How to Wear an Oversized Shirt

Check out this guide on how to style an oversized shirt, the perfect layering piece and a comfortable, casual piece to buff up your capsule wardrobe.

The oversized shirt is one of the most controversial items in all men’s fashion. It defies all the values we often tend to adhere to and is often associated with our girlfriends lounging around our living room having raided our wardrobes for something comfy to wear. But an oversized shirt should not be written off so easily, it can contribute to a number of great styles and is a piece that is incredibly versatile and stylish when worn correctly.

The recent surge in the popularity of oversized shirts and T-shirts is a complete contradiction to many of the values that men hold dear when it comes to their style. Most of us tend to prefer a well-fitted shirt, and it’s drilled into us that the fit is the most important thing when it comes to shopping, especially for shirts. Times they are a changing, however, and a large fitted shirt fits perfectly with the current predilection for playing with silhouettes. With this in mind, we’ve compiled a handy guide on how to pull off this polarizing trend with style.

Men’s Oversized Shirts

The long shirt is strictly an item of clothing for a casual occasion. If you have to wear a shirt to work don’t assume that it’s acceptable to show up wearing an oversized option, as it’ll likely land you in the dog house. In some ways, an oversized shirt totally defies the conventions of traditional fashion and, in a conservative work environment, could be considered a statement piece.

Just because you are wearing an oversized shirt, don’t presume this means you have to up the size of everything else you’re wearing. The best way to compliment the looser look is often with a nicely fitted pair of dark skinny jeans or chinos as the combination creates a good contrast. Besides, if you do opt to oversize your trousers alongside everything else; you’ll likely end up looking a little bigger than you’d probably want to – best to avoid.

The same should apply when it comes to adding layers to your outfit as well. A bomber jacket, or a denim jacket should perfectly compliment an oversized shirt by emphasizing the length of it and adding to the casual nature of the outfit.

Oversized White Shirt

One of the most popular options when it comes to an oversized option, a loose fitted white shirt is widely known as the quintessential ‘day after’ girlfriend attire in cheesy rom-com movies. Don’t let this deter you, though, an oversized white shirt is an incredibly clean, versatile and stylish layer that’s both practical and looks good.

As mentioned above, it’s best to contrast the oversized nature of the shirt with a more fitted bottom half – with skinny jeans being among the best choices. Throw on some smart, but suitably laid-back Dr. Martens to finish the look and, if it’s a sunny day, a pair of iconic Ray-Bans for a summertime flair.

Oversized Checked Shirt

As we all know fashion has a habit of recycling itself and the long oversized shirts are not exactly a new trend. The most iconic use of bigger fitting shirts is perhaps during the grunge era of the early-mid 1990’s. Kurt Cobain was often spotted wearing checked ones in particular. Paired with a pair of stone washed jeans and some Converse or Vans this is the perfect way to capture that 90’s era style.

It’s also a look synonymous with the skater scene, head down your local skate park and you are likely to find several teenagers wearing their baggy shirts effortlessly. Reinforcing that old cliche that it isn’t what you wear, but rather how you wear it that counts.

Oversized Black Shirt

An oversized black shirt is another versatile option that’ll work through each season just as well as the last. Looking great with some buttons undone, as well as over a simple t-shirt it’s an ideal wallet-friendly wardrobe buffer. Once again, it’s important to consider the silhouette of your entire outfit, when keeping things big up top, it’s best to maintain a streamlined look below.

We’ve opted for some trendy washed indigo jeans which will add another element of detail and texture to an otherwise monochromatic look. On your feet, throw on a pair of trainers or elevate the look with some smart Chelsea boots for a suitable ‘night on the tiles’ getup.

How to Wear an Oversized Shirt

The oversized shirt also has its place in modern popular culture as well, One Direction singer Harry Styles is a champion of the look, effortlessly combining them with a pair of skinny jeans and some Chelsea boots to give him his devil may care vibe. He also accessorises with the shirt, combining it with a beanie hat or a bandanna. Sound like you? Learn how to master the Harry Styles look in full.

One of the best ways to pull off the look is to use it as a top layer in a casual outfit. They can often prove the perfect item of clothing for adding depth to your outfit and is great for creating a more laid back style. If you are to wear one with a T-shirt underneath though, make sure it is of a similar length as using a normal sized T-shirt underneath an oversized shirt is not the best look.

If you’re in the midst of the cooler months, simply wearing a larger shirt alone might not be the warmest option at your disposal. To combat this, you can always try wearing it underneath a jumper. This may not sound like a very stylish option, but trust us, it is. Go for a basic coloured jumper, such as black or grey, so you can then add a little bit of colour to your shirt underneath.

Try wearing a navy shirt from Lyle & Scott with a black jumper over the top. Because you’re wearing an oversized shirt you don’t want to tuck it into your trousers, so keep it untucked and poking out from under your jumper. Go for a pair of wider legged trousers for a bang on trend look this season and team the look with a pair of casual and comfortable trainers, Asics have some spot on options available for a cracking look this season.

How to Wear Oversized Shirts

It’s better to contrast an oversized shirt with a slimmer fitted trousers / jeans.
A bomber jacket or denim jacket perfectly compliments an oversized shirt.
An oversized shirt looks great with some buttons undone, as well as over a simple t-shirt.
One of the best ways to pull off an oversized shirt is to use it as a top layer in a casual outfit.

On That Note

An oversized shirt will work perfectly for you this season. It doesn’t matter where you’re wearing one, you can always dress one up or down for a comfortable, on-trend look this season. Of course, there are a few style icons you can always look to for inspiration when wearing an over-sized shirt this season – Harry Styles and Kurt Cobain, perfect for those days when you don’t know what to wear.

Feature image from Pinterest