7 Best Oversized T-Shirts For a Streetwear Look

Fashion is cyclical. We experienced the oversized trend in the early 2000’s, than quickly sped through a decade of nothing but skinny and slim fit and now oversized is back and with a vengeance. Especially with the rise of vintage inspired looks and streetstyle, oversized t-shirts are an essential part of fashion in 2022. They are a way to express yourself, your style and your personality.

It’s not just a fashion statement though – it’s comfortable too. Oversized tee’s give off a nonchalant chill vibe that is reminiscent of simpler times. It wears and feels like a cool summer day where you’re chilling with friends and skating by the board walk. Nothing beats it.

What Makes a Good Oversized T-Shirt?

A good oversized t-shirt fits in a way that looks intentional and not sloppy. What does this mean? Well picture this. When you wear a regular t-shirt but simply size up, you won’t get the look you want. Because a regular shirt is not actually cut to be oversized (no sloping shoulders, baggier sleeves that end closer by the elbows and a boxy fit).

A good oversized t-shirt is made in a way to intentionally look oversized with the way it’s cut and designed.

What to Wear with an Oversized T-Shirt?

Oversized t-shirts look best in a streetwear or vintage inspired outfit. Both of these categories are pretty large and encompass a lot of different styles so you will never run out of ways to style an oversized t-shirt.

Some of my favorite ways to style this type of shirt is with the following:

  • Baggy pants: pairing an oversized tee and baggy pants just fits together perfectly. Especially if you opt for workwear pants like Carhartts or a pair of loose fitting cargo pants.
  • Light wash straight leg jeans: again you don’t really want to go too slit on the bottoms when wearing a baggy shirt. A lightweight pair of straight leg jeans give an unrivaled vintage vibe.
  • Jewelry and tattoos: retro watches, rings and bracelets just stand out more when you’re wearing an oversized tee. If you have tattoos on your arm for some reason they just look cooler when paired with this type of shirt.

Best Oversized T-Shirts

Best Value Oversized T-Shirt
Uniqlo Oversized T-Shirt

If you're looking for a staple oversized t-shirt that doesn't shrink and is the perfect weight, we've got you covered. Made from Uniqlo’s innovative AIRism line, this t-shirt is made to be breathable and lightweight. It is also a cotton and polyester blend.

Oversized White Graphic T-Shirt
Zara Oversized Graphic T-Shirt

Youthful, sporty, and effortlessly cool. Zara’s high-quality oversized tee is the perfect layer for our cool summer. Made from soft cotton, it's both comfortable and easy to wear. The fun print on the front just makes it even better. Pair it with jeans and sneakers for a casual look.

Most Color Variety
Cos Blank Oversized T-Shirt

Relaxed, roomy & comfortable. This casual T-shirt is made from lightweight cotton for an effortless wear. It has a flattering cut that sits loosely on the body with long arms and a slightly dropped neckline to ensure ultimate comfort.

Heavyweight Fabric
Rue Porter - Premium Oversized Tee

This premium oversized tee is the perfect fit for your life. Made with heavyweight fabric for ultimate comfort and soft premium texture, you'll never want to take it off. The mock neck collar is stylish and practical for any occasion. Plus, it's untagged.

Best Basic Oversized T-Shirt
Closed - Relaxed T-Shirt

When it comes to your wardrobe, you want nothing but the best. And what could be better than a Relaxed T-shirt made of organic slub jersey? With a variety of colors to choose from, this is a signature style relaxed fit tee that features a ribbed round neckline, and an embroidered logo,

Best Vintage Oversized T-Shirt
90s Vintage Oversized Graphic T-Shirt

Go back in time with a classic! 90s Vintage T-Shirt features an oversized fit, cool graphic, and bold streetwear style. This cool T-Shirt is perfect to round out your vintage look.

Best Streetwear Oversized T-Shirt
Los Angeles Oversized T-Shirt

This Los Angeles-lettered oversized t-shirt is the perfect addition to any streetwear wardrobe. It comes in a variety of colors and the sizing can be extremely oversized which is why even though it's described as for women, any guy can order this shirt for an oversized street style look.