I used to keep two fairly wrinkle free outfits at work -- black what-I-call Chico's pants, those travelers pants, a long skirt, two different tops, a black sweater or neutral jacket, a decent bra, and a pair of sandals. In the winter the Chico's pants would work with a layer of Cuddle Duds underneath, and I'd keep a couple of pairs of black tights in a file cabinet drawer, make-up too, and a pair of Danskos or other appropriate shoe under my desk. It was just the underwear that had to make the trip back 'n' forth. After the morning I rode to the Y, swam, then went to change before riding to work and discovered NO UNDIES -- I am now the proud owner of a Pepto-Bismol pink strapless, all that Target had in my size at 8am -- I started keeping an emergency set at the office.
Terry sells this thing they call a bicycle cube for keeping all your stuff together -- plain, deluxe, and recycled deluxe, but I would pack my pannier the night before. I like the checkoff list idea!
And that martini story is the best!
Dress where I work is very casual, so unless I get creamed by paint, playdough, school lunch, or eek! I usually wear the same jeans all week anyway, so it doesn't matter if they spend a few nights in my office file cabinet.
In cases of eek! it might mean a trip home to the laundry immediately.