Having worn a variety of oversized fits over the past couple of years, Justin Bieber is the celebrity poster boy of Y2K style. And central to his look is his decisively XXL denim selection.

Puddling over the artist's choice of footwear to the point where it is almost completely obscured, his jeans seem to be getting wider with every outfit that he wears. Throughout the late 90s and early 2000s, hip hop and skateboarding culture brought baggy jeans to the fore, and, true to fashion's cyclical nature, they have found themselves back in the limelight.

Y2K was a definitive fashion era: Kanye West was still the Louis Vuitton don, Nigo and Pharell had taken over the streetwear market with Billionaire Boys Club, and Supreme's streetwear revolution was in its infancy in New York. For those who were there, watching y2k style be appropriated by Gen Z on TikTok is a strange phenomenon. For those in Gen Z, it is the joke that keeps giving as there is a seemingly endless bank of peculiar trends and fads to adopt in a post-ironic manner. Styles such as rimless shades and bejeweled graphics have transitioned from being bad taste to being so bad it's good.

Our obsession with the late 90s/early 2000s knows no limits. We’ve had Adam Sandler being crowned the top trending celebrity style star of 2021 and Ed Hardy making a timely return through a collaboration with London streetwear label Unknown. And Jeans have been central to this craze, with low-rise styles having officially made a comeback and the purveyors of the coolest styles from the era such as the Japanese label’s Evisu and Bape flying off Depop’s virtual shelves.

It is a quintessential part of fashion from the time. Let's not forget that this is a time when Justin Timberlake rocked a full denim suit on the red carpet, complete with a denim hat. And his partner at the time, Britney Spears, matched his look with her own denim dress and bag.

The peak of the oversized denim obsession came from JNCO, whose super wide-leg designs made the label one of the 20 most popular brands favored by young men in 2000.

If you are similarly obsessed with the Y2K look, take a look through Bieber’s recent outfits for inspiration on how he makes the era’s baggy jeans work.

Bieber's got good news

Fresh from spending an eye-watering $1.3 million on a Bored Ape NFT, Bieber was spotted out with wife Hailey for brunch. While he might be investing in the future of how art is collected, the musician's fashion remained firmly in the 90s as he rocked a pair of wide-leg, washed-out black jeans, and an oversized hoodie.

Collegiate Hoodie

Collegiate Hoodie

$120

Highsnobiety

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Trompe L'oeil Wide-Leg Jeans

Trompe L'oeil Wide-Leg Jeans

$1350

Balenciaga

Buy at Farfetch
Air Jordan 4 Retro SP Union Desert Moss

Air Jordan 4 Retro SP Union Desert Moss

$439

Nike

Buy at Stadium Goods

Grunge Inspired

Of course, the only thing to balance out a hugely oversized pair of denim is an equally huge piece of knitwear. With his oversized cardigan and white sunglasses, Bieber is channeling a Kurt-Cobain-Esque grunge aesthetic. A possible ode to one of the most influential subcultures, Bieber is, once again, swallowed alive by his XXL outfit.

Staples Beanie

Staples Beanie

$17

Highsnobiety

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Cardigan

Cardigan

$505

Acne Studios

Buy at Highsnobiety
Carpenter Jeans

Carpenter Jeans

$94

OBEY

Buy at Urban Outfitters

The Hoodie and blazer combo

For many of those who attended schools where a blazer was part of the uniform, the contrast between a hoodie and a blazer is an uneasy but familiar sight. For the NBA players who attended formal sports prep schools, they also started to make the unlikely pairing to keep warm in the winter and brought the look into the NBA when becoming professionals in the late 90s and 00s. Causing a relatively small style moment at the time, it’s been brought back by a new generation of NBA stars such as Russell Westbrook and LeBron James.

Bieber’s 2021 MTV Video Music Awards look takes the hoodies and blazers trend and matches it with a pair of wide-leg jeans to add an extra hit of Y2K imitation.

Classic Logo Fleece Hoodie

Classic Logo Fleece Hoodie

$115

Highsnobiety

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Double-Breasted Blazer

Double-Breasted Blazer

$742

Dries Van Noten

Buy at mytheresa
Loose Fit Jeans

Loose Fit Jeans

$330

Acne Studios

Buy at Highsnobiety

Vintage Gorpcore

Bringing together two of the biggest trends from the past few years, gorpcore and Y2K meet in this relaxed outfit. With an orange fleece jacket paired with wide-leg jeans and a pair of converse chuck 70s, the geography teacher’s staple school-trip uniform has never looked better.

CTAE Full Zip Fleece

CTAE Full Zip Fleece

$355

The North Face

Buy at The North Face
Large Baggy Jeans

Large Baggy Jeans

$1050

Balenciaga

Buy at Balenciaga
Chuck 70

Chuck 70

$105

Converse

Buy at Highsnobiety

A Grey Day

While this super baggy pair of dark wash denim would likely cover almost all of the sneaker, that doesn't stop Bieber from appreciating the Nike x Patta Air Max 1. Switching from the blue wash jeans we have seen him in most regularly, this time he opts for a dark pair of overwashed, oversized denim and matches it with ERL's signature hoodie style.

Cashmere Recycled Beanie

Cashmere Recycled Beanie

$105

Pangaia

Buy at Pangaia

Ashfield Hoodie

$140

Carhartt WIP

Buy at Highsnobiety
Brutus 2021M Boot Cut Jeans

Brutus 2021M Boot Cut Jeans

$345

Acne Studios

Buy at Highsnobiety

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