You've worn tees for years. You know your size. But you're considering an oversized fit because you've seen it on influencers and you like the vibe. Fair enough.

Oversized isn't just "buy two sizes up." That's the rookie mistake. A true oversized tee has a boxy cut, dropped shoulders, and sleeves that end mid-bicep. The hem should hit at your hip or slightly below. If it's just baggy in the body but the shoulders are still regular, it'll look like you're wearing a hand-me-down.

When you do go oversized, everything else in your outfit needs to be more fitted. Skinny jeans or tapered pants, clean sneakers, maybe a cap. The tee is the loose element; you can't pair it with cargo pants and a hoodie or you'll look like a laundry pile.

Also, oversized tees are not ideal for layering under jackets—they bunch up and look messy. If you live in a cold climate and plan to wear a hoodie over your tee, stick with regular fit.