I haven’t had a reason to dress up in over three years. The last time I dressed up for an event, it was when I was Best Man in a wedding, back in 2019, before coming out to anyone, back when I was still living under the gender identity I was assigned at birth, in a time that seems almost unreal at this point. Not because I’ve come out in a big way (I’m masculine-presenting for one thing, so not much has changed so far as it feels from day-to-day especially given that I’m also not out at work yet), but because it happened before the pandemic. I almost went to a Roaring Twenties themed New Year’s Even party back in 2019/2020, which would have meant wearing a suit, but I wound up skipping that to stay at home and hang out with my roommates. We played D&D as I pushed them to see how far they could get through one of the starter kit adventures in a single evening. It was a lot of fun, but I kind of regret missing what felt, for a long time, like my last chance to get fancy before becoming the isolated, comfort-focused individual I am today.

I have another wedding coming up, this one as a Person of Honor to someone I consider a brother, so my days of being free of fancy dress were going to end eventually. Instead of waiting that long, though, I thought I’d dress up a bit for a job interview I’ve got with my current employer. I threw my hat into the ring for a job opening that is still mostly with my team but in a new capacity. The idea is pretty exciting and would hopefully address some of the less pleasant parts of my current job (plus, there’s nothing like doing something entirely new and different to at least change the flavor of your burnout), but it would mean changing my standard of dress from pants/shorts and t-shirts to slacks and casual-adjacent wear. Polos and button-downs and whatnot. According to the costume designer at my college, who I went to for advice when it came to creating a more professional wardrobe for myself after graduation almost a decade ago, I’m one of those people who can look good in an un-tucked polo (which I feel is very much a barrel-chested, broad-shouldered body-type thing), so I’ve got quite a range (this is sarcasm).

Still, as I think about what a more business-casual me would look like, I’m running into the fact that I haven’t updated my wardrobe in over three years and I haven’t even thought about what I want to wear and look like now that I’m not restricting myself to the “masculine casual standard” I’ve defaulted to over the years. I honestly don’t even know where to begin exploring anything else and the idea is giving me a great deal of anxiety. I’ve been putting off this side of developing my identity because the last few years have been incredibly rough and I don’t really have the emotional capacity to do an entire fashion overhaul on a conceptual level, much less actually buying and wearing new types of clothes that make me feel more like myself rather than the default settings version of myself I’ve been for three decades. Especially considering that I don’t really know what that would even look like. All I know is nothing I’ve got to wear for the interview feels right.

Part of that might be because most of those clothes don’t fit anymore in ways that feel kind of humiliating. Some of it feels nice, like the fact that some of the shirts don’t fit because my neck, shoulders, and chest are too big thanks to the year of working out I’ve done. Some of it feels truly awful because I know I used to be able to fit into those pants and now I can’t even pull them all the way up. Sure, some of it is because I’ve been doing a lot of exercise cycling, so my calves and thighs have gotten bigger, but even that doesn’t feel great. I’m definitely in better shape that I’ve been since maybe college, but I still don’t feel good about myself and my body. I have worked out for an average of 4-5 days a week for over an entire year and I still feel like almost nothing has changed. I know that’s incredibly false, but it still feels true enough that telling myself that I know better isn’t providing any comfort.

As I try to sort through all of these feelings brought up by the idea of dressing up, I’m really not sure what to do with them. There’s so many different aspects to this, so many different angles to consider, and I’m just not sure what to do with them other than consider them. I don’t really know what to think. I am still working out how to feel about any of this stuff after denying myself the chance to explore this for almost thirty years. It’s a long and difficult journey, it would seen, and it looks like I’ll have to cope with some uncomfortable feelings as I occasionally have to wrap myself in some (physically and emotionally) ill-fitting clothes.