If this is your first graphic tee purchase for travel, start with a regular fit. Why? Because it's the safest bet. It works for almost any situation—walking around the city, sitting in an air-conditioned café, even a casual dinner. You won't have to think about whether the oversized tee is going to look sloppy in that photo you're going to post.

Regular fit also packs down smaller. You can roll it tight and stuff it into a corner of your bag. Oversized tees take up more space, and if you're trying to travel light, that's a real downside.

But here's the thing: if you're going to a beach town where everyone's in board shorts and loose shirts, an oversized tee just feels right. It catches the breeze, it doesn't cling when you start to sweat, and it gives you that laid-back travel vibe.