Karie, I remember the endless variety you conjured from your closet! You also sewed some things, which I think does help a lot...
And Roberta, Jenni -- I'm as hungry for compliments as the next person and enjoy them! But I don't think repeat outfits reduce them, at least not in my world. Keep in mind, though, that it's been a long long time since I worked in an office with the same people every day. When teaching in person I do see some of the same people each day, but not only the same people.
I think people in my life might notice a repeat outfit...but they probably notice more that I am dressed in a way that strikes them as fashionable or very "me." And I become known as "that" person -- the one who always looks like she made some kind of effort. And although neither of you said this outright, I think you, and several others have implied it -- when we take care with our dress, a certain subset of people in our lives will come to expect it of us and appreciate it in us and we'll become known as the "fashionable" ones.
I'm not sure that uniform dressing makes that impossible, though. It just has to be signature uniform dressing, as with my long ago colleague. (I also happen to think this will not work unless the look is intentional and current, but I might be wrong.)
Though I take Isabel's point. To some degree, this is gendered. Harder for women to wear a "uniform" and be considered fashionable. Maybe less so now than back then -- I'm not sure.
People definitely don't notice if you repeat an item, unless they are real fashionistas themselves (in which case, isn't it grand when they notice?) or unless the item is exceptionally distinctive. The same red sweater can be remixed a dozen times without anyone thinking, oh, she's wearing that darn red sweater again. All the more so if we are talking about black pants.
But -- to take a different example -- what about a wild conversational print? Or even a subtle one?