Tracee Ellis Ross stepped out on the streets of Los Angeles in an oversized menswear-inspired ensemble that has us all searching the web for striped neckties. Her predominantly Willy Chavarria look consisted of high-rise wide leg pants with pleats, a tucked oversized pinstriped white button down shirt, a black and gray diagonally striped necktie, and shiny black loafers. Other accessories included a classic black belt, a belt loop keychain, and oversized black sunglasses.
Getty ImagesRoss has been working with celebrity stylist Karla Welch for years, together cultivating so many intriguing red carpet moments, notably the 2017 American Music Awards which involved several outfit changes and an iconic tribute to Ross’ mother Diana Ross. The two collaborate on looks of varying aesthetics and eras, always aiming to create something worth talking about.
Ross’ look had me naturally thinking about the significance of women in menswear throughout history, and about what exactly it means for women to embrace baggier fits. The Jazz Age introduced flapper dress with drop waists and looser fits, finally moving away from corsets and the concept that a woman’s most valuable asset is her shape. Traditionally masculine fashion grew in popularity when women gained more status in the corporate world in the ‘80s. ‘90s hiphop and grunge, as well as fashion moments from iconic tv shows like Beverly Hills 90210, really affirmed menswear on women as a trend.
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With stars like Billie Eilish embracing a baggy silhouette regularly, Hailey Bieber occasionally whipping out a crisp oversized Saint Laurent suit, and Ayo Edebiri paying tribute to an iconic 1999 Julia Roberts look in a Loewe suit at the 2025 Golden Globes, and cosigned by luxury brands such as The Row and Bottega Veneta as shown in their Spring/Summer 2025 collections, the trend isn’t going anywhere. Is it to make a statement or to just opt for comfort? Probably both. It’s a win-win.
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I think of masculine oversized clothing on women as a protest—it was then and it, unfortunately, still is now—and Tracee Ellis Ross is the latest to take a stand.
