What is the difference between having a personal style that doesn't depend on trends, and just looking out of date?

This totally makes sense, but my issue is that (although this post isn't about my personal style or help for me individually) there are things I love that do NOT look good to other people. I love bandage dresses and always will, but last time I posted one here people commented on it being very dated (and they were right.) In fact, people commented on it being "tryhard" attire. I wish it was true that "if you love something and it brings you joy then it's a good outfit" but that's really not true, at least not in my case. A lot of the time it's also hard to tell if I like something because I really like it, or because advertising/media has made me like it. For example, mom jeans. I hated them when they first came out, now I like them. Do I genuinely like them, or do I just like them because they've slowly started to read "Fashionable young woman" to me instead of "what my mom literally wore in 1992" like they used to?

My outfits, at least I think, have gotten a lot better in the past several months because I haven't focused overwhelmingly on wearing whatever is the most trendy, and I was quite happy with that, but just the other day I got a comment that told me another website makes fun of my outfits consistently because they're "not fashionable." Now, I know I shouldn't care what every single person thinks of me, but there I was, thinking "Okay, I'm wearing what makes me happy, I think I look pretty fashionable" and then I get that news.

/r/femalefashionadvice Thread Parent