Representing the Chi is all well and good, but wearing a generic "Chicago" tee will make people assume you're from Iowa, and didn't have the cash for one of those classy collector's mugs from the O'Hare Hudson News. Show your severely local side with shirts from That's My Stop.
Started by two Lincoln Square brothers with a hardcore public transpo fetish, TMS's 144 different designs shout out every El stop -- including directional coordinates -- on all eight lines (you know it's comprehensive when you see the Skokie Swift). Thoughtfully available in sizes up to XXL, every tee comes in both its El line color and dark gray, with stops on multiple lines coming in all appropriate colors -- for instance, Western (blue, brown, orange, pink) edges out Belmont (red, brown, purple), though Belmont still runs away with the "average time spent avoiding eye contact at this stop" award. Two red-line stops get special treatment: Sox-35th can be had in black, while Addison's also available in blue-line blue -- lighter than Cubbie blue, so if the team slides back out of first, you can just say you're representing the spinach artichoke dip at Casey Moran's.
Soon, TMS'll give El to kiddie tees and onesies, plus adult long-sleevers and hoodies -- so Iowans will assume you're local, and about to jack them for their skyline mug.