7 of Amanda Lepore’s most iconic outfits

The legendary trans model, singer, fashion muse, and eternal New York Club Kid shows that being yourself is the most stylish look of all.

Growing up in suburban New Jersey during the 1970s and 80s, while often being bullied at school for being different, Amanda Lepore completed her sex reassignment surgery at the age of 19. “I would never let anything get in my way… I just did my thing,” she recalled in Gay Times magazine, many years later. By the early 90s, she had moved to New York - swiftly embraced by the city’s most out-there nightlife and fashion scenes. Freaking out mainstream America with occasional appearances on daytime TV – notably on Richard Bey’s show in 1991 with a young RuPaul – Amanda, Ru, Jeremy Scott and their group of dressed-to-kill NY Club Kids rose to fame and notoriety during the ensuing decade. 
Via various surgical enhancements, her incredible appearance has gradually morphed into a more extreme version of a high-glamour prototype. Think: Marilyn Monroe meets Jessica Rabbit. Sometimes, however, Amanda walks out in very little, or literally nothing in public; proudly showing off a body akin to a work of art.

6 PHOTOS

1. Such dedication to style and image (Amanda always does her own make-up, btw), alongside a gentle and good-humored nature, has made Amanda both a collaborator and source of inspiration to countless fashion designers, pop stars, and other creatives, along the way. Her sartorial chums of past and present include Donatella Versace, Manfred Thierry Mugler, Demna, and Casey Cadwallader, among others. She has also modeled for Armani Jeans, Mac Cosmetics, and Jean Paul Gaultier, and is regularly photographed by superstar snappers Stephen Klein and David LaChapelle. Lady Gaga, Pamela Anderson, and Miley Cyrus have all expressed their adoration of her; Miley once even declared, “I hate everyone but Amanda Lepore!”   

Proving she is not just a Warholian embodiment of famous-for-being-famous, hard-grafting Amanda has not only appeared in the music videos of other artists, such as Elton John and Grace Jones but also successfully recorded and released tracks of her own, such as underrated 2005 banger “My hair looks fierce”. Spending the past 20-plus years gracing or performing at just about every notable niterie in Manhattan and beyond, she also found time to write a best-selling autobiography in 2017, entitled Doll Parts, and launch an eponymous lipstick brand in 2020. 
That is all to say, Amanda is such a fabulous one-off. In fact, she is routinely flown around the world simply to turn up and hang out at the latest, hottest club. Why? Because when Miss Lepore arrives everyone knows the party has started! Here, we pay tribute to her iconic legacy with a handful of Amanda’s most iconic outfits.    

At a movie premiere with David LaChapelle, 1990
Even in her early 20s, Amanda was already pioneering a super-modern, multi-hyphenate approach to paying rent, though her eclectic employment and side hustles must have left little time to catch up on beauty sleep. By day, Amanda was a cosmetics sales assistant in the kooky East Village fashion boutique owned by Sex and the City stylist, Patricia Fields. Eventually closing down in 2015, the spot was a regular hangout for NYC’s wildest dressed Club Kids, from drag queens and celeb shoppers including Miley Cyrus, Lady Gaga, and Missy Elliot. During her time at the store, though, she was less than customer-focused, stating in 2015, “I was around all those mirrors. I would just look at myself all day.” Understandable tbh! Come nightfall, though, she’d show off her color-coordination skills in iconic looks as she danced the night away working at legendary clubs such as Limelight in New York City, or making friends on the Club Kid scene and with the likes of David LaChapelle.

In a Mac Cosmetics and Heatherette advert, 2000
Amanda is known for her trademark luscious lips, always sheened with a generous application of vividly-hued lipstick. So, her designer friends Richie Rich and Traver Rains – founders of cult, early-00s, NY label Heatherette, whose fans included Naomi Campbell, Paris Hilton, and Kim Kardashian – celebrated her pouting pride and glory, when they launched a collab with MAC Cosmetics, in 2000. The accompanying promotional video, shot by David LaChapelle, commences in a relatively straightforward fashion, as Amanda begins expertly coating her lips with bright pink lipstick to a soundtrack of opera music. Gradually, however, her make-up ‘technique’ becomes decidedly more and more bonkers...      

