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


From Katie Holmes to Anne Hathaway and Emily Ratajkowski, these are the hottest looks spotted in the Big Apple this season


Emily Ratajkowski at the Dior and A24 Celebrate the Cherry Lane Theatre on September 10, 2026 in New York, New York© WWD via Getty Images
Hello Fashion
Clare PenningtonHello Fashion Editor
Tania LeslauFashion Features Editor
Updated: September 15, 2026
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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 Tory Burch, 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:

Natalia Dyer attends the Carolina Herrera fashion show during New York Fashion Week:© GC Images

Natalia Dyer

Stranger Things star Natalia Dyer stepped out to attend the Carolina Herrera show, dressed to the nines in a strapless gown printed with sprawling blooms.

 Emily Ratajkowski attends the Calvin Klein Spring /Summer 2027 Fashion Show during New York Fashion Week© GC Images

Emily Ratajkowski

A mainstay on the NYFW scene, Emily Ratajkowski attended the Calvin Klein SS27 show in all-white. The model wore a sleeveless white turtelneck teamed with matching low-rise trousers.

Lila Moss attends Calvin Klein Spring /Summer 2027 Fashion Show during New York Fashion Week© GC Images

Lila Moss

Lila Moss delivered a lesson in streamlined 90s style as she posed for snaps outside the Calvin Klein show, styling out a pinstriped midi skirt, heels and a checkered shirt.

Teyana Taylor attends the Calvin Klein Spring /Summer 2027 Fashion Show© GC Images

Teyana Taylor

Teyana Taylor looked radiant in a strawberry red trench coat paired with a pillbox hat and snow white trousers at the Calvin Klein SS27 display.

Tate McRae attends the Calvin Klein Spring /Summer 2027 Fashion Show© GC Images

Tate McRae

Tate McRae looked dreamy in double denim as she served up 90s nostalgia outside the Calvin Klein SS27 show.

Actress Sadie Sink attends the Calvin Klein RTW Spring /Summer 2027 Fashion Show© GC Images

Sadie Sink

Championing the brand's signature office-inspired tailoring, Stranger Things star Sadie Sink attended the Calvin Klein SS27 show looking polished in a pinstriped shirt-trouser set.

 Iris Law attends Khaite Fashion Show in Brooklyn© GC Images

Iris Law

Model and actress Iris Law tapped into the military jacket trend with a sleek black option as she graced the scene outside the Khaite show in Brooklyn.

Elsa Hosk attends Khaite Fashion Show in Brooklyn© GC Images

Elsa Hosk

Victoria's Secret model Elsa Hosk re-established her sartorial credentials as she stepped out for the Khaite show in dark-wash denim and patent black leather layers.

Actress Pamela Anderson attends the Khaite Spring /Summer 2027 fashion show at Brooklyn Navy Yard © GC Images

Pamela Anderson

Actress Pamela Anderson attended the Khaite show wearing a structured, longline dress in ebony black featuring button-down detailing and lengthy sleeves.

Nara Smith attends the Khaite Spring /Summer 2027 fashion show at Brooklyn Navy Yard© GC Images

Nara Smith

Nara Smith backed one of 2026's stand-out trends, the military jacket, which she styled with leather trousers and heels for the Khaite show in Brooklyn.

alexa Chung attends the Khaite Spring /Summer 2027 fashion show © GC Images

Alexa Chung

British model and muse pioneered sweetheart style in a black babydoll at the Khaite SS27 show.

Gigi Hadid is seen walking the runway at the Tommy Hilfiger fashion show during New York Fashion Week© GC Images

Gigi Hadid

Americana muse Gigi Hadid was spotted outside the Tommy Hilfiger show in a pair of bright strawberry red trousers and a denim bucket hat.

Yasmin Wijnaldum attends the Tommy Hilfiger fashion show during New York Fashion Week: © GC Images

Yasmin Wijnaldum

Model Yasmin Wijnaldum coolly graced the scene at the Tommy Hilfiger SS27 show sporting some low-waisted blue jeans and a graphic ringer tee.

Camila Cabello is seen at the Tommy Hilfiger fashion show during New York Fashion Week at The Plaza Hotel, © GC Images

Camila Cabello

Camila Cabello was another familiar face seen at the Tommy Hilfiger fashion show. The singer sported a preppy red mini skirt and knit combo, finished with a classic white tee and a black clutch.

Romeo Beckham attends the Tommy Hilfiger fashion show during New York Fashion Week© GC Images

Romeo Beckham

Romeo Beckham returned to the runway for Tommy Hilfiger's SS27 offering, later hitting the streets of NYC in a checked shirt and Bermuda short ensemble.

Madeline Petsch is seen at the Tommy Hilfiger fashion show during New York Fashion Week © GC Images

Madeline Petsch

Actress and vegan activist Madeline Petsch made a case for nostalgic striped polo shirts outside the Tommy Hilfiger fashion show. Very Gossip Girl, don't you think?

