How To Wear Oversized T-shirts (Guys Edition)

Baggy streetwear is in, and t-shirts are no exception. However, pulling off the oversized look isn’t as easy as buying your clothes two sizes too large – there’s more to it if you want to look chic and edgy. So many guys ask, how do you wear an oversized t-shirt?

Buy a t-shirt in your standard size in a relaxed or oversized style. The hem ends between your hips and the bottom of your crotch; the sleeves can fall to your elbows. Guys’ oversized t-shirts are casual and look best in slouchy outfits or when contrasted with narrow trousers.

Now that we’ve grasped the basics of the oversized t-shirt, we can perfect the look. Once you’ve gotten used to it, you’ll find that baggy clothing is remarkably comfortable, versatile, and attractive. The rest of this article will help you get there, focusing on the essential streetwear piece of the oversized t-shirt.

Outfit Ideas Using Oversized T-shirt For Guys

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Source: Unsplash

Simple is better with an oversized tee. Although logos and other merch can work on a baggy shirt, we don’t recommend it. You’ll limit yourself to far fewer outfits wearing a graphic t-shirt with a complex design. Especially if you’re new to the style, a plain tee is better.

Neutral colors pair well with nearly any outfit, and minimal designs are never offensive. So, you can’t go wrong with a plain white oversized t-shirt. That’s the most versatile choice, freeing you up to experiment while still looking good.

Another thing to note is the cut: Not baggy tees are identical. We recommend buying a shirt that’s your size but in an oversized or relaxed fit style. That way, your shirt will fit you comfortably and hang down in the ways it is designed to, not all over.

What’s ideal is a t-shirt that’s loose around your torso and sleeves but isn’t overly long. If the hem ends between your hips and the bottom of your crotch, it should be good.

Likewise, look out for a drop shoulder seam. This detail might seem insignificant, but it goes a long way to making your streetwear look realistically baggy.

It’s best to buy a loose t-shirt with a slightly heavier fabric. It’ll look less wrinkled when you wear it, which can become an issue with oversized lighter materials. Not only that, but the weightier fabric will sit on your body in a structured way.

Now let’s look at some outfits that let you show off an oversized t-shirt.

Plain And Simple Look

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Source: Pexels

The easiest way to wear an oversized t-shirt is to pair it with skinny jeans and low-cut sneakers. You can complete the look with simple accessories – a beanie or cap depending on the weather, plus some tasteful jewelry.

This outfit is excellent for everyday wear. It is effortlessly hip. The contrast between the long and wide t-shirt and the slim jeans is striking but never overstated or loud. Likewise, if you want another top layer, go for a cropped jean jacket to carry on the simple theme.

Not only that, but this combo is one of the few times you can get away wearing a baggy shirt with designs. Because the outfit is so simple, you’ve got an excellent opportunity to highlight your t-shirt and whatever’s on it.

Match It With A Sweater Vest

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Source: Pexels

If you’ve ever seen Friends, you know what we’re getting at here. Chandler and his sweater vests are trendy again – there’s no better time to pick one up and show it off.

This outfit is relaxed but also a little intellectual – it has class. Throw your sweater vest over your baggy t-shirt, and complete the look with a loose pair of trousers or jeans. Depending on your sweater vest’s material, corduroys are an excellent choice.

Remember to wear a long-sleeve oversized shirt for this look – and make sure not to wear a V-neck shirt and a V-neck sweater. Keep at least one round-neck in the mix.

Layer It With A Blazer

Try layering your oversized t-shirt under a sports coat if you need a slightly more formal look. Add a tighter cut of jeans or trousers into the mix, and you might get away with this outfit at the office.

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Tucking your t-shirt in is up to you with this look, but we think it looks more striking untucked or with a French tuck. Doing so shows everyone you intentionally chose a baggy tee, not a random shirt out of your closet.

Hats also work great with this outfit – consider a fedora if you’ve got one.

Go For Slouchy

Sometimes though, you want to look as chill as you feel. In that case, slouchy is your best bet: Pair your oversized t-shirt relaxed-fit jeans, joggers, or tracksuit pants.

Keep your t-shirt untucked, your clothes well-ironed, and consider an exciting pattern for your trousers too. When done well, this look is great for all body types. It’s comfortable and approachable while still managing to be chic.

To truly take this outfit to the next level, you could add subtle jewelry or a baseball cap. The trick is to remain casual while showing off the quality of your clothes and the slouchy silhouette they create.

Highlight Your Waist

Men can do an hourglass figure too – and the oversized t-shirt is a vital piece to making this boxy outfit succeed. Complement it with straight-cut trousers or jeans.

This time, tuck your shirt in and hike up your trousers too. Since your t-shirt is so baggy, it’ll add some bulk to your top half and give you an hourglass look when combined with your looser jeans.

Finish the look with chunky sneakers or low-cut boots for the best effect. A belt is optional, but it risks making you look too formal or too immature. Rock this look for casual occasions, especially when you want to stand out.


In summary, there’re many ways for guys to wear an oversized t-shirt. They look best in casual outfits, contrasting a slim lower half or flowing together with other relaxed clothes.