I have to go with a TOTAL of 50 bucks, from one trip to the strip mall a few weeks ago:
1. Used (well broken-in) Brooks B-17 from the Good Will thrift shop, $4.50 (that was for a whole bike. I took the seat and barcon shifters and donated the rest back).
2. Barcon shifters from the same bike, free.
3. Wool Army "fatigue sweater" (like a Henley-style shirt), $2.
4. Two merino wool long sleeved polo-style shirts, almost dead ringers for my $85 Rivendell wool jersey, $3 each. I'm serious--if you took off the labels and rear pocket, you couldn't tell which was the big-buck bike jersey and which came from the thrift shop.
5. A Specialized Hard Rock mountain bike with Cateye computer and $40 Blackburn rack, $25 (I swapped the tires for some road rubber and put on fenders, and my wife's commuting on it. Didn't even need a derailleur adjustment).
That's, what, $37.50? And I had a great fish taco for lunch for another seven bucks.