The Most Unforgettable Moments From 35 Years of New York Fashion Week

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Photographed by Hunter Abrams

New York Fashion Week is upon us, taking a mostly digital format this season. For many of us, a virtual fashion show doesn’t hold a candle to the thrills of the real thing, and so we are looking back on 35 years of special NYFW moments. 

Jean-Michel Basquiat Walks the Comme Des Garçons Runway

Basquiat on the Comme des Garçons runway in 1987

Photo: Courtesy of Comme des Garçons

In the late 1980s, Comme des Garçons held several fashion shows in New York City, peppering its runway with locals alongside models. For the brand’s spring 1987 collection, Rei Kawakubo cast the consummate New Yorker, Jean-Michel Basquiat. He was, after all, already a fan: His favorite Comme des Garçons coat sold at auction in 2018 for $28,000

Marc Jacobs Puts Grunge on the Runway for Perry Ellis 

Perry Ellis spring 1993

Photo: Condé Nast Archive

Perry Ellis spring 1993

Photo: Condé Nast Archive

Perry Ellis spring 1993

Photo: Condé Nast Archive

Perry Ellis spring 1993

Photo: Condé Nast Archive

Marc Jacobs’s spring 1993 collection for Perry Ellis is the stuff of fashion lore. In translating the popular grunge look to the runways, Jacobs earned critical scorn, ultimately being dismissed from his position at Perry Ellis for the collection. His firing only made the collection more legendary—so much so that he reissued the pieces in 2019. 

Shocking Collections From Stephen Sprouse, Patrick Kelly, Todd Oldham, and Anna Sui

Anna Sui fall 1994

Photo: Courtesy of Anna Sui

Patrick Kelly spring 1989

Photo: Getty Images

Stephen Sprouse's 1987 show

Photo: Getty Images

Todd Oldham spring 1996

Photo: Getty Images

In the late ’80s and early ’90s, American fashion’s upstart designers ditched the seriousness of their power-dressing predecessors, favoring tongue-in-cheek fun and fantasy. Anna Sui dressed Christy Turlington, Naomi Campbell, and Linda Evangelista as puff-ball princesses. Patrick Kelly framed Yasmin Le Bon on the runway. Stephen Sprouse cut some of the most graphic and miniature dresses, while Todd Oldham made sure models like Veronica Webb were dressed scantily enough to rival his sparkling backdrop. 

Calvin Klein and Kate Moss Usher in the Era of the Waif

Calvin Klein spring 1994

Photo: Condé Nast Archive

Calvin Klein’s spring 1994 collection ranks on as one of the ultimate ’90s shows not just for its all-star model cast but also its complete rejection of bombshell style. By the mid-’90s, Klein and Kate Moss would come to symbolize the waif look: relaxed, sensual, and a little aloof. 

Isaac Mizrahi Gets Unzipped

A still from Unzipped

Photo: Courtesy of Miramax

A still from Unzipped

Photo: Courtesy of Miramax

It’s the ultimate fashion dream: A runway show at New York Fashion Week. But as Unzipped proved to a generation of fashion-obsessed fans, there is a lot of behind-the-scenes work—and drama—that makes Fashion Week possible. The documentary of Isaac Mizrahi’s spring 1994 collection still inspires to this day. 

Helmut Lang Moves NYFW Up by Three Weeks

Helmut Lang spring 1999

Photo: Courtesy of hl-art

Helmut Lang spring 1999

Photo: Courtesy of hl-art

Helmut Lang spring 1999

Photo: Courtesy of hl-art

Helmut Lang spring 1999

Photo: Courtesy of hl-art

Helmut Lang might be best remembered as the most utilitarian minimalist—and maybe the kinkiest too—but he did a lot for the fashion system. For fall 1998, he became the first designer to go digital by sending out images of his collection on CD-ROMs. One season later, spring 1999, he moved his show forward by three weeks, to take place before London, Milan, and Paris Fashion Weeks. NYFW has occupied the first spot on the four-city major tour since. 

