The unlikely return of the Y2K tiny vest

Anyone who went through adolescence in 2006 remembers that in September of that year, the album FutureSex/LoveSounds by Justin Timberlake was released. From September of that year until around March 2008, when 4 Minutes was released, Timberlake and his look captured the imagination of a generation of teenagers with an iron grip: three-piece suits; semi-formal combos of shirts and sneakers; ties, fedoras, and especially vests. The stylist responsible for Timberlake's transformation was, at the time, former Elle director Joe Zee, responsible for the looks of Johnny Depp and Lenny Kravitz, who at the time were also adopting a semi-formal, vaguely Al Capone-inspired look. "The ties and tight suits come from Dior Homme, Saint Laurent - which Timberlake often wears - and Gucci, so we mixed jeans or skinny pants and added vintage vests, fedoras, and all these things. In the end, he's a stylish guy who knows how to give his personal touch," Zee once told the LA Times. But every celebrity is remembered for something, and the suit vest was the accessory that stayed etched in everyone's minds – along with the fedora and the loosened tie worn like a necklace. As noted by Dee, vests were not always part of the "branded" looks, and their presence was both a brief infatuation the entertainment industry had with the '20s/'30s (it was also the era of Christina Aguilera's Back to Basics and Jay-Z's American Gangster, as well as movies like Chicago and The Aviator, for example) and an attempt at an unconscious mediation between '90s hip-hop style and the eclectic Indie Sleaze wardrobe of the time.

Justin Timberlake

Kate Moss

Kate Moss

Usher

Andrè 3000

Kate Hudson

Paris Hilton

Lindsay Lohan

Kim Kardashian

Fergie

Ashley Tisdale

Usher

LeBron James

Johnny Depp

Ryan Reynolds

Lindsay Lohan

Zac Efron

Johnny Depp

LeBron James

LeBron James

Chad Michael Murray

Jay Z

Selena Gomez

Today, especially for men who grew up in those years, the vest phase is an inevitable episode of their adolescence and is considered quite cringe – unlike in womenswear where the vest remained an accessory with a definite rock appeal both then and now. Be that as it may, in the last two fashion seasons, the vest seems to have returned: if not in its three-piece version as seen on the runways of Armani and Tom Ford, certainly in a new version more directly inspired by the unforgettable style exemplified by Kate Moss in 2005, when she appeared at the Glastonbury Festival with Pete Doherty wearing micro-shorts, huge Wellington boots to protect against the mud, and a vest worn as a kind of buttoned tank top. The look was so memorable that for Saint Laurent's SS20 there was a "replica" on the runway worn by Kaia Gerber – but Kate Moss's interpretation was also the most essential of a vest-mania that not only took the underground scene by storm but also the red carpets, with the vest appearing on the party girls of the decade like Paris Hilton, Lindsay Lohan, Mischa Barton, Olivia Palermo, Nicole Richie, and even the proto-internet celebrity Corey Kennedy. For men, things were more difficult, let's say: the uniform adopted by stars like Pharrell, Usher, 50 Cent, but also LeBron James or Zac Efron, Johnny Depp, or Chad Michael Murray.

Ann Demeulemeester FW24

Andreadamo SS24

Bally FW24

Balmain FW24

Burberry SS24

Dior Pre-Fall 2024

DSQUARED2 FW24

Emporio Armani FW24

Enfants Riches Dèprimès FW24

Giorgio Armani FW24

Hermès SS24

Loewe FW24

Magliano FW24

MM6 Maison Margiela FW24

Moschino FW24

Sacai FW24

S.S. Daley FW24

Todd Snyder FW24

Tod's SS24

Undercover SS24

Vaquera FW24

Yohji Yamamoto FW24

Zimmerman FW24

The style, in truth, adapted to that mix of boho-chic, disco, and indie aesthetics for womenswear and the new metrosexual look that many men were cultivating, as this was the phase where mainstream and underground clashed. What united the presence of the vest in both men's and women's wardrobes was a tendency towards "dressing-up" that manifested not so much with a revolution of the dominant silhouette but with the addition of formal representative touches on openly modern looks. It's clear that here womenswear had much more room for maneuver compared to menswear, where the vest flattened out into two relatively debatable looks that today have a certain nostalgic charm: paired with a white t-shirt, as seen on the younger stars closer to the teen world; paired with a shirt and tie. In both cases, it was worn over jeans, but in the generally coarse styling atmosphere of the time, accessories were often random, shoes incongruous, proportions disjointed, and fits poorly conceived.

Today, fortunately, the vest seems to have returned in a more disciplined and effective form: worn alone or over a monochrome layer by Loewe and Ann Demeulemeester; reintegrated into more complete outfits by Magliano, Armani, and also Enfants Riches Déprimés, but above all, and even better, transformed into a guêpière dress by Moschino, into outerwear by Sacai, and even into a trompe-l'œil print by Balmain. The best, however, in their simplicity, remain Bella Hadid and Jennifer Lawrence, who wear it as Kate Moss did many years ago. The only rule to always remember, however, is to avoid the pinstripe version, unless you want to look like an old West banker.