Mark Zuckerberg, CEO of Facebook, recently posted a picture of his closet/wardrobe. This picture had all of the same grey/dark grey T-shirts on the left, and his hoodies on the right. He posted this picture on Facebook with a question of what he should wear. It was sarcasm, but I see value in wearing the same thing every day.
I've considered wearing the same thing every day, and I think ultimately it would be worth it, I personally would run into two major road bumps.
1. Finding the right clothing that feels good. If I'm buying 5 of the same shirts/jeans/pants, I would want them to feel good. I have some clothes I like wearing more than others, because they feel/fit better. If I buy a set of 5 shirts, and 1 of them is uncomfortable, then they're all going to be uncomfortable.
2. Storing my current clothes. I don't think I'd get rid of all my clothes if I switched over to wearing the same thing every day. I would keep some things, which result in storage space. Storing things that aren't used that often might be deemed as wasteful, and doesn't fit in as being a "minimalist".
It'd be nice to know what I'm wearing every day. I don't spend a ton of time planning what I wear now, but even the little time I do spend, I'd like to have that additional time in the morning to drink coffee and eat my honey nut cheerios.
Maybe I'll call Mark Zuckerberg and ask him where he gets his shirts from and have him order a few extra for me. :)