Alexander McQueen Lands Stateside

Alexander McQueen spring 2000

Photo: Condé Nast Archive

Lee McQueen reveals American flag boxers during his bow

Photo: Condé Nast Archive

Many will remember Lee Alexander McQueen’s antics at the end of his spring 2000 show, revealing American-flag boxer shorts, but his spring 2000 lineup shouldn’t be overshadowed. Shown on the West Side of Manhattan, it was one of his most sensual collections of his early career.

Miguel Adrover Upcycles While Prodding the System

Miguel Adrover fall 2000

Photo: JB Villareal / Shootdigital for Style.com

“It was my city; it was where people accepted me, where I could raise my voice and all that stuff,” said Spanish designer Miguel Adrover of New York. His second collection, for fall 2000, was a level of provocative NYFW might not have been ready for. He repurposed Burberry trenches and Louis Vuitton bags on the runway. The show was lauded but didn’t have a fairy-tale ending: He was sued by Burberry. 

Rick Owens Stages His First Show Ever

Rick Owens fall 2002

Photo: Style.com

Rick Owens fall 2002

Photo: Style.com

Rick Owens fall 2002

Photo: Style.com

Before he was the god-king of European fashion, Rick Owens was making “Scotch-tape Vionnet” dresses in California. After a visit from Vogue and Style.com editors, Owens was plucked from Los Angeles and put on the runway in New York. The rest is history.

Imitation of Christ Dies, Thrives, and Criticizes

Imitation of Christ spring 2001

Photo: JB Villareal / Shoot Digital for Style.com

Imitation of Christ fall 2001

Photo: JB Villareal / Shoot Digital

Imitation of Christ spring 2002

Evan Agostini

Imitation of Christ burst on to the fashion scene with upcycled vintage garments and performative fashion shows that challenged the traditional white-box runway. The brand’s spring 2001 show was a funeral that founders Tara Subkoff and Matt Damhave followed up with a paparazzi-ready red carpet show for fall 2001. The duo’s spring 2002 show might be their most unorthodox yet: Models sat in rows along a runway and took notes, photos, and phone calls about the outfits guests wore while they walked in. 

NYFW Gets Celeb-ified

Sweetface fall 2005

Marcio Madeira

Sean John fall 2008

Marcio Madeira

L.A.M.B. spring 2006

Marcio Madeira

Before there was Savage x Fenty or Tommy x Gigi, there was the late-aughts celebrity-fashion boom. Jennifer Lopez launched her Sweetface collection at NYFW in 2006, while Puff Daddy brought his Sean John collection to the catwalk by 2008, and Gwen Stefani had intermittent stints on the catwalk with her L.A.M.B. line throughout the aughts and teens. 

The Kors and Kass Era

Michael Kors spring 2004

Photo: Getty Images

Michael Kors fall 2004

Randy Brooke

Michael Kors fall 2008

Karl Prouse/Catwalking

Michael Kors spring 2008

Chris Moore/Catwalking

Michael Kors has been an NYFW staple for decades, but one could argue that his 2004–2014 era of opening shows with a male-female duo was particularly unforgettable. In that decade, Carmen Kass had the honor of opening the most Kors shows—six in total—defining the look of the late aughts and early teens with her bronzy complexion, catty strut, and aviator sunglasses. 

Kim Kardashian and Paris Hilton Hit the Runway for Heatherette 

Paris Hilton on the Heatherette spring 2007 runway

Photo: Getty Images

Kim Kardashian West on the Heatherette spring 2008 runway

Photo: Getty Images

Richie Rich and Traver Rains’s brand Heatherette was famous for gumdrop dresses, over-the-top runways, and celebrities on their catwalk. Paris Hilton appeared on several of them from 2004 to 2008, while her BFF and onetime assistant Kim Kardashian West took a turn for the duo for spring 2008. 

