends. She refuses to wear "dresses you're trying to figure out! I gravitate toward men's sweaters. I love men's sweaters, men's pants—I love all that stuff."

The naturally lean Kebede keeps herself so with an everything-in-moderation lifestyle and regular attempts at yoga. "I have a problem fitting it into my life," she says, noting the quirks of her travel schedule. "You know, when you're jet-lagged and you're like, 'Should I sleep or should I get up and do yoga? I think I'm going to sleep.' "

As she gets older, Kebede hopes to meet more women "who embrace their age and imperfections. I love women who do their thing, who aren't caught up in the superficiality of things. In the world we live in, that's harder and harder to find. We need to feel more secure in ourselves. When you look at Hollywood and what it's projecting at us about how you have to look," she says, sighing, "one wrinkle is such a big deal." And while less prevalent than before (see this portfolio for evidence), ageism in the model business is ever lurking. "Being in an industry where image matters," Kebede observes, "it's definitely challenging for me."

Sure, but currently she doesn't seem to have a wrinkle. "The minute you get one, let me know," I say. "Har-har," she replies. "We'll have a big chat about how to handle it."

CHRISTY TURLINGTON

Dress, Art, Temple, One-piece garment, Visual arts, Costume design, Victorian fashion, Vintage clothing, Painting, Sculpture, pinterest
Jason Schmidt

Portrait of a lady. Valentino dress, $16,900, 212-355-5811; Valentino Garavani sandals, $1, 495; Hair: Sally Hershberger for Sally Hershberger 24K; makeup: Dick Page for Shiseido.

She's been adept at hiding it, but Christy Turlington suffers from a terrible affliction: a "gimpy" eye. She's soldiered on despite this impediment—achieving 30 years of supermodel-dom, plus a second, even more super life as a global maternal health advocate. "Someone once said I have a symmetrical face," she says. "I do not have a symmetrical face. Almost nobody does. But, yeah, I have a gimpy eye. One eye that's round and one that's more slanty." She laughs. "I'm sure it's a sign of intelligence." She adds, "In a photo session, people try to balance my eyes with light." But not Clemente. In her portrait, "one eye was as it is in life, which I love. I can see a lot of things that are me." That said, "he added a few inches to my neck!"

Turlington first sat for the artist 20 years ago. "It was a watercolor; I have it in my bedroom. It was more of an impression—we knew each other, but time makes such a difference." She sighs. "Now we're at the place where everything is 20 years ago. We were laughing about that, and then we said, 'Okay, every 20 years we'll do a sitting.' So we made a date."

On viewing the completed portrait, Turlington says, "It has the feeling of Pontormo or Modigliani or Giacometti. All portrait artists that I love. You know, I like Lucian Freud, but I don't know if I would, say, run to that sitting."

At 47, Turlington is in fine fettle. She works full-time on her nonprofit, Every Mother Counts; is raising two children, Grace, 12, and Finn, 10, with husband Edward Burns; and still makes time for the occasional high-profile modeling gig (besides regular magazine covers, she has contracts with Maybelline and Calvin Klein, among others).

Of the changes in the industry—the birth of the social supermodel, for example—she observes, "In the '80s or '90s, the supermodel thing was kind of similar; it brought more sales, more attention. Then that becomes exploited, and everybody hates those people. When an era ends, there's nothing worse than having been tied to that era."

"But yeah, I have a gimpy eye. One eye that's round and one that's more slanty."

That's why, of course, Turlington did other things: completing a bachelor's degree with honors, studying public health at Columbia, and attending various wellness initiatives before the 2010 launch of Every Mother Counts. "The more you have going outside of the modeling world, the better off you are," she says. "You can't be reliant on the flavor or the tastemakers, you know?

Turlington has managed to transcend fashion while remaining very much in fashion. "I'm not one to think that much ahead of myself, apart from the fact that I love 50. It looks pretty; it's aesthetically pleasing," she says, laughing. "All the good things in my life happened post 30. But I guess you're always in a state of becoming. I love the pictures Alfred Stieglitz took of Georgia O'Keeffe. He photographed her over and over through the years, so he had this portrait of her that wasn't just a moment; it was all the parts of her over time. I kind of see it like that."

Asked to name her aging inspirations, Turlington says, "There are so many. Joan Didion. Come on! I love her. Vanessa Redgrave. Gloria Steinem! Charlotte Rampling! Iman, I mean, come on." She's a particular fan of Didion's style. "She never changed, and she looks perfectly modern." (Like Didion, Turlington plans to embrace the turtleneck. "Céline, old Helmut Lang, skinny Calvins," when the time comes.)

