Joy Division

The Shirt: This shirt from the iconic 80s post–punk band Joy Division has gotten more and more famous over the decades. Its striking design has even been (unsuccessfully) appropriated by Disney for Mickey Mouse merchandise. What you think you’re communicating: Wow, I understand music on a level you can't really imagine if you listen to anything after 2000. What you’re actually communicating: I have shopped at Urban Outfitters.

Red Hot Chili Peppers

The Shirt: This is the most well–known of all Red Hot Chili Peppers shirts, emblazoned with the same signature red asterisk–thingy logo that the band has used for decades. You Think: I’m too chill and laid–back. Let’s smoke a bowl sometime and chill out while we listen to uh… that one really good album I can't remember the name of. I'm mad stoned. Actually: The first time I got high was at Jewish summer camp in 9th grade and my counselor was playing "The Zephyr Song.”

Odd Future

The Shirt: While there are numerous shirt designs floating around for this offbeat rap collective, this one is probably the most provocative, which says a lot. It features Odd Future's trademark perversion of religious imagery — which seems to sell a lot of shirts. You Think: I'm so hardcore, I’ve been to an Odd Future concert. Actually: Things got a little rowdy about 10 minutes into the show, so I left and bought this shirt online.

Tupac Shakur

The Shirt: The untimely death of this legendary 90s California rapper has led to the proliferation of tons of oversized black T–shirts branded with his likeness. But wearing them doesn't necessarily increase your swag quotient. You Think: I’m still mourning his death because his music, was like, poetry, man. For the people. Actually: I'm trying way, way too hard in general. But also to show you that I'm a rap connoisseur, which I probably am not.