2. At a movie premiere, in 2003

Feline pretty in Hello Kitty! This cuddly-looking dress was a key piece from a 2003 collab between the cutesy Japanese brand Hello Kitty and Heatherette. Many years later, in 2019, the giddy creation would be included in the New York Metropolitan Museum of Art’s hugely successful Camp: Notes on Fashion exhibition. Back in 2003, though, its debut took place at Heatherette’s giddy runway show staged in Los Angeles starring both Amanda and Paris Hilton as models. In the aftermath of the collection having been unveiled, Amanda rocked up to a movie premiere wearing the show-stopping number. The result? Her look got loads of attention and, by 2010, Hello Kitty was reportedly worth $5 billion per year. Amanda’s impact? Maybe.

3. Backstage at the Kaimin AW18 show, 2018

Typically, Amanda takes about two hours to get ready and dressed up for a night out, in her tiny room at Hotel 17, where she’s lived since the mid-90s. That is, at least when she’s not dispensing with clothes altogether, enjoying the empowerment and freedom of full-on nudity while hitting the clubs. She’s also famously been photographed naked by David LaChapelle, who, according to Amanda, thinks she looks better without clothes on. Here, though, she graces the runway of NY designer Kaimin in a see-through dress from his AW18 collection. Even the usually outraged-about-everything UK tabloid The Daily Mail couldn’t help but bashfully marvel at Amanda’s ‘sheer’ nerve. The story commented that her outfit “did nothing to mask the star's gravity-defying chest or any of her other intimate parts” while noting approvingly that Amanda, “sauntered down the runway... exuding maximum sass.” She certainly did.

4. At the Moschino Pre-Fall 2020 show, 2019

Amanda and her famous designer mate Jeremy Scott – the long-term Creative Director of Moschino until earlier this year – both go way back. Their paths first crossed in early-90s NYC, when she was already horning herself into becoming a Big Apple sensation and he was one of the most promising fashion design students at The Pratt Institute. So, when Jeremy decided to stage Moschino’s Pre-Fall 2020 collection inside subway train carriages housed in the New York Transit Museum in downtown Brooklyn, of course, Amanda was a guest of honor, along with Winnie Harlow, Kim Petras, and Julia Fox. Needless to say, the starlet of style didn’t dress down for her reunion with Jeremy, serving retina-poking pink vibes in a clingy dress with matching full-length evening gloves. 

During NYC Pride, 2021
Amanda never shies away from her loyalty to the LGBTQ+ community (or shies away from anything at all, really!), so when it comes to the annual Pride event in NYC she is not just out and proud, she’s scantily clad and fierce. This particularly revealing Pride look from 2021 – comprising of the tiniest slivers of leopard print fabric, teamed with oversized sunnies, and peroxide tresses teased perfectly into place by her hairstylist pal Lorenzo Diaz – demonstrates that true fashion icons pay no heed to dreary considerations such as keeping warm. Amanda doesn’t need a coat, anyway, as her non-stop dancing ensures she’s a goosebump-free zone.    

5. At the Balenciaga Resort 2023 show, 2022

Another year, another season... another fashion show for Amanda to attend! This time around, she was there to see Balenciaga’s Resort 2023 collection, shown within the New York Stock Exchange building in May 2022. Other celeb invitees turning the heads of passers-by as they arrived included Megan Thee Stallion, Marc Jacobs, and Frank Ocean. Bumping into Anna Wintour outside, the scene created an unparalleled high fashion moment! Amanda was mega-glammed-up in a tight-af dress created by the couturier and corsetier, Garo Sparo (which she had further customized herself by adding some jewel detailing). Accessories included earrings made by the costume jewelry designer Robert Sorrell, gloves courtesy of the burlesque dancer-turned-designer, Dita Von Teese, and teeteringly-high heels from Louboutin. FROW queen and all-around fashion legend Anna was, for once, left well and truly in the shade!