All the Ways You Can Style Oversized Men's Shirts

Oversized men's shirts can be dapper, too, you know.

Oversized men's shirts have found a place in society after we all learned to slack off in style during the pandemic. From the skater-streetwear hybrids to haute couture, men's big shirts have been designed to provoke and reflect the energy of the times.

They can sometimes feel like a throwback, too, playing with our nostalgia for '80s and '90s pop culture. Exaggerated proportions and comfortable fits, after all, have been a focus for various brands over the past few years. And this trend was only heightened by our work-from-home personas.

Of course, styling them can be a challenge depending on your body type and pairings. The bigger they are, the harder they fall, right? So here's a quick guide to oversized men's shirts fashion for you. Let loose, folks.

With Flannel Shirts


Layering is everything when it comes to oversized shirts in men's fashion. And those checkered polos that you have lying around can be the perfect complement to your getup if you're going for something urban and casual. Wear some straight-cut or skinny jeans and a reliable pair of sneakers to complete the fit, and you're ready to head out. This is the kind of outfit you put on when you're meeting some friends over coffee in the morning or in the afternoon. It's more of a daytime vibe, really.


With Denim and Jackets


Oversized men's shirts underneath denim, bomber, and leather jackets is a go-to look for many of us. It creates a great blend of textures and mismatched proportions that way. For your bottoms, you can keep it light and simple with ankle-length chinos and some cool white sneakers. This one, you can go ahead and wear on a night out, nothing crazy. If you're going to a more formal event, you can just tuck your shirt in.

With Stripes

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Rocking men's big shirts are an art form. Because they're a little more on the boxy side, they should be complemented with patterns that take off some of those edges. Stripey bottoms can do just that with your solid-toned oversized men's shirts. Feel free to toy around with patterns and colors. Go as bold as you can with this look. It is, after all, kind of a statement piece. If your trousers are on the looser side, you can opt for a plain big shirt for a chic look. For those of you who want a tailored feel, try a slim-fit one, and just fold your trousers at its hem.


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With Dress Pants


There's nothing that good, old-fashioned dress pants can't fix. They're as reliable as they come. So when you're trying to rock your oversized men's shirts with a pair of your own, you only need to tuck it in and you're set. Make sure to choose a good belt for this one. Try something with a little more texture. Throw on some loafers (high-platform ones would definitely be a vibe) and some colorful dress socks, too. You can definitely wear this to the office or even a small gathering with friends and family.


With Shorts and Crew Socks


Oversized shirts in men's fashion extends to athleisure, as well. This is the kind of thing that you put on when you're fresh from a workout. Nevertheless, it's a pretty easy fit to pull off. Simply grab some decent sweatshorts and some mid-length crew socks and that's about it. You can put on a dad hat and some sunglasses, too, if you prefer.

With Oversized Everything


Why not just go crazy and pair your men's big shirts with some puffy cargo pants or baggy trousers? It's sort of a homage to the '90s in many ways, actually. Don't forget about the sneakers here. You can either go with some nice running shoes, preferrably on the bulkier side. These looks you can wear just about anywhere and at any occassion. Trust us, you're going to look cool no matter what.

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About The Author
Bryle B. Suralta
Assistant Section Editor
Bryle B. Suralta is the assistant section editor of Esquire Philippines.
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