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.