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Style Advice

How to pull off the oversized trend

How to pull off the oversized trend

From loose-fitting outerwear and knits to baggy trousers and chunky trainers, the oversized trend is literally taking up more and more of the fashion space. If you’ve written it off out of fear that it will make you look like you’ve bought too big or are larger than you are, we encourage you to reconsider. By nailing the proportions and pairing appropriately, you can seamlessly integrate the trend into your winter wardrobe. And you’ll be glad you did – it doesn’t get cosier than this. 

“It’s not a matter of buying a size too big,” says stylist Alexander McCalla. “If you take an item that you’d usually buy in medium and choose a large, it’s going to be mis-proportioned and will probably make the rest of your outfit look odd.”

Instead, go for pieces that have been designed to be oversized and style them with simpler shapes. For example, a large knit will look extreme when paired with skinny jeans, but slim-fit trousers will keep the look in proportion and complement the oversized style.

Much of today's oversized clothing is rooted in streetwear, which makes that aesthetic an easy place to start. It's also worth noting that oversized pieces lend themselves best to a more chilled and casual aesthetic, so make sure it’s the most relaxed element of your outfit. And when styled thoughtfully, the oversized trend can also serve as a nice opportunity to play with expectations. Overcoats may seem more formal, but by choosing one with an oversized silhouette, you’re lending it a laid-back edge.

“If you’re looking for an oversized overcoat, Timothy Everest get the shape right,” Alexander says. “The unstructured shoulders and extended sleeves mean it flows neatly over your body. The length should be to your knees or lower to avoid looking too wide on the sides.”

Baggy knits are another cosy winter favourite that lends itself best to casual wear, so pair yours with slim jeans or relaxed trousers for an easy weekend look, and avoid the urge to smarten it up too much. The shoulder seam should fall slightly lower than usual, but the sleeve should still come to your wrist rather than over your hand, and the hem should be fitted to your waist. The body should be loose and free-flowing, but not so long that it looks like a dress. 

Photographed: GANT Beaumont Low Lace Shoes (£112)

If you’re looking to make a statement with chunky shoes, always buy your true size – unless your style icon is Sideshow Bob. The impact of an oversized shoe is in the weight and chunkiness of the sole. Chunky derbys with an industrial-style commando sole fool the eye into believing the shoe itself is oversized and will bolden your aesthetic without looking too big. 

Like baggy knits, chunky trainers don’t look great with skinny jeans, as they throw your bottom half out of proportion. Opting for a slim fit will make a big difference, or if you’re into the 90s look and want to nod to the skater trend, loose fit jeans can work with bulky trainers too.


Words: Ella White
Photography: Jamie Stoker
Styling: Alexander McCalla