A couple years ago, I decided to do something about my 'meh' clothing situation. At the time, I wore nothing of any note... tshirts, fleeces, and cheapo jeans that didn't fit too well. It hasn't been the most ground shaking change, but I've upgraded my wardrobe to a bunch of nice button downs with jeans that fit right, decent outerwear, and a set of nice shoes. Probably just as forgettable as before, but without looking so bad. It's a different kind of uniform. Back when I started refreshing my wardrobe, it was easy to find and pick new pieces that added something new to what I had, pieces that fit what I was trying to do and fit well. Recently, though I've noticed that things aren't that easy any more, and a lot of the things that I get drawn to are functionally duplicates of things I already own. A guy can have too many OCBDs. I feel like I'm slipped back into the same sort of slump, of essentially putting on whatever I see first. I think I've raised the bar, but have hit another plateau. One issue is my profession. I'm a software developer in a large casual office. Most people in my office still wear jeans/tshirts/hoodies on most days, so there's not much pressure to dress better. If I did, I'd probably start to look out of place. This funk has got me thinking that I need to step back, reevaluate my wardrobe and figure out where to go from here... but the problem is that I don't have a good sense of how to do that. I'm hoping someone here can lend any advice about how to do this. I'd love any advice. Thanks.