The Comedy Kings of New York City Street Style

The Big Apple has long been home to some of the world’s most fashionable people. Every day, New Yorkers take to the city streets showing off their Vogue-esque street style and late-night looks. In a city fueled by diversity, art and creative expression, style naturally rises to the forefront of culture. When we think about creativity through a style lens, we often picture actors, dancers or even painters. Rarely, however, do we think of the group quietly leading the charge in edgy, innovative New York City street style: comedians.

The boys of stand-up comedy have been subtly, yet stylishly, influencing fashion trends across social media for some time now. In a career built on self-expression and often self-deprecation, these comedians aren’t afraid to let their fashion freak flags fly, embracing bright colors, mixed textures and patterns and gender-neutral silhouettes. While many men are embracing the progressive styles of the 2020s, a few comedians have been leading the New York City pack when it comes to dressing to impress.

MGG: Matthew Gray Gubler

CBS’ Dr. Spencer Reid claimed the esteemed title of New Yorker back in the early 2000s, gracing the streets of SoHo with boundary-breaking outfits and vibrant color. The “Criminal Minds” actor’s bold fashion frequently lands him in some of New York’s hottest style publications and social media accounts, including “The People Gallery” and “Watching New York.”

Matthew Gray Gubler’s whimsical stylistic flair makes him hard to miss as he glides through the city, often in a floor-length peacoat or cross-buttoned blazer. Gubler famously draws much of his style inspiration from Japanese culture and is frequently pictured wearing pieces from his extensive collection of traditional silk kimonos.

He is also a fan of layers — and lots of them. Even during New York’s sweltering summer months, Gubler can often be seen in nothing less than a vintage tee, an oversized cable-knit sweater and a structured blazer, tying together his signature business-modish outfits.

Gubler’s comedic playfulness shines through each and every one of his carefully curated outfits, making him a pioneer within New York City’s fashion scene. 

Connor Wood: aka Fibula

The podcast prince of comedy recently made the move from L.A. to New York back in March of 2025 and has already solidified his spot within New York City street styles’ leading men. The comedian, best known as the co-host of “Brooke and Connor Make a Podcast” has already influenced NYC fashion culture through his playful yet manicured attire. The only time Wood is seen without one of his signature trucker hats is when he graces a red carpet in pristinely tailored tux. 

Like Gubler — a frequent topic of conversation on Wood’s podcast-turned-friendship — Wood’s closet is filled with every color on the wheel. From baby pink blazers to forest green cable-knit sweaters, he has mastered the comfortable yet cool style of New York City’s West Village.

HenryHenryHenryHenryHenryHenry

The self-proclaimed king of Tote Bags, Henry Smith, better known as HenryHenryHenry to his 100,000 Instagram followers, is the fashion world’s newest bi-coastal superstar. HenryHenryHenry received an official fashion stamp of approval in December when he was followed on Instagram by New York street style icon Sarah Jessica Parker, aka the ever iconic Miss Carrie Bradshaw.

Raised in San Diego, CA, HenryHenryHenry brings the California-cation to the cobbled streets of SoHo. HenryHenryHenry’s minimalist style and classic silhouettes encapsulate the timeless fashion of the Big Apple. Choosing mostly neutral color palettes, HenryHenryHenry’s style carries him off the New York City streets into any space he chooses, whether that’s a red carpet or a local West Village dive bar. 

Who do you think is the comedy king of NYC? Let us know your thoughts @VALLEYMag on X!

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