I'm not a radical simplicity person but I don't like fashion and have a hard time finding clothes that fit me well, so my basic formula is enough solid-color t-shirts and polos and black khakis to last me two weeks. Besides that I have a few special occasion clothes that I rarely wear because I have to dryclean or handwash, and some fannish T-shirts that are excluded from regular rotation because I can't wear them to work, and for me that feels like it's enough.

I think the times I'm most anxious about having enough clothes are the times I feel like I'm being judged on my appearance, or the times I feel like I'm being judged in general and use clothes as a convenient way to deal with the feeling of being judged!

I absolutely don't feel like my semi-rejection of fashion and clothes shopping should be normative for everybody, because for a lot of people fashion is beautiful and useful as self-expression and social signaling. I think the point where it goes overboard is the point where a person treats clothes acquisition as something to do for fun every weekend, or buys clothes without thought for "Am I actually going to wear this, does this fill a gap in my wardrobe, what else do I have that I'll wear with this, am I buying this because I love it or need it or just because I feel like buying clothes?"