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Style Advice

The dos and don’ts of oversized dressing

The dos and don’ts of oversized dressing

In the midst of a pandemic, comfort is key. The good news? It’s a legitimate style choice that you can adapt for your everyday wardrobe, too. Over the past year, our approaches to dressing have changed in one way or another: some of us have grown (almost literally) attached to our sweatpants, while others are valiantly clinging to a semblance of their normal style. But one thing can be said of us all – keeping comfortable has become a top priority. 

The upside is that it’s not so hard to incorporate comfy clothing into your day-to-day look without falling back on your scruffy old hoodie. Thanks to the oversized trend – which has unsurprisingly seen a recent surge in popularity – you can pull off loose fits and call it a style choice rather than slobbiness. We know what you’re thinking – nailing a specific look isn’t as easy as throwing on your baggy favourites and calling it an outfit. So to help you navigate the oversized pitfalls, we’ve compiled a handy list of the dos and don’ts of this slightly intimidating style so you can pull it off perfectly.

Do ease in

If you’re just dipping your toe into the oversized pool, the easiest place to start is with trends that already suit this style of dressing. For example, streetwear, skater style, and ‘70s-inspired looks (and probably more that don’t begin with ‘S’) all lend themselves nicely to oversized cuts. You don’t want to dive straight in with a fully-oversized look, so considering how to adapt areas of your existing style without stepping too far out of your comfort zone will make the transition much easier. 

Looser clothing tends to feel more casual, so make sure your oversized piece is the most relaxed element of your outfit. If you usually dress quite smart, rocking a huge Kanye-style t-shirt and chunky trainers for your first foray into oversized dressing might look a bit weird. Instead, ease in. So if you’d normally wear a t-shirt and chinos on the weekend, pick one piece or the other to try in an oversized style first. When you start to feel more confident in oversized pieces, like relaxed-fit trousers and baggier tops, you can gradually increase the size.

Do consider proportions

Once you’ve set your sights on the right oversized look for you, you need to know how to actually wear it well – and that’s all about proportion. For example, skinny jeans with a big baggy top and/or chunky Balenciaga-style trainers will throw your legs out of proportion and make your whole look seem off-balance. In fact, for this look it’s best to remove skin-tight styles from your repertoire, as they just won’t work with the proportions of your oversized pieces. The trick is to make your oversized item the centre of your look, so pairing it with another extreme fit will be distracting. 

Instead, try a big knit or oversized top with slim-fit trousers. They don’t look as severe and will maintain the right proportions while complementing your oversized top. Slim or tapered trousers will also allow you to dip your toe into chunkier footwear without making your feet look comically large or clown-like. The impact of oversized footwear is all in the chunkiness of the sole, so it’s important that your trousers complement this without taking the emphasis to the extreme.

Don’t just buy too big

Buying a piece that you’d usually wear in a medium and picking a large will throw off your proportions and drown you out rather than flattering your shape. This is the key distinction between oversized clothing and clothing that’s just too big – and don’t think nobody will notice. You don’t want to look like you’re showing up on the first day of term in a new school jumper.

Key giveaways of a top that doesn’t fit are the shoulder seam hanging a few centimetres too far from your shoulder, the sleeve falling over your hands, and the body feeling boxy rather than loose and free-flowing. A top that’s truly oversized by design will fall lower on your shoulder (raglan style rather than set-in), but the sleeve will still finish at your wrist, and the hem will still fall in line with your body. 

When it comes to trousers, it’s not so easy to skimp on the correct style as you still need the waistband and length to fit you correctly. So look to relaxed-fit, or even wide-leg styles that are designed to look bigger but still fit your exact size – and as we mentioned before, maintain proportions with a slimmer cut on top.

Don’t overthink it

We know: it sounds like there’s a whole lot of rules and not much fun to be had when it comes to oversized dressing. But, if anything, there’s actually more room to play with all the different ways to wear oversized style. So once you have the simple ground rules in place – buy truly oversized pieces, consider proportions, and keep it casual – it’s a great way to experiment with the expectations of your wardrobe. 

An easy way to make your oversized outfit feel interesting is to combine different styles in one. Since you already know that larger items lend themselves best to a chilled-out aesthetic, resist the urge to smarten up and instead find ways to bring oversized smart pieces into your casual wardrobe. For example, an oversized overcoat feels less formal than a sleeker cut, and can easily be paired with relaxed pieces. Likewise, pairing formal trousers with an oversized top or jumper will make them feel instantly dressed down so you can wear them in relaxed settings too. Comprende? Cool – now you’re ready to go big.


Words: Ella White