Devon Windsor Dishes on Modeling, Marriage & Miami Life

By Hannah Morrill | May 1, 2019 | People Feature

Business savvy, brains, beauty—Missouri native Devon Windsor came to Miami with a plan. A plan to conquer the world. But first, there's that little thing about a wedding to the Magic City's most eligible bachelor.

devon-windsor-5.jpgBlazer, top and earrings, all price upon request, at Balenciaga, Design District.

Bring yourself back to 2008. Flo Rida’s “Low” is the song of the year and you’re at a St. Louis bat mitzvah amid a sea of nascent teens, fueled no doubt by an unholy mix of soda, Skittles and hormones. But even in the chaos, one thing is clear: One of these teens, 14-year-old Devon Windsor, isn’t quite like the others. For starters, she stands a head taller than anyone in the room. She’s long-limbed and willowy, but that’s not it. She’s also preternaturally gorgeous: blond hair, hazel eyes like saucers, and a jaw that manages to be at once soft and commanding. If there is truly such a thing as “it”—as in having “it” or not having “it” or being an “it” girl—well, here “it” was.

That was exactly the thought process local fashion photographer Suzy Gorman had when she approached Windsor and asked her to do a shoot. Gorman might as well have asked the girl if she wanted to fly to the moon. “Modeling had never even crossed my mind. I was the tallest, lankiest, skinniest girl, and in my school it wasn’t cool to be tall. I never saw myself as beautiful and I didn’t have self-confidence,” says the now 25-year-old, calling from her home in Coral Gables that she shares with her fiancé, Miami businessman Johnny Barbara. A few months later, Windsor worked up the courage to call Gorman back and arrange a session. Soon after that, she signed to a local modeling agency and started booking area gigs. She played lacrosse. She leaped 5 feet off the ground in the state championship high jump and graduated from Saint Louis Country Day School in 2012. Then, instead of heading to college with all her friends, she took a risk, and took a gap year. And that risk paid off. Windsor moved to New York City, where she was signed to IMG, one of the biggest and most prestigious modeling agencies in the world.

devon-windsor.jpgDress, $14,300, belt, $1,500, mules, $975, and earrings, $975, all at Chanel, Bal Harbour Shops.

“There have been a couple of major milestones in my career where I was like, ‘Wow, this is it. This right here is it.’ And then something else big happens. Being signed to a major agency like IMG—I thought that was never going to happen. And that happened,” she recalls, her own awe still palpable. After a string of lower-profile fashion-week catwalks, she scored a coveted spot in the lineup for Prada’s spring/summer 2014 show. Maybe this right here was it, her big break. At the fittings in Milan, most of the models had their hair and brows bleached platinum blonde. For Windsor, that shift proved to be career-changing—another break. The following seasons Windsor—striking white-blond strands, startling porcelain pale skin—was perhaps the most in-demand model of the year, walking in an alphabet soup of high-end designer shows: Armani, Balmain, Chanel. Max Mara, Oscar de la Renta, Versace.

devon-windsor-2.jpgCasitas minidress, $650, by LHD at The Webster, South Beach; Manolo Blahnik flats, stylist’s own; Celene earrings, $295, by MaryJane Claverol at The Wardrobe, South Miami.

If you’re thinking all of this came completely naturally, Windsor would politely ask you to think again. “I came into this industry with absolutely no idea what to expect. I was young, naive and nobody was there to teach me. I’d get nauseous the morning before a shoot and then I wouldn’t talk to anyone on set,” she says. “I’d keep to myself, do my job and leave. I didn’t know that if you open up, you can create meaningful relationships with these creative and amazing people. I wish I’d done more of that early on, but I just didn’t know.”

Back then, her tan and athletic frame wasn’t exactly the platonic model ideal, either. And so she worked to transform. “My job is to be a chameleon. At the time, for high-fashion shows, the whole idea was to be skinny and to fit in every sample size,” she says. “Because I was superathletic growing up, I build muscle surprisingly quickly. Pilates leaned me down, but I had to work to get there.”

devon-windsor-3.jpgPolka dot chiffon dress, $3,950, top, $450, briefs, $310, satin headband, $240, Odette bag, $1,950, nylon socks, $170, and pumps, $850, all at Prada, Design District.

