…I would so try to “Win a Date with Threadless.com“. $250 is nice, round-trip airfare and hotel for a friend and I is nicer, and dinner with Craig and Ross is HOTTT. All you need to do is write an essay (250 words or less) explaining why you love Threadless – can it get any easier? Winners get roundtrip airfare for themselves and a friend to Chicago, 2 nights at the W, dinner at Ballo, and $250 spending money. But hurry up, the contest ends February 3rd.

As a disclosure, I have gushed about Threadless in the past and totally heart them. Also, my sister works there.