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How Brandon Maxwell Overcame His Insecurities and Conquered Fashion

Brandon Maxwell arrives at his Midtown Manhattan office late on the Monday morning after the Super Bowl, right off a flight from Houston and a sleepless night. He has not taken a single day off in six weeks—during the previous one, he flew to Los Angeles and back twice for red-carpet fittings—and his fall runway show is less than eight days away. He is still wearing an Adidas tracksuit embroidered with his name, a gift from Lady Gaga for styling her well-reviewed halftime performance the night before. But he seems to be in no mood for a compliment.

“Getting my picture taken or having someone say I’m great really means nothing to me,” he says as he launches into an unexpected lament of his own rapid success. “Maybe I’m tired and I’m sounding really bitter,” he adds. “I don’t mean to at all. It’s just that everyone puts this immense pressure on you to be the Next Big Thing, and I have to sit back and ask myself, ‘Does that matter to me?’ Because at the end of the day they just sit there waiting for you to fall. It’s 2017—we live for the fall!”

While you would be hard-pressed to find anyone in fashion who actually isn’t rooting for Maxwell, a self-trained designer who wowed the industry two years ago with his exquisitely tailored, full-drama gowns, there is some truth to what he says. Hot designers come and go, a fact of life he witnessed while working behind the scenes as a celebrity stylist for years before he stepped into the spotlight with his own collection, which has been an absolute hit with stars like Nicole Kidman, Kerry Washington, and Gaga, of course.

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“I’ve watched this movie a million times,” Maxwell says. “I know how this story goes. It will go down.”

But in spite of his pessimism and neuroses, or possibly because of them, something about Maxwell’s humility suggests things may end differently for him. For one thing, he works harder than he really has to.

At the CFDA Awards last June, when he won the Swarovski Award for breakthrough womenswear designer after only two seasons under his belt, he exposed his insecurities with endearing candor onstage in front of some of the most intimidating names in the industry (Beyoncé, Naomi Campbell, Donna Karan, Calvin Klein). “I am a slightly overweight boy from Texas whose idea of a fine meal is something that is rolled up into a ball, deep-fried, and put into wax paper,” he said. “I really was very gay in a very small town, and I only had the women in my life to stay with me on the weekends and make me feel normal. When they let me dress them up and take their pictures, it gave me a purpose in life, and it made me feel like I could get by.” What he didn’t seem to realize was that pretty much everyone in the room could relate to that sense of being an outsider, because they were all once nobodies from nowhere.

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Maxwell is 32 years old, has salt-and-pepper hair, and is more handsome than he probably realizes. He lives in N.Y.C.’s Greenwich Village with a French bulldog named Stella. He drives a Range Rover. He is private about his dating life, but he is in a serious relationship with his best friend since college, and that—as much as anything—seems to be lightening his mood. If he could, he would eat Mexican food three meals a day. He has a fear of heights and of not being able to pay his rent. He hates pesto. He loves New Jersey because the strip malls are filled with chains like Target, Bed Bath & Beyond, and Chili’s, which remind him of his hometown of Longview, Texas.

“There was nothing to do in my town,” he says. “Growing up, I drove a lot and listened to music. It’s the only time that I feel really peaceful. Sometimes you need to go to Chili’s, you know what I mean?”

Maxwell is the oldest of five children. His parents, Mike Maxwell and Pam Woolley, were divorced when he was 7, but his sister, Kady, and their half-siblings, Dylan, Ben, and Bianca, are so close that they consider themselves “soul siblings.” His family owned a beer, wine, and liquor distributorship, but it is his maternal grandmother, Louise Johnson, who often comes up first in Maxwell’s stories about his youth. “Mammaw, that’s what I call her,” Maxwell says of Johnson, who was a buyer for Riff’s, a bygone specialty store catering to stylish women made wealthy by the oil boom in East Texas, and where little Brandon rushed to pretty much every day after school to watch her work. Johnson sells clothes from her home to this day and continues to inspire Maxwell.

“I grew up in a dressing room,” he says. “When a customer came into the store, my grandmother laid out every possible bag, shoe, and dress for her to choose from. I think that’s really where I learned how to be a stylist. It gave me a very practical approach to clothing.”

Maxwell’s début collection, shown in the mirrored dining room of disco-era New York restaurant Mr Chow, was a distillation of those women he had known in his youth, combined with all the knowledge that followed from years of failures and successes, of working alongside Gaga and styling real-life magazine editorials. Critics saw in Maxwell’s sleek, sensual dresses the second coming of Halston, once the preeminent designer of American fashion, who came from Des Moines, Iowa. “That’s the nicest compliment ever,” Maxwell says of the comparison. “It’s just very strange that I grew up eating McDonald’s every day and that I would be in the same sentence as Halston.”

That first collection was born from what Maxwell calls a “dark moment” in his life that inspired him to take a now-or-never creative risk, locking himself in a studio alone with music to work through his pain. “The only way I have ever been able to communicate is by creating,” he says. And while the results were phenomenal—Gaga herself came to support Maxwell at his New York Fashion Week début—his doubts remained.

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This year, in the days between the Super Bowl and the presentation of his fall collection, he again faced those demons, only this time he allowed himself to “let go of what I think people want from me,” as he wrote in a short letter he included with his show notes. He went further than he ever had before to define his style as not just glamorous but ferocious, with stunning dresses in fuchsia and teal, an enormous fur chubby, and a silver power pantsuit that glittered as his models walked to “Man! I Feel Like a Woman!” People loved it all over again.

“Really, all I wanted to say is like, ‘Hey, guys, is it cool with you if I break out a little bit?’ ” he says. “Maybe what I learned is that the perception everybody else has of me is not the perception I have of myself, which was that I felt sort of locked in a box of black-and-white suits and minidresses.”

When we next speak, in March, it is shortly after a photo shoot for this story in which Maxwell pays tribute to an iconic visual of fashion fierceness: the ’80s videos for “Simply Irresistible” and “Addicted to Love.” Although Maxwell has to be coaxed into taking on the role of Robert Palmer, he is happy with the results.

“I don’t think you can find a single photo of me that is not in black-and-white, looking very serious and sort of hunched over,” he says. “This is the first time I’ve ever let myself do something like that, which seems really out of control to me. But when I look around, that photo really embodies the spirit of the women who are in my shows and how we feel when we’re making them. And I think it also embodies how I’m feeling right now. I am the boy who wants the girl with the big hair to come out and dance to Shania Twain down the runway. That’s what makes me happy.”

In fact, Maxwell sounds uncharacteristically upbeat. After months of nonstop work, he has finally allowed himself to take a break—a vacation in St. Barts and Anguilla right after the show, and then a road trip through Texas. He has just gotten off the plane, and he can’t wait to tell the world that he and his boyfriend got engaged on the trip.

“I was driving down the highway in Texas last night, eating a Dairy Queen Blizzard, sitting there with a ring on my finger,” Maxwell says. “I was just like, ‘Wow, this is pretty good. This is great.’”

For more stories like this, pick up InStyle's June issue, on newsstands and available for digital download May 12.