wearing off-trend stuff without looking dated

Looking at theme waywt made me realize a handful of those outfits are things that, if the pants were switched out for something straighter, I would just unironically wear and feel pretty good about myself in. For example, I've had a pair of black sef harness boots forever, like at least six years. Wearing them with skinny jeans obviously feels like heidi slenderman called and wants his jawns back. But wearing them with cowboy cuts feels...maybe not "on-trend," but "me" in a way I'm pretty happy with. They do what a black cowboy boot would do but with more hardware. They feel true to what I like about my clothes and about me, and I still wear them two or three times a week. I guess the question its prompted is twofold, one practical and the other philosophical: Practical/for me: Is that a reasonable way to engage with clothes (both the specific example and more generally) or is it needlessly holding onto the past? Is my fondness for my edgy little elf boots a fetter on getting a fit off Philosophically: Where/how does the line get drawn between "this isn't hot shit anymore but I like it" and "this looks dated and cringe"? (I have some thoughts about this being a quantitative vs qualitative change thing, but this is unwieldy enough as is) (also I know this straddles the line between questions and discussion, it's here for now because there's an element of "tell me whether it's wack for me to like my shoes" even if it's more a way in to a bigger question)
6 Replies
zeometer
zeometer5mo ago
i think if you like something you should wear it. there's no rules on what to wear as long as you're fully clothed, and if you think the boots are cool and feel good in them, then wear them. ironically enough skinny fits are circling out of trend, but #theme-waywt right now suggests a number of ways to wear them; the unifying factor is being confident in the fit to begin with. the actual fit of the shoes/clothes is a secondary concern; people are less likely to care if you clothes fit well or at least with intention
jibba
jibba5mo ago
I think two main questions you want to ask yourself are 1) what exactly does dated mean to you, and what do you dislike about it? And 2) what about the past do you feel like you might be holding onto? Does it have positive associations? Like Do you feel like you still have interesting things to say with your older clothes? Perhaps neutral: Do you just like how their main aesthetic associations make you feel? Or maybe negative: you want to hold one to your youth?
MobileSuitGrundrisse
This is an interesting way to reframe the question, thank you both! I think this is less a question of rehashing the tired ass conversation about skinny jeans the subreddit used to be subjected to all the time, and more a question about stagnation. When I say "dated," I think coincidentally here I mean stuff that's off-trend. But really, I think I more just mean "things I've been doing for a long time." What I dislike is less, for example, that I've been wearing the same shoes for years, and more that my fondness for them could be discouraging me from experimenting. I like the shoes! I think they're fun! But I worry about the slippage between "this is out of fashion but I think it's fun" and "I am resisting anything new because I'm comfortable." I'm curious how people combat that impulse with pieces they've grown attached to over a long period of time.
jibba
jibba5mo ago
I think this is a lovely question. I think zeroing in on stagnation and the refinement of "dated" to mean what you've been wearing a long time, rather than just "evocative of a certain fashion era" is an important one, too. To get the obvious answer out of the way, which you basically answered in your original question: wearing old clothes in new wardrobe contexts (as well as new social contexts!) can give new meaning to them. Familiarity can breed stagnation, but it can also lead you to understanding your clothes in a way you hadn't earlier. This familiarity isn't only on your part, though. It's also for your "audience", those who might have seen your outfits many times over the years. The establishment of certain expectations for how you dress might allow you to have a more advanced conversation with your clothes that you might not have otherwise, allowing you to subvert expectations in subtle ways. ^This would lead to another big question for me: who do you dress for?
MobileSuitGrundrisse
Thank you for the meditative response on all of this, I think the question of social context and audience is really at the core of why it seems like I've been circling the drain on these questions lately (and why I finally made the jump from lurker to poster!) A few months ago, I went through a complete change in the social context of and audience for my clothes. The fear of stagnation, I think, comes from that realization - becoming suddenly aware that, while I may be "saying" the same thing, I'm saying it to people who will receive it very differently. 2017-2023 MSG had to dress to not be mistaken for a student while on the job to be treated with any amount of dignity, but off the clock lived in a major city that was very open fashion-wise. In my leisure time I had an audience with the same main people for several years, who were receptive to and actively engaged in smaller, more advanced conversations. 2024 MSG is more free to dress "how I want" on the job (which is now full-time), but has moved somewhere where the outer bounds of "how I want" are much closer together, even in my leisure time. The conversation I can have with my clothes is now more of an introduction than a dialogue, and it'll be some time before I'm in a position to be in a dialogue again. I think realizing that has made me ask some harder questions about whether individual pieces are still serving me to introduce the person I am now (who I am otherwise far more excited to be than I have been in a very long time).
zeometer
zeometer5mo ago
the fact that you're even contemplating it is a sign that you're maybe past the "i'm resistant to change" stage reading that i'm kind of in the same boat where i've shifted from dressing for others or for some specific purpose to figuring out how clothes can serve me. by trying to figure out this naturally there's a point where you go "okay does this actually work for me" but i let it happen organically rather than trying to engineer it