Happily, before she could change too much, in fall 2013, Victoria’s Secret happened. For models, that’s like winning the lottery, 100 times over. “When I got Victoria’s Secret… that was like, ‘Holy moly.’ There’s nothing quite like walking on that runway. That’s my favorite moment of my career,” she says. Her first year, the show was at the Armory in New York City. Windsor wore red sequined hot pants, a cheetah-print bra and carried an electric guitar. She was in heaven. This was it.

Then in 2014, she got it again, this time scoring a pair of coveted wings. Windsor has appeared, in wings, every year since. “Those wings weigh 30 or 40 pounds! It’s not like light as a feather,” she laughs. “We train like professional athletes to get ready for the show. I train two-a-days in the gym six months before the show, but that’s one of the things that makes it so special. It celebrates women, confidence and being yourself. I don’t eat less. I eat more, but I eat healthier because I’m looking to build my butt muscles and get my abs in shape. I’m not trying to look like a waif. I just want to look healthy and strong and sexy, so I can feel that way too.”

devon-windsor-4.jpgDress, $14,300, belt, $1,500, mules, $975, and earrings, $975, all at Chanel, Bal Harbour Shops.

In some ways, though, Victoria’s Secret also allowed Windsor to relax. In Model Squad, the reality show that followed Windsor and company that premiered on E! this past September, she talks about not appearing in the “show packet” for the spring 2019 shows. Translation: Rather than hustling dozens of shows in New York, London, Paris and Milan, she had the luxury of choosing just one, Tommy Hilfiger, while still staying professionally relevant.

That extra time has allowed her to appear in big ad campaigns (Moschino, H&M) and to also expand her personal brand. Influencer Olivia Culpo, a close friend of Windsor’s, also appeared on Model Squad. Windsor would be the first to say she’s learned a lot from Culpo’s unfiltered presentation of her life on social media. “Influencers show a very raw, real side, and people are drawn to that. [Culpo] made me be like, ‘Maybe I want to do some of that. Maybe I want to show them what I’m wearing and how I do my hair.’ Honestly, I never thought anyone would care. But then… people do,” she says. In April 2018, she launched a YouTube channel, where fans can watch her whip up a batch of chocolate chip cheesecake bars, dangle from a Pilates reformer and curl her hair. Like Chrissy, Cindy and Naomi before her, modeling is not the end of the road for Windsor. “For the past five years, my goal has been to expand my career outside of modeling. I want to be as multidimensional as I possibly can,” she says.

devon-windsor-6.jpgChiffon asymmetric gown, $1,412, at Akris, Bal Harbour Shops; BB mules, price upon request, at Balenciaga, Design District; Celene earrings, $295, by MaryJane Claverol at The Wardrobe, South Miami; bracelet, price upon request, at Pinkgun Gallery, 786.514.3245.

Of course, she also wants to start a family. And that’s where Miami comes in. In 2016, she started dating Barbara, whose sister, Alexis Barbara Isaias, is the founder of fashion label Alexis. In June of last year, he proposed in the Bahamas, spelling out “Marry Me” on the beach, which Windsor spotted from an airplane. (You can watch this on YouTube.) The two split their time between Coral Gables, where Barbara is based, and New York, where Windsor has an apartment. “When I have to work I go and work, and then when I’m off I come to Miami,” she says. “It’s the best of both worlds. You have that outdoor beach lifestyle and the ocean, and then you have shopping and restaurants. I’ll probably always have both.” As for what’s next for Windsor, there’s a moment in Model Squad where she is perhaps the most emotional and reflective, as she talks admiringly of colleagues like Heidi Klum and Candice Swanepoel who have had children and then returned to the Victoria’s Secret runway. “It is the most badass thing! Just getting back in the game and being a supermom plus doing your own thing. I really respect women who do it all like that. That’s truly what I want for my future.”

Categories: People Feature

PHOTOGRAPHY BY RIOCAM; STYLING BY DANNY SANTIAGO; Hair by Pablo Rivera at Artist Management; Makeup by Daniela Gozlan at Creative Management using Dior Beauty