90s oversized: then vs now

Unless you were at Spring Break 2000, you won’t care that Eminem’s outfit is technically not from the 90s. And, as this is pretty much what the rapper wore for the entire decade, we're overlooking exact chronology for this look. Eminem had big tees, trews and hits aplenty across the 90s and 00s and this straight-off-the-basketball-court getup embodies his style during the era. If you needed more evidence that this vibe didn’t die at the end of 1999, look no further than Justin Bieber. This kid doesn’t own a tee that stops above his knees and his love for ever-longer lines has defined his signature style.

 Winner: Bieber. His lines are longer, leaner and layered.

Few people could own an oversized sweatshirt like Tupac. The rapper was not afraid of colour and this vintage coordinated cap and jumper combo is still hot sartorial property today. The ultimate hip-hop uniform, no one wore sweats that came anywhere near their actual body size in the 90s and, naturally, in 2016 it’s Kanye West who is reaffirming them as a streetwear classic. Following two seasons of muted hues, this year Yeezy made his collection of oversized pieces pop, layering all the clothes in a range of bold new colours.

Winner: Tupac. We’ve got nothing but California love for that big red sweat.

Here’s 90s Jared Leto as Jordan in season one of My So Called Life in a big blue checked shirt, ready for his face to be plastered over a thousand teenagers’ bedroom walls. It is a very good shirt. These days, A$AP Rocky is our plaid poster boy for wearing it all at once, or open over a tee like this. Like Leto, he knows how to work the camera to best show off his look but his comes with a side serving of Flacko steez.

Winner: It’s a draw. Young Leto is about the only guy who comes close to 2016’s MVPP (Most Valuable Plaid Player).

Larry Clark’s 1995 film Kids is celebrated for many things, but today we're recognising its contribution to skate style. Casper’s (Justin Pierce) wide-leg trousers were coveted by every lad worth his skater salts in the 90s. Nowadays, although wide-leg trousers were big at the AW16 shows, the A-list have been slower on the uptake. Cue Kanye at the 2015 MTV Video Music Awards. His big, bunched-up trousers are the first step to welcoming oversized trews back into our wardrobes.

Winner: Larry Clark's Kids. Their look defined the decade.