I find this concept very interesting and mystifying. Reading clearlyclaire's interesting post on the 10 item wardrobe and the subsequent comments from several YLFers got me thinking.
I know I probably wouldn't wear exactly the same twice in a row if I were to meet exactly the same people. But I'd wear it in a heartbeat if I had different plans on the two occasions, or would meet a slightly different crowd, i.e. two different classes, but the same coworkers.
My administrator was interviewed on television not long ago, and has used the clip on several occasions in presentations later. She purposely wears the same outfit as in the tv interview, and makes a point about it which makes everyone laugh. I find this amusing, too. She is a stylish, modern classic lady by the way.
Being European, I think we put less emphasis on looking new, or different each day, than Americans. I have noticed that even though we wear similar clothes, we will wear them at different times. Europeans dress more casual for work than for parties, but Americans are the other way around, I think. This is of course broad generalizations.
When will it feel wrong, or intimidating, to you to be seen in the same clothes whiten a very short time frame, and why? I'm all ears!