Picture yourself walking into a merch store. The regular fit tees are folded neatly on a shelf, the oversized ones hang loose on a rack. Which one catches your eye? If you're buying for someone else, you don't have the luxury of watching them try it on. So you need to rely on what you know about their wardrobe.

Regular fit is the classic T-shirt silhouette: it follows your body's lines without hugging too tight. Oversized fit is a different animal—it's deliberately baggy, with dropped shoulders and extra room through the torso. One isn't automatically better; they just serve different style goals. Your job is to match the tee to the person, not to pick a winner.