Most men’s wardrobes have too many plain t-shirts and not enough interesting ones. That’s not an accusation, it’s just what happens when you default to safe. The problem with personality tees is that the bad ones are really bad. Slogans that read as try-hard, graphics that look like they belong on a stall at a festival, fits that suggest no one involved has ever worn a t-shirt in their life. We’ve done the sorting so you don’t have to. What we’re looking for is the same thing every time: a graphic or design that says something without shouting, a fit that works tucked or untucked, and fabric that doesn’t collapse after three washes. These are t-shirts with a point of view that doesn’t require an explanation. The kind a stranger might compliment you on and actually mean it. Worn well, a great personality tee does more for an outfit than people give it credit for.