The real trade-off between oversized and regular fit for travel isn't just comfort—it's the way the tee behaves after a few hours of wear. Oversized tees tend to wrinkle more, especially in a backpack. Regular fit tees hold their shape better, so you can wear them straight out of the bag for a night out.

Also, think about layering. If you're going to wear a flannel or a light jacket over your tee, a regular fit is easier to layer under. Oversized tees can bunch up under a jacket and look messy.

And here's the thing nobody mentions: oversized tees are great for lounging. On a long flight, you want something loose. But once you land and start moving, that extra fabric can feel like it's in the way. Regular fit is more practical for activities.