Guide to the oversized fit

How to put together roomy attire, from slouchy jackets to wide-leg pants, with finesse.

A surefire way to feel larger than life is to wear upsized clothes. But tactlessness can mean tackiness, which is why we’ve compiled this set of foolproof ways to throw it all together with a sense of ease to match your look.

Effortlessness, comfort, and style collide in the oversized outfit. In an effort to pull off that tricky combination, though, you could easily find yourself pillaging your wardrobe with wild abandon, wondering if the oversized look’s purported comfort and convenience is nothing but a fiction. We know how you feel, but there’s no need. These simple tips and tricks will have you saying, with full honesty, “Thanks! I just threw it on.”

The sweater vest

The straight-A student’s favourite item is getting an update. The sweater vest has made a comeback in a less fitted (read dorky), more baggy and bold form. Complementing statement items like this one with more fitted garments – a tee with a matching collar or a pair of tailor-made pants, perhaps – makes for a classy contrast of texture and movement. That said, try to avoid reaching for the skinny jeans or tight-fitted shirt. Just a little bit of contrast goes a long way, while too much can result in an awkward lopsidedness. Balance is key.

Go big or go home

When you want to pair oversized items without compromising elegance, pinning down the right colour combination should be your go-to technique. Muted, organic tones – black, beige, grey, and white – make for a more tailored overall appearance. Especially if you’re opting for sweatpants or relaxed activewear, consider rounding off the ensemble with a slick pair of sneakers and some jewellery, which can offer refined embellishment for a more sophisticated finish. 

Cut and tailored

Whether you’re purchasing jeans or jackets, oversized doesn’t simply mean buying a few sizes bigger than the one you wear. Garments marked oversized are most often tailored to maintain structure despite their loose appearance. When picking out an oversized jacket, keep in mind that a droopy collar and crumpled sleeves won’t have you looking nearly as cultivated as angular shoulders and deep pockets. Oversized items cut with care often help to enhance your frame, leaving more room to play with slouchy pants and everyday tees without risking scruffiness.

Not too shabby

No matter how much we might miss the old Kanye, there’s no denying that Yeezy took minimalist comfort and slotted it into the ranks of high fashion. Though we don’t advise wearing a tracksuit to a formal event, sweatpants and hoodies have nonetheless taken on a whole new essence in recent years. No longer the shabby choice for a wintry day of lounging on the couch, tracksuits are officially a comfortably cool option with character and presence. For a cleaner overall appearance, keep the bright colours and flashy logos to a minimum, and limit accessories to hats and bags so that they don’t get hidden under cuffs.

When you wear oversized clothes, grandeur isn’t a delusion. As long as you stick to a neutral palette, create some contrast, and make seams and shoulderpads work in your favour, convenience and class can go hand in hand.