Betsey Johnson Can’t Stop Cartwheeling

Johnson cartwheels at the end of a show in 2008

STAN HONDA

Few things are certain: death, taxes, and Betsey Johnson cartwheeling down her NYFW runway. She’s done the acrobatic trick without fail at every one of her shows.

Marc Jacobs Raises the Bar on Set Design

Marc Jacobs spring 2006

Randy Brooke

Marc Jacobs fall 2013

Catwalking

Marc Jacobs spring 2007

Catwalking

Marc Jacobs fall 2012

Chris Moore/Catwalking

New York Fashion Week is not the same without Marc Jacobs’s fantastical sets—and the clothes to match their brilliance. Starting in 2006 when he booked the Penn State Nittany Lions marching band, Jacobs and set designer Stefan Beckman have conceived sunsets, pink houses, candy landscapes, and paper castles to complement Jacobs’s emotive clothing. 

Opening Ceremony Rolls into NYFW

Opening Ceremony's first runway show in 2013

Mark Von Holden

While Opening Ceremony, the store, was founded in 2002, the brand never held a fashion show for its in-house collection until 2013. In OC fashion, the show was delightfully bonkers. Each model rode onto the runway in a sports car—BMWs, Ferraris, and Porsches were in the mix—while an audience that included Justin Bieber and Rihanna looked on. 

Miley Cyrus and Jeremy Scott Are BFFs

Jeremy Scott spring 2015

Yannis Vlamos / Indigitalimages.com

One year after Miley Cyrus’s now-legendary VMAs performance, she arrived at New York Fashion Week with a jewelry collaboration with Jeremy Scott. Trying to elbow your way into the Milk Studio show space was hard enough, and once inside, you were treated to childlike gems by Cyrus and a cheery bow from the musician and designer. 

Givenchy Salutes New York City

Givenchy spring 2016

Photo: Alessandro Garofalo / Indigitalimages.com

Riccardo Tisci honored New York City with a solemnly beautiful runway show held on Pier 26 on the Hudson River on September 11, 2015. Produced in collaboration with Marina Abramovic, the show featured performance artists suspended on high platforms, though what we really remember are the clothes. With an end of his term at Givenchy in view, Tisci recreated his greatest hits on the runway, casting all his favorite models to show them off while Nicki Minaj and more A-listers looked on. 

Hood by Air Rules NYFW

Hood by Air fall 2014

Yannis Vlamos / Indigitalimages.com

Hood by Air fall 2015

Stefano Masse / Indigitalimages.com

Hirakish at the Hood by Air fall 2016 show

Photo: Marcus Tondo / Indigital.tv

Wolfgang Tillmans walks the Hood by Air fall 2017 runway

Photo: Yannis Vlamos / Indigital.tv

The HBA era at NYFW might have been brief, but it was impactful. Shayne Oliver’s brand of performance-turned-show only strengthened the impact of his deconstructed ready-to-wear. The good news is HBA is planning a comeback in 2021. 

Thom Browne Keeps NYFW Alive

Thom Browne fall 2015

Fernando Leon

It’s only fashion—not heart surgery! Hmm, not for Thom Browne. The designer’s fall 2015 show was set in an operating theater of sorts, providing a haunting setting to mirror his gothic designs. 

Yeezy Takes New York

Yeezy at Madison Square Garden

Photo: Yannis Vlamos / Indigital.tv

Yeezy on Roosevelt Island

Photo: Jackie Nickerson

Love him or hate him, you can’t argue with the impact Kanye West’s Yeezy shows had during their run in New York. On an unparalleled scale, the shows blended fashion, art, music, celebrity, and theater.

Tommy Hilfiger Rethinks the Celebrity Collab

The Tommy x Gigi runway in 2016

Paul Morigi

Tommy x Zendaya in 2020

ANGELA WEISS

While celebrities can struggle to set up their own fashion brands, a collaboration offers an easy entrée into the world of fashion. Tommy Hilfiger shared his catwalks with Gigi Hadid and Zendaya. Both partnerships resulted in spectacular runway presentations and a renewed energy for Hilfiger’s brand. 