 Kate Moss attends the Tommy Hilfiger fashion show during New York Fashion Week:© GC Images

Kate Moss

Supermodel and British icon Kate Moss stepped out in jeans and a crisp poplin shirt to attend the Tommy Hilfiger show in the Big Apple.

Winnie Harlow attends the Tommy Hilfiger fashion show during New York Fashion Week© GC Images

Winnie Harlow

US model Winnie Harlow posed up a storm in a preppy rugby shirt and patchwork jeans outside the Tommy Hilfiger fashion show.

Emily Ratajkowski at the Dior and A24 Celebrate the Cherry Lane Theatre on September 10, 2026 in New York, New York© WWD via Getty Images

Emily Ratajkowski

Following her appearance on the Tory Burch runway, Emily Ratajkowski attended the Dior and A24 Celebrate the Cherry Lane Theatre bash in a slinky petrol blue cowl-neck top and low-slung trousers.

Amanda Seyfried  attends the Tory Burch Spring Summer 2026 show during New York Fashion Week © Getty Images for Tory Burch

Amanda Seyfried

Amanda Seyfried dropped the hottest new colour combo of the season - chartreuse and caramel, as she took her place on the Tory Burch FROW.

Olivia Jade Giannulli attends the Tory Burch Fashion Show during New York Fashion Week© GC Images

Olivia Jade Giannulli

Olivia Jade Giannulli delivered a masterclass in colour theory as she attended the Tory Burch show in a gleaming gold and baby blue ensemble. 

Cindy Crawford attends NET-A-PORTER event at the Straker's in SoHo during NYFW © GC Images

Cindy Crawford

90s supermodel Cindy Crawford attended the NET-A-PORTER bash in an all-black outfit featuring a longline leather skirt and matching jacket.

Serena Williams attends NET-A-PORTER event at the Straker's© GC Images

Serena Williams

Tennis champ Serena Williams delivered a vibrant violet mini dress moment as she attended the NET-A-PORTER event at the Straker's.

Anne Hathaway attends the Moncler Fifth Avenue Flagship Store Opening at Moncler Fifth Avenue Flagship on September 10, 2026 in New York City. © Patrick McMullan via Getty Image

Anne Hathaway

Anne Hathaway displayed her blossoming baby bump in dreamy double denim as she graced the scene at the Moncler Fifth Avenue Flagship Store Opening.

 Adriana Lima attends the Moncler Fifth Avenue Flagship Store Opening at Moncler Fifth Avenue Flagship on September 10, 2026 in New York City. © Patrick McMullan via Getty Image

Adriana Lima

Supermodel Adriana Lima was a cream dream at the Moncler Fifth Avenue Flagship Store Opening, sporting white jeans, a white pullover and a textured coat.

Paris Hilton attends the Kering Foundation's Fifth Annual Caring For Women Dinner © GC Images

Paris Hilton

Also in attendance at the star-studded bash was none other than Y2K queen Paris Hilton, who stole the show in a gold, skin-tight gown featuring a longline cut and raised neckline.

Rita Ora attends the Kering Foundation's Fifth Annual Caring For Women Dinner © GC Images

Rita Ora

Never one to miss out on a good time, Rita Ora attended the Kering bash in a sleek black gown complete with a resplendent finish.

Actor Colman Domingo attends the Kering Foundation's Fifth Annual Caring For Women Dinner at The Pool on September 10,© GC Images

Colman Domingo

Colman Domingo cemented his fashion credentials in a beautifully embroidered suit jacket at the Kering Foundation's Fifth Annual Caring For Women Dinner.

Camila Morrone attends the Kering Foundation's Fifth Annual Caring For Women Dinner at The Pool© Getty Images for Kering Foundati

Camila Morrone

Argentinian actress and Chanel muse Camila Morrone dazzled in a gold snakeprint bodycon gown during the Kering Foundation's Fifth Annual Caring For Women Dinner.

 Jessica Chastain attends Moncler Fifth Avenue Flagship Opening at 767 Fifth Avenue © Getty Images

Jessica Chastain

Zero Dark Thirty star Jessica Chastain made a case for the timeless LBD at the Moncler Fifth Avenue Flagship Opening at 767 Fifth Avenue.

Princess Olympia attends the Moncler Flagship Opening dinner at Gotham Hall © GC Images

Princess Olympia of Greece

Princess Olympia of Greece took the stage in a playful tailored romper with belted detailing as she attended the Moncler Flagship Opening dinner.

Alex Consani attends the 2026 Kering Foundation Caring For Women Dinner© WireImage

Alex Consani

Top model made an entrance at the 2026 Kering Foundation Caring For Women Dinner in a striking electric blue gown with a heavily textured finish.

Julia Roberts at the Moncler Fifth Avenue Opening Cocktail Party & Dinner held at the Moncler Fifth Avenue Flagship store © WWD via Getty Images

Julia Roberts

Hollywood heavyweight Julia Roberts enjoyed a monochrome moment at the Moncler Fifth Avenue Opening Cocktail Party & Dinner held at the Moncler Fifth Avenue Flagship store.

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.