I know I've posted on similar topics before, but I don't think I've posted in this particular thread. Oh well, if I have, I guess I'm going to, again! LOL
I've improved in this area over the years. Somewhat. I think. Ok, ok - if I didn't try really, really hard, I'd still be wearing the same thing every day for a week.
In my middle/high school years, I wore whatever I happened to put on in the morning. I had NO understanding of how to match clothes, so ended up with very odd combinations a great deal of the time. I have to assume my parents had given up on ever getting me to understand that striped purple pants just didn't work with a yellow plaid shirt, and the like. I was not allowed to wear the same thing to school twice without it being washed, but would often wear the same set of "play" clothes everyday for a week.
Late teens and twenties, I wore jeans with hard rock and heavy metal band t-shirts. I did a lot of manual labor type work, so wearing a shirt multiple days was pretty much not an option. Jeans, on the other hand, got worn until they looked dirty. I loved it - I always matched, and it took no effort whatsoever, other than deciding whether I wanted to wear Iron Maiden, AC/DC, Deep Purple, Floyd, etc. that day! Usually just grabbed whatever was next in the pile.
In my thirties and forties, I went the route several others have described: 5 pairs of khakis - different colors, but the same style - and a bunch of polo shirts in different colors - all the same brand & style. I was able to wear a "different" outfit everyday without having to think about it, and only had to do laundry every other week!
Now, I have a boyfriend who is very much a fashionista. (Boy, talk about opposites attracting!) I now have a closet full of carefully selected clothes that are comfortable and look great on me. I try to think carefully about what I've worn recently when choosing a shirt (almost always jeans, so that part's easy), but I seem to get stuck in cycles. Like, every shirt for 2 weeks is striped, or they're all some version of paisley, or they're all blue, or something like that. And, at least twice a month, he'll look at me and tell me that I've worn that same shirt 3 or 4 times in the past week - and I didn't even realize I was picking it out again.