Raf Simons Goes Pop at Calvin Klein

Calvin Klein 205W39NYC fall 2018

Photo: Alessandro Garofalo / Indigital.tv

The snow- and salt-covered sidewalks were no match for what guests encountered at Raf Simons’s fall 2018 Calvin Klein show: popcorn. The entire former Stock Exchange building in Lower Manhattan was covered in about six inches of popcorn, serving as a crunchy backdrop to Simons’s prairie gothic collection. 

Ralph Celebrates the Big 5-0 in Central Park

Photographed by Corey Tenold
Photographed by Corey Tenold

Few fashion shows come with a dress code, but Ralph Lauren’s 50th-anniversary celebration in Central Park was strictly black tie. The evening affair saw a front row that included Hillary Rodham Clinton and Oprah Winfrey, while models of all generations hit the runway in the best of Ralph’s oeuvre. 

Pyer Moss Takes Fashion in New Directions

Pyer Moss spring 2019

ANGELA WEISS

Kerby Jean-Raymond’s pair of fashion shows for spring 2019 and spring 2020 were undoubtedly the most talked-about American shows of those years. Leaving Manhattan for Weeksville, Brooklyn (one of the first communities of Black people freed from enslavement) and King’s Theater in Brooklyn, Jean-Raymond presented a pair of collections that celebrated Black creativity and contributions to American culture. 

Pyer Moss spring 2020

Photographed by Corey Tenold

Three’s a Party for Vaquera, CDLM, and Section 8

Vaquera spring 2020

Photo: Filippo Fior / Gorunway.com

CDLM spring 2020

Photo: Filippo Fior / Gorunway.com

Section 8 spring 2020

Photo: Filippo Fior / Gorunway.com

Amidst a bulked-up and chaotic NYFW schedule, three young brands found a solution: a group show. Held in a theater in Midtown, the Vaquera, CDLM, and Section 8 joint show offered a new path forward for young talents looking to ensure that press and retailers were able to attend their shows. Why haven’t we seen this sort of collaboration since? 

Telfar Takes Over Irving Plaza

Telfar fall 2019

Photographed by Corey Tenold

Telfar fall 2019

Photographed by Corey Tenold

After a concert at Spring Studios, Telfar Clemens amplified his musical message for fall 2019, taking over Irving Plaza for a rock star fashion show. Packed to the rafters—and with a two-hour wait to enter—the show cemented Clemens’s status as a fashion disrupter. 

Tomo Koizumi Ruffles Onto the Scene

Gwendoline Christie at Tomo Koizumi's show in 2019

Photographed by Hunter Abrams

Before February 2019, Tomo Koizumi was a virtual unknown in Western fashion. But after being spotted by Katie Grand on Instagram, Koizumi was offered a NYFW show at Marc Jacobs’s Madison Avenue store. Gwendoline Christie, Emily Ratajkowski, Bella Hadid, and Rowan Blanchard walked in Koizumi’s frilled confections. 

Rihanna Upstages That Other Lingerie Fashion Show

Joan Smalls at the Savage X Fenty show

Craig Barritt

Rihanna’s first Savage x Fenty show brought fashion to a Brooklyn greenhouse. For her second, she took us to Barclay’s Stadium for a to-be-televised special that celebrated all body types and all creative outlets. Airing on Amazon Prime weeks later, the Savage x Fenty runway show quickly became America’s best televised fashion show. 

Eckhaus Latta Walks It Off

Eckhaus Latta spring 2021

Photographed by Corey Tenold

Six months into the COVID-19 pandemic, fashion was tip-toeing through an abridged season. Eckhaus Latta offered a New York solution to no more fashion shows: A guerrilla show held on a running path in Lower Manhattan. Models wore masks, and guests numbered in the single digits.