Men's fashion guides

How To Wear The Oversized Trend And Still Look Tailored

There was a time when wearing clothes so baggy they needed a staple gun to stay on was less of style move, more your mum making sure you could make it through puberty in the same school blazer.

But if you graduated any time in the last 15 years, chances are you grew up to enjoy clothes that were designed slim and flattering – clothes that didn’t just hang on your shoulders. For the majority of the 21st century, menswear has been dominated by skinny cuts.

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Under the influence of Hedi Slimane at Dior Homme and later Saint Laurent, men’s wardrobes were shrink-wrapped around the mid-2000s. It was all muscle shirts, slimline tailoring and indie bands in skinny-fit everything. But in recent years, the fashion pendulum had swung back.

It was partly a reaction to what came before, but the oversized trend also went hand-in-hand with the rise of hip-hop fashion and athleisure into the mainstream. Kanye West’s longline tees and chunky hoodies were one part, the billowing suits of Kim Jones, Demna Gvasalia, Patrick Grant and Virgil Abloh another.

Compared with spray-on jeans and nip-and-tuck tailoring, this is comfort as fashion. Wide-leg trousers, slouchy blazers, boxy tees and blanket coats. Not that oversized clothes can’t be tailored, but they’re certainly more louche.

It would be a mistake to think it’s something new, though. Wider slacks are bastions of 1950s style, dad jeans are right out of the ’90s, while power suits are ingrained in the 1980s.

Oversized has always been a statement, and just now it’s one that a lot of the fashion world is making.

Supersize Me: How To Make The Oversized Trend Work

Know The Occasion

The oversized trend might be big right now, but it’s not something for all occasions, says stylist Sarah-Ann Murray, who has dressed the likes of Samuel L Jackson, Stanley Tucci and Jonah Hill. “I’m not convinced it works as eveningwear which is usually the most formal of occasions. That’s not to say you can’t wear it for smarter looks though. Take the Armani-like Italian suits, which are often a generously-cut soft style.

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