How To Wear The Oversized Clothes – Baggy Fashion For Guys

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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.

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.

“As long as it fits on the shoulders, the arm and trouser length, and proportionally at the waist, and the rest of the proportions are correct so it is not too short in the jacket, then a deconstructed oversized suit, especially double-breasted, can absolutely work.”

Buy Oversized, Not Big

Don’t try and cheat the system, either. Other sharp-elbowed shoppers might have nabbed all but one of this season’s must-have suede jackets, but if it’s two sizes too big, don’t just palm it off as oversized, which always works best when it’s been designed to fit that purpose.

“Purposefully oversized pieces provide the additional structure you need to avoid looking like all your clothes have stretched on the hanger which just looks scruffy,” says Murray. “You want the items to be oversized in the correct places, like the shoulders and the waist. Otherwise, you’ll look like a schoolboy who’s not grown into his new school uniform yet, or worse, Donald Trump in a suit.”

Add Balance

As with any statement trend, it’s important to avoid the temptation to go crashing in with all the grace of a reversing dump truck without any tyres on. This style works best when you dip your toes in gently at first, says Murray.

“For the most part, you need to balance out the look with a slimmer fit elsewhere. With an oversized coat, for example, you might want to wear it over a more fitted jumper, tee or shirt and slimmer jeans and have just one item which offers the movement and oversized lines. The same stands for jeans or trousers, try and keep it a normal fit on top, but avoid super skinny as the contrast will look odd.”

7 Ways To Go Big On Oversized Fashion

Oversized Coat

The oversized coat has been beloved by wallflower sleuths ever since Sherlock Holmes swung a cape over his shoulders and stuck a deerstalker on his bonce. Follow the detective’s lead on this one.

When you’re going big with fit, go easy on colour. Neutral shades like grey, white and navy work best, while brighter tones will have you looking like a sleazy soul singer finishing up a bender in the local strip club.

Oversized technical coats, puffer jackets and parkas work, but wool overcoats best lend themselves to a more flowing silhouette. Underneath, keep the silhouette sleek with roll necks and cropped trousers, and keep a little of below on show so no one is worried about what you are wearing (or lack thereof) under wraps.

Oversized T-Shirt

Skatewear is streetwear and streetwear is high-fashion, so thanks to some basic mathematics, baggy tees – a favourite of those ollie 360 flipping boarders – are now high-fashion.

A minimal, neutral tee will stand you in slicker menswear stead than any Grateful Dead band merch, but don’t be afraid of a pop of colour as long as you’re balancing it down below.

Usual rules about the oversized T-shirts sleeve hitting the middle of the bicep don’t necessarily apply here, with some cuts falling as low as the elbow. Just maybe consider adding a few rolls to the hem to avoid your arms looking weedy.

Oversized Jumper

A jumper is probably the easiest item of oversized clothing to wear – who could blame you for cocooning yourself in knitwear for winter? It’s a look that can be as grungy as it is cosy countryside, though.

As the likely second line of defence under a jacket or coat, it’s easier to work colour and pattern into an oversized jumper than other items of clothing. If you do opt for something attention-grabbing up top, keep it balanced with a simple pair of trousers below, which should hit the sartorial sweet spot on fit: not too wide, not too skinny.

Standard crew necks aren’t the only option here either. An exaggerated roll neck can look (and feel) especially warm and inviting when the weather outside becomes harsher.

Oversized Suit

You don’t need to be a menswear expert to know that wearing a zoot suit is an acquired taste (and a bad one at that). However, power dressing is once again back in the boardroom, so it pays to know how to make the hire.

If you are going to amp-up your tailoring, remember that the basic principles of fit still count. That means the jacket should slope down the shoulders and the sleeves should finish above the top of your wrist bone.

To bring the look out of the 1980s, consider dressing down a boxy double-breasted suit by wearing the jacket open over a plain T-shirt, or by using separates to break the outfit up.

Oversized Trousers

Baggy jeans and trousers? That’s madness, you say. But there is a way to do it and not look like a sack of potatoes.

First things first, go cropped. Most of the time, bunches of excess fabric at the hem tend only serves to look less messy. If there is a break, aim for just one full break and make sure the back of the trousers isn’t sweeping the floors. Pleated trousers are a great option in this category – on trend, and as part of the 1950s comeback, they sit above the waist for a flattering fit while the trouser fabric neatly flows down below.

The thicker fabric on jeans means they won’t glide as effortlessly as you strut, but their unfussy demeanour means they work great in workwear ‘fits like a sturdy camel chore coat with a layered shirt and T-shirt underneath (trucker cap optional).

Oversized Hoodie

I said to hip-hop, hippie to the hippie, you’re going to have to buy an oversized hoodie. Everyone in the rap game from Travis Scott to Kanye West is touting them, the blown out of proportion shape suiting the larger than life personas.

Black is a favoured go-to, probably because it hides all the shadows from the rounder parts of your frame (love handles be gone) so the eye can focus on just the shape of the fabric and not of you.

Logos and graphics can work, but unless you’re a regular hypebeast, keep these to a minimum – a simple script logo is enough to show people that you’re clued into the best brands about. Be warned though, it will never work for smart casual occasions so works best next to other casual favourites like jeans and sneakers.

Oversized Shirt

Try and stay away from the high fashion side of things with this one – dress shirts without cufflinks billowing limply just looks like honey shrunk you with her ray gun. However, a patterned or plaid shirt over the top of a simple tee with the sleeves rolled up (droopy cuffs are a no-no) always works as long as there is some hardwearing denim down below.

Longline shirts can work with a slim-fitting jacket over the top to emphasise the length while keeping the upper body in check. The same goes for a jumper. If your shirt fabric is peeking out below a jumper keep the shirt in one colour – it will look odd having a floating paisley pattern around your crotch.

If opting to go for an oversized short-sleeve shirt, Cuban collars work mainly because the slouchy holiday look will never go out of vogue, but best to go wide with the trousers too. You’re on your holidays, so let it all out.