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How to wear men's oversized t-shirts: our tips

by Urban Star 27 May 2025

How to wear men's oversize t-shirts? Summer is getting closer and it's time to review your t-shirt rotation on Urbanstaroma.com. If you're looking for the best t-shirts to add to your wardrobe, you're in the right place. Finding the oversize or relaxed-fit t-shirt that best suits your style has never been easier. We at Urbanstaroma, long specialized in contemporary streetwear clothing, are here to help you. Explore five outfit ideas to replicate - from minimal style to sporty to streetwear combinations - and choose the model that best represents you. Before discovering how to wear men's oversize t-shirts, let's first understand what oversize means.

What does oversize fit mean

Let's start with the definition of what oversize means in the world of clothing. As you probably already know, a garment is defined as oversize when it has a loose, comfortable, and relaxed fit. In the specific case of a t-shirt, we can call it oversize when the sleeves and the dropped shoulder cut create a relaxed silhouette. A distinction to make, if we want to be more specific, is between long oversize t-shirts and those with a more squared cut: the former can cover much of the legs, shortening the silhouette, while the latter can visually elongate it. Let's take two examples of different oversize t-shirts: those from Beams Plus and the long-sleeve model from Carhartt WIP.

How to wear men's oversize t-shirts: the casual and minimal look

When we talk about casual clothing, we can't help but think of the jeans and t-shirt combo. So the first step to matching an oversize t-shirt in a casual way is to find a good pair of jeans. Going back to t-shirts, before understanding how to wear them, let's find some models that might suit us. A minimal over t-shirt model we recommend is the one from Regards:  made from very soft organic cotton, this t-shirt is a masterpiece of contemporary minimalism. The slightly high neck adds a refined detail to the relaxed silhouette, while the slightly longer sleeves offer unparalleled freedom of movement. Perfect for building basic looks during spring and summer, this Regards t-shirt is available in a wide range of colors. As for the pants, the game is quite simple: just regular cut jeans or classic chinos to create a casual and minimal look. An alternative to Regards oversize t-shirts? The new entries from Frizmworks or the classics from Carhartt WIP.

How to wear men's oversized t-shirts: the streetwear look

Let's move on to our favorite category: streetwear. Diving into new trends can be not so simple in the contemporary street style scene. If you're looking for something recognizable, the t-shirts from Stone Island  can be a great style ally. Among the models to consider are definitely the cotton jersey versions with the iconic Compass logo. Looking for something bolder and more conceptual? In this case, we suggest focusing on MM6 Maison Margiela. From models embellished with the unmistakable Numeric logo to the boldest graphics, MM6 Maison Margiela t-shirts on Urbanstaroma are the true streetwear addict's picks. But how to match these men's oversized t-shirts? We suggest pairing them with a pair of dark jeans with a relaxed fit like these from MM6 or, alternatively, a pair of balloon pants like those from the Korean brand Frizmworks. Complete the look with a pair of sneakers featuring contemporary technology, like the models from Asics.

How to wear oversized men's t-shirts: the sporty look

Let's move instead to another front, that of sportswear. When it comes to understanding how to style an oversized men's sports t-shirt, the tightly woven model from Mizuno  is definitely a great starting point. Made from a cotton and synthetic fiber blend, this tightly woven t-shirt features a silky finish texture and quick-dry technology. Functional details, such as the chest pocket and adjustable drawstring, provide all-day comfort and allow you to adjust the silhouette. To complete the look, you can opt for beige nylon cargo shorts for a total Mizuno look and Salomon sneakers. The alternative? The new arrivals from adidas Adizero SL.

How to wear men's oversize t-shirts: the Japanese streetwear look

Now we come to one of our favorite categories: Japanese streetwear. We're talking about garments that stand out not only for their particular attention to design techniques but also for their premium quality. Among the brands we recommend and consider unique in their design are definitely Undercover and Human Made. How to wear an oversize Undercover t-shirt? Simply with a total Undercover look if you want to stay true to Jun Takahashi's aesthetic. Alternatively, staying on the theme of Japanese brands, you could pair it with a pair of relaxed jeans from Uniform Experiment or a pair of twill pants from Beams Plus. As for the  oversize t-shirts from Human Made, why not go for the brand's most iconic models directed by NIGO? From bold graphics to the Dry Alls or Future is in the Past writings, Human Made t-shirts elevate any look thanks to their careful and distinctive design. To complete the look, we suggest focusing on contemporary sneaker models - maybe a limited edition - like the Converse Chuck 70 2 in 1 x Feng Chen Wang. They are inspired by  Jian Ware ceramics. Need we say more?

Once you understand what the oversize style is and figure out which of the different styles aligns best with you - from sporty to minimal to contemporary streetwear - you're all set. Check out our release section on Urbanstaroma.com to stay updated on the most exclusive drops and streetwear news you can't miss.

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