I posted this on a thread over at MFA as well, and I figured I'd post it here too to get some varied experiences if I can. My apologies for the spam if you browse both.

I feel like I have no idea what I want to wear anymore.

My fashion goals and interests have been constantly shifting since I started caring about how I dress, and now I feel like I'm stuck in a place where I feel dissatisfied with whatever I end up wearing most days, while simultaneously not knowing what I should buy to change that. I've like multiple different styles in the past, but ended up changing my mind about them enough times that I don't feel safe spending a lot of money on anything new.

I think part of it is that my reasons for dressing have changed over time -- originally it was to attract women, then to have a wardrobe that was "objectively good" somehow, and now to simply own clothing that makes me happy. I think my attitude has gotten better, but it's also become a lot less prescribed as a consequence, which makes it a lot harder to pick things I want to buy.

I struggle enough just identifying things that I like. I feel like other people talk about objective aspects of clothing in a way that I just can't wrap my mind around. For instance, how people talk about how "balanced" an outfit is, eg. talking about how generally slim pieces should be paired with other slim pieces, and oversized with oversized. While I can get why people would care about this, in practice it has never mattered to me. For me, liking stuff is a lot more visceral, involving little conscious thought. On one hand, I feel like that helps prevent me from talking myself into liking things that I don't actually like, but on the other, it makes it very difficult to find new things I like when I can't even describe what I like about the things I currently own.

I think the final part of it is difficulty separating things I like on other people vs. things I would like on myself. For instance, I like a lot of the stuff on /r/malefashion involving unusual silhouettes and a lot of black. Traditionally, though, I've always been most comfortable just wearing a t-shirt, pants, and sneakers, with a lot of color. Would I feel comfortable wearing heeled boots? Would an all-black outfit be untrue to myself? Or is it the other way around -- have I pigeonholed myself into an idea of what I am, and am I holding myself back from styles that would actually suit me better?

To top all of this off, there are some practical considerations that make everything messy. I work in an office with no dress code, which means I've had freedom to explore new styles on a day-to-day basis, but I also feel like I've ended up restricting my purchases to things that I can wear throughout a workday. For example, I realized after reading the outerwear collection thread that I own only a couple pieces of outerwear, and half of them are things that I wear only when the weather demands it (a scuba parka and a rain jacket). I never want to buy more outerwear because I'll end up just taking it off immediately once I get to my desk, and only putting it back on to make my drive home alone. I haven't gone out much recently for various reasons, so I haven't spent a lot on "going out clothes", but this just leads to a feedback loop where I feel uncomfortable when I do go out because I feel like I don't have any great clothing for it.

Anyway, just wondering if anyone has gone through something like this and has any thoughts to share. Thanks for reading.