9 Modern Ways to Style Oversized T-Shirts for Men

You've got yourself an oversized tee—congrats! You now own one of the most versatile pieces in men's streetwear. But here's the catch—not everyone knows how to style it without looking like they just rolled out of bed. Let’s face it, men’s oversized t-shirts have evolved beyond mere lazy-day pieces. They’re making waves on red carpets, trending on Instagram, and turning your local café into a runway. Whether you’re out on the town, hanging with friends, or dressing for a date, there’s a way to rock that comfy tee and still look fantastic.

​In this guide, we'll delve into how to style an oversized t-shirt and share 9 awesome oversized t-shirt outfit ideas. And no, we’re not just talking about jeans and sneaks. Think beyond clichés—layered looks, edgy styles, and outfits with cool energy.

Underneath a shirt

Nothing says “confident style” quite like a well-layered outfit. If so, why not layer an oversized t-shirt with a shirt? Yes, you read that right. Throwing a checked shirt over your tee—or even tying it around your waist—can add an edgy streetwear-inspired vibe. Whether you’re taking a stroll in the city or going on a casual date, this oversized tee look with chinos or ripped jeans, along with some classic trainers or characterful boots, will help you embody urban chic.

​Les Deux T-shirts are ideal for layering, whether you prefer them loose or fitted. For our oversized tee look, we styled the Crewneck loose-fit t-shirt underneath the Check-pattern overshirt. As for the bottom, you can choose jeans or chinos, depending on where you are headed.

With jeans

We all have our go-to pair of jeans—baggy, slim, bootcut, skinny—no matter which style you prefer, it's important to know which tops pair well with them. When it comes to an oversized t-shirt, your choice of denim can really make or break the outfit. So, which jeans work best with oversized tees? Given that baggy jeans are currently in vogue, you can go either for a looser fit, then choose less structured denim, or choose a sturdier pair to achieve a workwear-inspired look. Try a slightly cropped t-shirt to create a more balanced silhouette, or, if you want to create dimension, pair fitted jeans with a baggy top. Just one tip—better steer clear of super skinny jeans, as the contrast with an oversized tee can be too extreme.

We are gonna team the slightly voluminous Tapered jeans from Les Deux with the Oversize cotton t-shirt from Holzweiler. To enhance the look, finish it with the chunky sneaks à la skateboard aesthetics.

 With cargos

An oversized tee can make a striking statement on its own, but the choice of bottoms plays a role as well. Speaking about trendy outfits for men, a pair of cargo pants is a great choice. These utility trousers come in baggy and slim-fit styles, each with its distinct look. Baggy cargos create a laid-back aesthetic when paired with an oversized t-shirt, without veering into scruffy territory. On the other hand, slimmer-fit cargos bring a sportier vibe, which is ideal for gym sessions or athleisure outfits.

​Check out the T-shirts from Aeronautica Militare if you are a fan of practical yet stylish workwear. Their Embroidered loose fit t-shirt paired with the Loose-fit cargo trousers from A.P.C. makes for a balanced look—like you are about to head to a garage to pick up your freshly tuned BMW but also have some plans in the city center. Feeling the lack of accessories? Les Deux’s Dad cap will fill the gap.

With shorts

The warm season is upon us, which means it’s time for guys to look for lightweight outfits that keep you feeling fresh in the heat. Off to the gym or dressing casually for the day, pairing oversized tees with shorts is a foolproof choice that flatters everyone. We recommend a baggy T-shirt that falls just below your waistband—the shorter cut of the shorts allows you to go longer on top. Hoochie daddy shorts, breezy basketball-style mesh shorts, cargo shorts, long-line denim—they all work equally well. Pull up your socks and team them with your favorite summer trainers, or opt for a comfy pair of sandals if the weather allows.

Let’s combine the Cargo cotton shorts from Moose Knuckles with the Regular fit t-shirt from Les Deux. The graphic print on the back of the tee and the cargo design of the shorts work so well together that they evoke a nostalgic feeling of the 2000s.

As athleisure

Oversized t-shirts for guys are a prominent staple in streetwear; we’ve figured this much out. Men style them with sweatpants, sporty sneakers, and caps for an urban look, with well-placed graphics or subtle logos to capture that understated streetwear vibe. The classic hoodie is another essential in every man's wardrobe, whether you're a yogi, lifter, actor, or athlete. Layer it over a baggy t-shirt for the ultimate in comfort. With extra room around your torso and arms, you'll feel more relaxed, and we all know—the roomier, the better!

​When comfort is your priority, there is nothing finer than T-shirts by Tiger of Sweden, and we layered their Relaxed-fit t-shirt underneath the Hooded zip-up tracksuit set from Aeronautica Militare. To complete the look, try matching sneaks, like the Suede contrast-detail sneakers from Voile Blanche.

With trousers

Want to make an oversized tee feel sharp without losing the ease? Pair it with wide-leg trousers and give it a tuck—yes, a tuck. It shifts the vibe from lazy to intentional in seconds. Add loafers, and—you’re serving something smart, a little subversive, but totally wearable. It’s giving an “I know what I’m doing” look without the need to say it. Unexpected? Well, maybe. But fashion-forward? Yes, sir. Try it once—you’ll feel it click.​

We recommend the Wide-leg wool trousers from Holzweiler and Les Deux’s Cotton t-shirt combo. And don’t forget your smart footwear—Hereu’s Slip-on loafers.

With a suit

How to wear an oversized t-shirt with formalwear? Nobody tells you this, but yes—you can wear an oversized tee with a suit. The trick is to keep it clean—no logos, no loud graphics. Just a soft, oversized tee under a relaxed, unstructured suit—linen if you’re lucky. It tones down the formality without killing the look. Here, the suit feels cool, not corporate, and makes people look twice—in the best way, of course.

The Mercerized relaxed-fit t-shirt from Tiger of Sweden is perfect for such an ensemble—a clean white piece, nothing excessive. Pair it with the linen suit, featuring the Linen blazer and the Linen casual trousers, and you have a fashionable look for anything from garden parties to fine dining.

Over another tee

Up for something unusual—layer a loose t-shirt over a fitted one. Choose a contrasting color or a graphic pattern to add depth, and roll up the sleeves of the top t-shirt to showcase the inner layer. This look is focused on dimension and is perfect for chilly days, as long as you wear a long-sleeved tee underneath. Follow this modern urban vibe through to the end and finish the look with slim-fit jeans or joggers and comfy trainers.

As a first layer, we suggest the white oversized tee, like the Basic cotton t-shirt from Aeronautica Militare. Over it—the Text-printed cotton t-shirt by Dirk Bikkembergs. On the bottom—the Slim-fit jeans from Tiger of Sweden. 

Underneath a jacket

Layering a jacket over your oversized t-shirt is a surefire way to street dressing. Whether you choose a graphic tee or opt for a simple design, a jacket transforms your look. Select the one that fits the vibe of your tee—denim, leather, varsity, bomber, or whatever feels like home. Ditch the buttoning, roll up the sleeves, and let the combo do the talking. 

If the tee is basic, such as the Cotton t-shirt from A.P.C., you can put anything literally on top, for example, the Classic denim jacket from Citizens of Humanity. Minimalist t-shirts give you the freedom to choose any type of outer layer.