New York Fashion Week SS27: Best celebrity and street style looks so far


From Katie Holmes to Cynthia Erivo, these are the hottest looks spotted in the Big Apple this season


Clare Pennington
Clare PenningtonHello Fashion Editor
50 minutes ago
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As September dawns, it can only mean one thing - another fashion month is upon us. Kicking off proceedings is New York, an ever-flourishing hub of sleek, commercial design, with a jam-packed schedule featuring big hitters such as Calvin Klein, Diane von Furstenberg and Michael Kors.

Here at H! Fashion, we can't wait to see what trends will unfold as the month progresses (more rugby tops? Fingers crossed for lots of Y2K camo...) 

And of course, what's happening on the streets outside the shows can be just as exciting as the looks strutting down the runway. Previous seasons have seen the likes of Anne Hathaway in seriously sultry lace and Suki Waterhouse in a blue textured coat that we haven't stopped thinking about since. 

So let's drink in all the gorgeous looks spotted on the FROW and get ourselves in the mood for London Fashion Week, which kicks off on September 17.

Best NYFW SS27 street style looks:

Katie Holmes wears black pleated trousers and an off the shoulder top© Diana Zapata/BFA.com

Katie Holmes

Oh we love a fashion week Katie Holmes spot! The actress popped by the Cult Gaia presentation in a pair of perfectly pleated pants and an off-shoulder top.

Josh Heuston wears a black leather jacket and grey trousers© Diana Zapata/BFA.com

Josh Heuston

Off-Campus heartthrob Josh Heuston stopped by the Cult Gaia presentation wearing a classic black leather jacket and tailored trousers.

Anna Wintour wears a navy and cream striped dress© GC Images

Anna Wintour

Fashion heavyweight Anna Wintour stuck to her signature style in a navy and cream striped midi dress for the Ralph Lauren show. 

Viola Davis wears a grey knit top and leather midi skirt© GC Images

Viola Davis

Oscar-winning actress Viola Davis attended the Ralph Lauren show in a leather midi skirt, some buttery leather boots in brown and a sleeveless cable-knit top in charcoal grey.

Meghann Fahy wears a black leather coat and trousers© GC Images

Meghann Fahy

Meghann Fahy opted for a slick black leather coat and matching trousers for Ralph Lauren. A pair of heeled boots polished off her sleek attire to perfection.

Actress/singer Cynthia Erivo attends the Ralph Lauren fashion show during New York Fashion Week at Jack Shainman Gallery on September 09, 2026 i© GC Images

Cynthia Erivo

Wicked star Cynthia Erivo hit the streets looking suave in all-black. The actress opted for an on-trend military jacket, a pair of lengthy black trousers and a Y2K beret that topped off her utilitarian-chic aesthetic. 

Elizabeth Debicki wears a khaki coat, trousers, shirt and tie© GC Images

Elizabeth Debicki

Australian actress Elizabeth Debicki enjoyed a matchy-matchy moment at Ralph Lauren in a soft khaki ensemble complete with androdynous tie detailing. 

Eiza González wears leather trousers and matching shirt and waistcoat© GC Images

Eiza González

Eiza González stopped by the Ralph Lauren show looking thoroughly Western in leather trousers and a matching waistcoat layered over a pirate-esque shirt with sizeable balloon sleeves.