7 Foolproof Ways to Style Oversized Shirts


They're easy, breezy, and comfortable.

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Oversized shirts are a menswear hit this summer, and I’m all for it. Not only do they look great, but they’re an effective way to stay cool. Who doesn’t like the feeling of a gentle breeze flowing across loose shirts in the scorching summer heat?

It’s a world away from a stifling slim-fit shirt. That’s why I recommend at least trying out an oversized shirt if you haven’t yet made the switch.

But while oversized fits look easy-going, it is not an entirely effortless look to pull off. And there’s a fine line between an oversized fit and an ill fit.

This article is here to help. I’ll go through all you need to know about how to style an oversized shirt for men.

How to Choose an Oversized Shirt?

Before you can style an oversized shirt, you need to choose one. So here’s a couple of things that you should keep in mind as you hunt for your oversized summer wardrobe.

Oversized, not Big

As mentioned earlier, there’s a fine line between an oversized fit and an ill-fitting shirt so you need to identify the difference between oversized and big.

You don’t want your shirt to swallow you so don’t go for shirts that are way off your size. Always buy oversized clothing in your usual size because it is the ‘oversized cut’ that gives off a boxy shape and fits loose in the right places.

Casual is Safest

Justin Beiber may think otherwise, but oversized shirts tend to look best in casual settings. They rarely result in a crisp and spruced-up look. Avoid wearing them in formal situations unless you’re really confident in your look.

Slim Fit in Larger Sizes

To be clear, oversized is a specific type of fit. You shouldn’t just buy a larger size of the regular slim-fit shirts you buy.

Slim-fit clothes are essentially based on a body-hugging cut, whereas oversized clothing is designed in a way that looks baggy but still adds ample structure to define your look.

Oversized in the Correct Places

If you’re going for a shirt that’s not necessarily an ‘oversized’ fit, make sure it’s loose in the correct places. A typical oversized shirt is loose around the shoulders, sits 5 to 6 inches loose around the chest too, and falls down the waist in a straight cut.

Take care of this or simply go for an oversized piece. Your call!

Balance with Slimmer Fit

If you’re not ready to go full on oversized, try adding balance to the look by throwing on a pair of skinny jeans or straight-fit trousers. A la mode but within your comfort zone, I’ve got you sorted mate!

How to Style a Men’s Oversized Shirt

Let’s go through some cool oversized shirt styling inspirations so you can hop on this trend and serve some drool-worthy looks.

Basic Tee FTW

White oversized t-shirt and jeans
Photo by Wirestock

We can never get enough of basic t-shirts, can we? A basic oversized tee is the most effortless recipe to look cool yet comfortable. Slip into a breezy, oversized, basic white tee with a pair of denim pants to create a minimalistic look. Introduce accessories to the equation and you are ready for a casual lunch date.

Spruce up by Tucking-In

Tucked in oversized shirt
Photo by Sam Aronov

Tuck an oversized button-down shirt into a pair of tailored pants if you’re aiming for a dressier silhouette. A tucked-in shirt adds structure around the waist while still being flowy around the shoulders and arms. Go for contrasting colors to accentuate your outfit and make it look like you made effort without actually doing much 😉

Layer Up

Layered oversized shirt
Photo by Andrea A

I love this all-white outfit due to the subtle pop of color introduced via the pale blue oversized shirt. Layering an overshirt on top of a basic vest is an easy bet for anyone who’s reluctant to hop on the oversized shirt trend.

Can’t Go Wrong with a Checkered Shirt

Oversized check shirt and jeans
Photo by Wirestock

An oversized checkered shirt, open cuffs, a few undone buttons, and ripped denim pants is the coolest way to create a rugged handsome look. The chunky shoes add an extra oversized element to the outfit.

Matching Separates

White shirt and pants
Photo by Andrea A

Matching oversized separates is a smart daytime look. Go for a slightly thicker clothing material if you’re aiming for a luxury touch in your outfit. Undo the shirt buttons and toss on a basic vest underneath to deformalize the outfit. Loafers are just the right balance for the casual and formal situation.

Keep it Cool with Shorts

Logo oversized t-shirt
Photo by Andrea A

An oversized shirt paired with frayed shorts is a statement summer outfit and an infallible choice to beat the heat. The yellow graphic on the oversized t-shirt ensures the otherwise entirely white outfit pops.

Go Sleeveless

Sleeveless athletic shirt
Photo by WireStock

An oversized shirt doesn’t give you the edge to flex your muscles. The sleeves fall quite down to the elbows. But an oversized sleeveless shirt with padded shoulders could be the solution. It is the right choice when you’re looking to ditch your run-of-the-mill gym attire.


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