How To Wear Make The Oversized Trend Work

There was a time when wearing clothes so baggy that you needed a staple gun to keep them on was more about your mother making sure you could get through puberty in the same school blazer. However, if you graduated within the last 15 years, you probably grew up wearing clothes that were designed to be slim and flattering – clothes that didn’t just hang on your shoulders. Menswear has been dominated by skinny cuts for the majority of the twenty-first century.

Around the mid-2000s, men’s wardrobes were shrink-wrapped under the influence of Hedi Slimane at Dior Homme and later Saint Laurent. It was all muscle shirts, slimline tailoring, and indie bands in everything skinny-fit. However, the fashion pendulum has swung back in recent years. It was partly a reaction to what had come before, but the oversized trend also coincided with the mainstreaming of hip-hop fashion and athleisure. Kanye West’s longline tees and chunky hoodies were one part of the look, while Kim Jones, Demna Gvasalia, Patrick Grant, and Virgil Abloh wore billowing suits.

This is comfort as fashion, as opposed to spray-on jeans and nip-and-tuck tailoring. Wide-leg trousers, slouchy blazers, boxy tees, and blanket coats are all on trend right now. It’s not that oversized clothing can’t be tailored; it’s just that they’re more louche. However, thinking it’s something new would be a mistake. Wider slacks are a throwback to the 1950s, while dad jeans are a throwback to the 1990s, and power suits are a throwback to the 1980s. Oversized has always been a fashion statement, and it’s one that a lot of people are making right now.

How To Make The Oversized Trend Work

Know The Occasion

Although the oversized trend is popular right now, it is not appropriate for all occasions. That isn’t to say you can’t wear it for a more sophisticated look. Take, for example, the Armani-style Italian suits, which are often cut generously and softly. A deconstructed oversized suit, especially double-breasted, can absolutely work as long as it fits on the shoulders, arm and trouser lengths, and proportionally at the waist, and the rest of the proportions are correct so it is not too short in the jacket.

Buy Oversized, Not Big

Don’t even try to game the system. Other astute shoppers may have snatched up all but one of this season’s must-have suede jackets, but if it’s two sizes too big, don’t dismiss it as oversized, which always works best when it’s been designed for that purpose. Oversized pieces provide the extra structure you need to avoid looking like all of your clothes have stretched on the hanger, which just looks scruffy. The items should be oversized in the right places, such as the shoulders and waist. Otherwise, you’ll appear like a schoolboy who hasn’t yet grown into his new school uniform, or, worse, Donald Trump in a suit.

Add Balance

As with any statement trend, it’s important to resist the urge to crash into it with the grace of a reversing dump truck with no tyres on. This style works best when you begin by gently dipping your toes in. The majority of the time, you’ll need to balance out the look with a slimmer fit elsewhere. When wearing an oversized coat, for example, you might want to layer it over a more fitted jumper, tee, or shirt and slimmer jeans so that you only have one item that offers movement and oversized lines. The same is true for jeans or trousers; try to keep the top a normal fit, but avoid super skinny as the contrast will look odd.

Ways To Go Big On Oversized Fashion

Oversized Coat

Since Sherlock Holmes swung a cape over his shoulders and stuck a deerstalker on his bonce, the oversized coat has been a favorite of wallflower sleuths. On this one, follow the detective’s lead. When it comes to fit, go light on the color. Brighter tones will make you look like a sleazy soul singer finishing up a bender in the local strip club, while neutral shades like grey, white, and navy will make you look like a sleazy soul singer finishing up a bender in the local strip club.

Oversized technical coats, puffer jackets, and parkas are all appropriate, but wool overcoats are best for a more flowing silhouette. Keep the silhouette sleek underneath with roll necks and cropped trousers, and show a little of your lower half so no one is concerned about what you’re wearing (or not wearing) underneath.

