Dressed Down at Threadless

Beneath more than 200 T-shirts hanging from the rafters of shirtmaker Threadless’s cavernous Chicago headquarters, workers play Ping-Pong, billiards, foosball, or Big Buck Hunter. Chief Executive Officer Tom Ryan’s French bulldog Lola, wearing perhaps the only collar on the premises, roams freely. “We believe in having a fun space,” Ryan says.

Employees in shorts and flip-flops toil in sun-splashed bullpens decorated with disco balls, mafia-film quotes (“Do I have your loyalty?”), a seven-foot-tall desk lamp, and a mural of dollar signs floating through an azure sky. The marketing group won a recent office design contest with paintings done by a team member, including one of George Washington entangled with an octopus. “That took the cake,” Ryan says.