No matter how much we keep on asking ourselves why Y2K is still happening, it continues to dominate our wardrobes. It’s infested our jeans and made them baggier, turned us googly-eyed whenever something is embellished with a shiny rhinestone, and it’s been bringing back long shorts — some of which go so far down the leg they enter 3/4 length territory.

While the debate on inseam lengths continues online and in our offices, John Cena-style shin slappers that since the early 2000s have been considered a strong no-go have been christened the winner by Y2K aficionados.

The writing has been on the wall for long shorts ever since we started looking at Adam Sandler’s fashion taste through a new lens. The actor embodies IDGAF style and no matter if he’s on the red carpet or being papped running errands, you can expect to find the 55-year-old in a pair of massive shorts.

It’s a style that largely contributed to the actor being the top trending celebrity style star of last year, and people are taking note of the power of long shorts.

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Someone who we have previously conspired to be a big fan of the signature Sandler style is Justin Bieber.  His recent looks have been defined by a bagginess that has not been since the early naughts and he has also brought back shorts back from that era.

The pop star has been going especially oversized with his jeans, a look that he has made summer-appropriate by wearing jean shorts (or jhorts). A style that has been exclusively the domain of OG skaters, the jhort has been going through its own TikTok-inspired renaissance.

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But it’s not only the denim variations of 3/4 length shorts that we are seeing around.

A fellow master of baggy outfits, Angus Cloud has taken a more sporty approach to the look, wearing a baggy pair of Fila shorts with a Soulja Boy-esque sag. And you can’t forget the king and queen of Y2K: Bella Hadid and Marc Kalman.

Ever since the couple made themselves Instagram official, the two have been radiating 90s power-couple energy through their Y2k-heavy looks. This has included Kalman wearing a bunch of super-long patterned shorts along with his favorite Dr. Martens shoes while Hadid has been shunning short shorts in favor of longer variations.



Of course, you can get a similar pair to these by rooting through the bins of thrift shops, but there are also a number of designer options available.

The most reason men’s fashion month saw the of the biggest shows decide to take their selection of shorts to literal new lengths: Givenchy, Louis Vuitton, and Kenzo all presented legwear that hit the sweet spot halfway down the shin for Spring/Summer 2023.




Until those hit shelves in around six months’ time, we have selected some of our favorite long shorts from seasons gone by. Ranging from high fashion labels to workwear classics check out some of the best options available below.

Few things scream early-2000s like a super long pair of jhorts. This pair from We11 DONE look like they’re straight out of a grainy VHS-recorded skate video.

The line between long shorts and cropped trousers is a fine one, and this Charles Jeffrey design finds itself on the side of shorts — but only just.

The dad-core essential: a khaki green pair of long shorts. This version comes courtesy of New York-based collective SC103 and its early-aughts-inspired collections.

 

If experimenting with long shorts is something new for you, then this pair from Y-3 is a great place to start. They’re all black and have a pretty standard slim fit so they aren’t going to attract lots of attention — leaving you to experiment with a new silhouette in peace.

There’s nothing better than buying something and finding out its revesible, you’re basically getting two items for the price of one. These shorts convert from a bold red pair with cut-out panels all over to a more muted solid maroon fabric.

Loewe’s collaborative line with Paula’s Ibiza is an expert in all things summer related so when it starts binging out long-length shorts you know its time to start listening. This casual pair has blue and grey pieces of jersey fabric patchworked aound the design.

This pair of shorts has such extreme pleating that at first glance it looks as though its a skirt, a trick that we’ve seen COMME des GARÇONS play with previous collection.

It’s fair to sar that a pair of Dickies pants is a staple that you can find in most people’s wardrobes and for good reason. The label’s shorts are made from the same hardy material and keep a relaxed-fit.

Something we have to come to expect from Sunnei in recent seasons is a selection of perfectly oversized pieces, and these shorts show that the label continues to deliver.

Want to keep browsing? Head to the Highsnobiety Shop for more products that we love. Highsnobiety has affiliate marketing partnerships, which means we may receive a commission from your purchase.

 

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