Until that fateful day, Turlington remains a model of health and balance (thankfully, she also possesses a deep love of red wine). She is currently finishing a month-long cleanse. "I don't really crave things," she explains. She has also started training for the Boston Marathon, in April. "My fifth marathon since I turned 42!" she chirps. Along with her regular yoga, Turlington will often run for up to two hours at a time. "Just to chill, do my long run, and breathe."

I read her a quote from Gwyneth Paltrow, who said that turning 40 was like getting a "software upgrade." "Oh, you girls in your early 40s," she cackles. "You should see what it does to your hard drive."

LINDA EVANGELISTA

Clothing, Window, Shoulder, Dress, Style, One-piece garment, Waist, Bag, Fashion, Day dress, pinterest
Jason Schmidt

The artist's supermodel. Dolce and Gabbana dress, $6,495, and shoes, $895, 877-70-DGUSA; Hair: Sally Hershberger for Sally Hershberger 24K; makeup: Dick Page for Shiseido. 

Linda Evangelista is describing the images she has of herself—among other things—on the walls of her New York apartment. "Pulling my cheeks from Steven [Meisel], crying from Peter [Lindbergh], whistling from David [Sims], the corset …"

Of course, even with the briefest description, you can see each and every picture. Evangelista is, after all, the supermodel's model. She wrote the book on chameleonic glamour (sadly, not yet literally, much to the chagrin of Linda obsessives everywhere). But while she has posed for the lexicon of photographers, illustrators, magazines, and campaigns over a legendary 35-year career, Evangelista had never sat for a painter.

It's funny to hear the superest of supers say she was "nervous. I kept saying to myself, 'Linda, he wouldn't have accepted to do this if he didn't like you.' " She continues, "When I first sat down, Clemente said, 'You really want to wear that dress?' And I was like, 'Yep, this dress is me.' I'm very Dolce, very 1950s. I love womanly embellishment. But I didn't know it would take five hours!" She laughs. "With my elbow out. Oh, my God." In Clemente's portrait, Evangelista sees an "exaggerated version of myself. I was shocked! But I thought it was beautiful. And I never think anything is beautiful."

Evangelista, who turned 50 last year, characterizes this new decade with a wry humor. "I'm managing." The best part? "The wisdom. That sounds very cliché, but it's true. If only I had this wisdom 30 years ago." Worst? "It's fucking work! And you can quote me on that. I have every gizmo and gadget and tool from Spinning bike to Power Plate to Bosu ball to rowing machine and stretching bands and this and that." A trainer visits Casa Evangelista five times a week. "For 15 years! And he's cute," she jokes. "So that helps."

"My agents had an intervention where they made me sign up for Instagram."

Evangelista is, yes, super diligent with her upkeep. "Today I started with a Greek yogurt, and I put some chia and hemp in there and blueberries. I try to have my carbs midday, and at night I love vegetables. Love, love, love vegetables. I'll have a protein with veggies." She's not a drinker. "Nope. I like wine; I love pairing it. But I don't drink, no."

For skin care, she swears by uptown New York facialist Georgia Louise. "She has magic hands! I also exfoliate a lot, and I'm a big freak for sunscreen." To wit, Evangelista's Instagram often features her swaddled in protective summer garb that gives her an air of Garbo. When she's dressing up, she swears by the ageless allure of "anything Azzedine Alaïa."

Ask what older woman she admires and her answer is swift and hilarious: "There's not many older than me! But … Iman. She's just fabulous. She's a role model to all of us. A gorgeous person."

Like Iman, Evangelista has embraced social media. Well, begrudgingly. "I was forced! My agents had an intervention where they made me sign up for Instagram. And I post, but I don't want to share that much. I don't know what to share." She's an avid follower of the social models Cara and Kendall and Gigi ("I think they're all fabulous"), but believes that if social media had existed in the supermodel era, "I don't think we would have needed it."

Now that she's in this brave new cyberworld, does Evangelista obsess about what she posts, how she comes off, how she looks? Does the ultimate model have a selfie face? "No, no," she coos reassuringly. "I don't need one."

IMAN

Floor, Flooring, Art, Street fashion, Long hair, Paint, Visual arts, Painting, Portrait, Modern art, pinterest
Jason Schmidt

On Iman: Salvatore Ferragamo dress, $1,950, 866-337-7242.

The first model to sit for Clemente's series was Iman. Sadly, due to the death of her husband, David Bowie, she was unable to complete the photo session. While we included her portrait here, it says everything about her that each woman in this portfolio, when asked who they admire, said "Iman."

This article originally appeared in the April 2016 issue of Harper's BAZAAR.