Tracee Ellis Ross, a true fashion icon, has once again set the style standard, this time mastering oversized transitional dressing. While in New York City for press promoting her Roku series ‘Solo Traveling,’ Ross stepped out in a look that perfectly captured the tricky fashion balance between summer and fall.
Nailing Transitional Dressing with Willy Chavarria
The entire ensemble was courtesy of designer Willy Chavarria, specifically Look 16 from his Spring/Summer 2026 collection. The oversized fit, combined with the crisp cream pinstripe button-down shirt tucked into high-waisted, wide-leg black trousers, created a powerful yet feminine silhouette. The trousers, pooling at the hem, added a touch of dramatic flair.
A black-and-gray striped tie introduced an androgynous edge, while a patent belt with a dangling key ring added a utilitarian touch. Completing the look were chunky black loafers and oversized square sunglasses, cementing the ensemble as a masterclass in playing with proportions and seasonal style.
Beauty and Hair That Match the Vibe
Ross’s hair and beauty choices were just as impactful as her outfit. The Pattern Beauty owner styled her natural curls with a deep side part, exuding confidence and effortless chic. Her makeup was natural and complementary, featuring a soft pink nude gloss that enhanced her features without overpowering the look.
Her appearance on ‘Jimmy Kimmel Live’ was part of her press tour for ‘Solo Traveling,’ which has officially been renewed for another season. This means more globe-trotting fashion moments from Ross are on the horizon, much to the delight of her fans.
Willy Chavarria: Fashion as a Platform
Willy Chavarria’s brand is known for its revolutionary fashion that makes bold statements, both stylistically and politically. His recent Paris Fashion Week show, which mirrored migrants in an El Salvador prison, highlighted fashion’s power as a platform for messaging. Much like Ross, Chavarria embodies bravery, beauty, and an unapologetic approach to life and art.
This synergy between Ross’s avant-garde wardrobe and Chavarria’s fearless design philosophy makes their collaboration a perfect fit. It’s an energy that has earned this look a permanent spot on our transitional dressing mood board.
What do you think of Tracee Ellis Ross’s oversized transitional look? Are you inspired to try this trend? Share your thoughts in the comments below!
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