Oversized Tee

Skatewear is streetwear, and streetwear is high-fashion, so baggy tees, a favorite of those ollie 360 flipping boarders, are now high-fashion thanks to some basic math. A simple, neutral tee will serve you better than any Grateful Dead band merch in terms of menswear, but don’t be afraid to add a pop of color as long as you keep it balanced down below. The usual rule that the sleeve of a T-shirt should hit the middle of the bicep does not apply here, with some cuts falling as low as the elbow. To keep your arms from looking weedy, consider adding a few rolls to the hem.

Oversized Jumper

Who could blame you for cocooning yourself in knitwear for the winter? A jumper is probably the easiest item of oversized clothing to wear – who could blame you for cocooning yourself in knitwear for the winter? However, it’s a look that can be as grungy as it is cosy country. It’s easier to work color and pattern into an oversized jumper than other items of clothing because it’s the likely second line of defense under a jacket or coat. If you go for something bold on top, balance it out with a simple pair of trousers on the bottom, which should hit the sartorial sweet spot in terms of fit: not too wide, not too skinny.

Here, too, standard crew necks aren’t the only option. When the weather outside gets colder, an exaggerated roll neck can look (and feel) especially warm and inviting.

Oversized Suit

Wearing a zoot suit is an acquired taste, even if you’re not a menswear expert (and a bad one at that). However, power dressing is making a comeback in the boardroom, so knowing how to make the hire is essential. If you’re going to step up your tailoring, keep in mind that the fundamentals of fit still apply. That means the sleeves should end above the top of your wrist bone and the jacket should slope down the shoulders. Consider dressing down a boxy double-breasted suit by wearing the jacket open over a plain T-shirt or by breaking up the outfit with separates to give it a 1980s vibe.

Oversized Trousers

Trousers that are too big? You say that’s insane. There is, however, a way to do it without looking like a sack of potatoes. First and foremost, get cropped. Bunches of excess fabric at the hem, for the most part, only serve to make the hem look less messy. If there is a break, try to take only one full break and avoid sweeping the floors with the back of your trousers. Pleated trousers are a great option in this category because they sit above the waist for a flattering fit while the trouser fabric neatly flows down below. Pleated trousers are on trend and part of the 1950s comeback.

Jeans’ thicker fabric means they won’t glide as easily as you strut, but their unfussy demeanor means they’re perfect for workwear, fitting like a sturdy camel chore coat with a layered shirt and T-shirt underneath (trucker cap optional).

Oversized Hoodie

I told hip-hop, “You’re going to have to buy an oversized hoodie,” and “You’re going to have to buy an oversized hoodie,” and “You’re going to have to buy an oversized hoodie,” and “You’re going to have Everyone in the rap game is promoting them, from Travis Scott to Kanye West, with the out-of-proportion shape fitting the larger-than-life personas. Black is a popular choice, owing to the fact that it hides all shadows from the rounder parts of your frame (love handles be gone), allowing the eye to focus solely on the shape of the fabric rather than on you.

Logos and graphics can be effective, but unless you’re a regular hypebeast, keep them to a bare minimum – a simple script logo is enough to demonstrate that you know what’s hot. However, it will never work for smart casual occasions and is best worn with other casual staples such as jeans and sneakers.

Oversized Shirt

Dress shirts without cufflinks are a good example of staying away from the high fashion side of things. Honey must have shrunk you with her ray gun because you’re billowing limply. A patterned or plaid shirt over a plain tee with the sleeves rolled up (droopy cuffs are a no-no) always looks good, as long as there’s some hardwearing denim underneath. Longline shirts can be worn over the top of a slim-fitting jacket to emphasize the length while keeping the upper body in check. The same can be said for a sweater. If the fabric of your shirt peeks out from beneath a sweater, keep it in one color – a floating paisley pattern around your crotch will look odd.

If you’re going for an oversized short-sleeve shirt, Cuban collars are a good choice, mainly because the slouchy holiday look never goes out of style, but it’s also a good idea to go wide with the trousers. Let it all out while you’re on vacation.