Willa Bennett, the editor in chief of Cosmopolitan, has quickly distinguished herself not only through her leadership but through her distinct and polished personal style—one rooted in classic menswear. Known for regularly wearing suits and ties to the office, Bennett’s sartorial identity has become integral to her public persona. Vogue highlighted her impressive tie collection, while a 2024 New York Times profile noted how often she dons a full suit and tie at work. Her tailored wardrobe choices are far from superficial—they reflect a deeper self-expression. She owns approximately 170 ties but regularly rotates only a few favorites, including a black Ralph Lauren tie embroidered with her initials, and selections from Drake’s and Hermès.
Speaking from her office in the Hearst Tower, which also houses Esquire, Bennett enthusiastically discusses her affinity for menswear. She describes how she intentionally seeks out pieces like a vintage Celine suit she had custom tailored, explaining that this style is authentic to her, not curated for social media. Her conviction is simple and clear: “It’s how I want to dress instead of pretending how I want to dress.”
As the leader of Cosmopolitan, Bennett’s style reverberates beyond her own wardrobe. Her influence shapes the fashion sensibility of millions of readers each month, particularly Gen Z. She acknowledges that her menswear-driven aesthetic may inspire younger audiences to explore suiting and ties in unexpected ways. For Bennett, menswear is not just a preference—it’s a lens through which she sees and interprets style.
Her journey into menswear is rooted in her formative years. Raised in Los Angeles, Bennett trained as a ballet dancer and later attended Sarah Lawrence College on a dance scholarship, double majoring in journalism. It was during this period that she began to embrace men’s clothing. As a queer ballerina moving from a world of hyper-femininity to one of structured suiting, adopting the tie became a form of personal rebellion. She reflects that wearing a tie was the most subversive thing she could do—it was a punk-rock move of self-definition.
After graduating, Bennett’s career path took her to New York City, where she held roles at Seventeen and the Bustle Digital Group before entering the men’s fashion sphere. She managed social media for GQ for over two years before becoming editor in chief at Highsnobiety in 2022. During her tenure there, the publication won a National Magazine Award for General Excellence. In 2024, she returned to Hearst to take over Cosmopolitan and Seventeen.
The interview took place in April at the Hearst Tower. Bennett, with coffee in hand, sat behind her desk surrounded by framed vintage covers of Cosmo. When asked about her caffeine habits, she admits to drinking coffee “all day,” a routine that began during her intense college years as a double major. Her passion for ballet still lingers, as she recalls loving performances by choreographers like Kyle Abraham and Emma Portner, while also affirming that Swan Lake remains one of her favorites.
Menswear has long been a central point in Bennett’s conversations—even with romantic partners. Her love for traditional men’s tailoring regularly spills into all her creative expressions. She recounts how, even in choreographing dance performances during college, she dressed dancers in suits and ties. Ralph Lauren, in particular, served as a longstanding influence. She praises his commitment to masculine silhouettes and traditional tailoring, describing his style as a timeless blueprint.
When asked what young men today care about in fashion, Bennett notes a shift toward feeling good in clothes and an increased concern with garment quality and origin. She points out that younger generations are more reflective, learning from discomfort and seeking authenticity in what they wear. For her part, Bennett hopes to use Cosmo’s platform to advocate for freedom in personal style—encouraging people to dress in ways that reflect their true selves, regardless of what marketing might suggest.
Bennett’s tie collection is more than a hobby—it’s a way of capturing memories. While she has her go-to pieces, others she wears once and keeps as tokens of specific times in her life. She often buys ties while traveling for Fashion Week, frequently visiting vintage stores or scouring eBay. Her eBay strategy includes purposefully misspelling brand names like Dior to uncover hidden gems—an insider trick she and her friends often use.
Her father also played a role in shaping her interest in clothing. Although his taste is bolder and more playful than hers, he shares her appreciation for vintage garments. Bennett’s own style leans more toward the classic, while her father, for example, happily wears the hot-pink Prada and bright-green Balenciaga socks she gifted him—items she admits she would never wear herself. Though she appreciates such exuberance on others, she prefers more subdued accessories and dismisses “fun socks” for her own wardrobe.
When it comes to fashion pet peeves, Bennett doesn’t hesitate. Flip-flops top the list, followed closely by ties worn over T-shirts, which she finds particularly distasteful. Her overarching philosophy of style is one of self-assurance and rejection of conformity. She believes in not wearing anything that doesn’t feel authentic. College, for her, was a time of dressing to fit trends and social expectations—a phase she now views as unnecessary. Her current approach champions personal choice and confidence over fleeting fashion movements.
Willa Bennett is more than the editor in chief of a major women’s magazine. She is a tastemaker reshaping how young people, especially women, approach fashion—drawing from the traditions of menswear to inspire new forms of self-expression. Through her vision and leadership, she challenges fashion norms while remaining deeply personal in her approach, embodying the idea that true style lies in authenticity and intention.
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