1. Wear whatever you want.
Several years ago I started to take an interest in fashion, style, and clothing. (I won't lie to you: this is coincidental with my body size changing, and having more options available to me because of it – coupled with my masculine presentation. This is not something that I agree with; it is a systemic problem I'd like to explore another time.) But as I started to get my bearings on what I liked, I found that I couldn't quite trust my own taste and sense of what worked and didn't work for me.
Initially one of my good friends helped me with my wardrobe. She encouraged me to try new things. I trusted her, as she always had a great style about her and still does. She was a style mentor, really. I can't say I did any grand experiments then, but definitely veered towards updating my look without changing it dramatically.
There was one thing I tried shortly afterwards: I picked out and tried on a couple of articles of clothing that I would never, ever wear “ordinarily.” It was like opposite day. For me that meant grey skinny jeans and a big, chunky sweater. I didn't think much of the sweater, but, I was surprised at the skinny jeans and how good they actually looked. This surprised me; I wasn't “supposed” to wear skinny jeans because I was too big for them. While I didn't buy the jeans that day – I wasn't confident enough yet – that moment stuck with me, and started to help me question my assumptions a bit more.
Over time I found a more comfortable place in my wardrobe, a safe place. I was aided by many sites on the web. Several of them offered up “rules” for what men should wear; I found them immensely helpful. But there was an undercurrent that surfaced on several of those sites: there was a certain bro-y angle, and a sameness. Some sites joked about the “uniform” of a blue or white OCBD (Oxford cloth button down) shirt, slim khakis, and Clarks Desert Boots.
Another thing that popped up on said sites was to put down others' sartorial choices from time to time. Worse, I saw myself picking up that attitude. If I saw someone wearing square-toed shoes, for example, I'd be more inclined to think and maybe even say something to a friend about it. Part of the problem here was that I used to wear said square-toed shoes, and once I learned that they were not “okay”, well, I wanted to distance myself from that as much as possible.
The rules, the pointing and laughing at people not following the rules, plus the “here's what you must have in your closet” stuff was ultimately stifling for me. Judging other people's choices? Nah, that's not really me, really. The rules? They weren't expressing who I was, and, I'm privileged enough to be in a position where my clothes can do that.
Late last year, I found an interview with Father John Misty. I don't agree with him on everything, but he did say some smart things about fashion and clothing.
What he can’t stand are “basic-ass dude” clothes. “Like, everyone kind of looks like a graphic designer. I just hate that look.” It’s a trend, he says, that mirrors what’s happening in music. “It’s predicated on not fucking up, as opposed to the emphasis really being on expression. There’s a lot of prescriptive fashion — ‘Oh, you need the perfect white shirt, and you need the perfect khaki’ — and it’s just so boring.”
This nailed it for me. It encapsulated so many of the shortcomings I saw in men's clothes. I looked around, as I had before, and I saw fewer and fewer clothes I truly liked and enjoyed wearing. My closet felt like it came with a web approval, and was fine, but the whole thing was fairly conservative and not really reflective of me.
This year, I've worked to consciously change that. I'm almost certainly wearing things now that are against some rules, or some other shit. I have a lot of bright colors in my wardrobe (could be seen as “too feminine” or “too juvenile” or both). I got real and jettisoned all of the blazers that I was never really going to wear (blazers just didn't take for me – a classic “I should wear them!” moment). I am shifting away from button downs a bit. It's a weird and delightful place to be, because it's experimental and because I'm finding more and more stuff that suits me, now.
It's possible that I needed to go through a phase where I followed the rules of menswear without deviation in order to get where I am now. It might also just be me in my late 30s saying, “Fuck it, I'm just going to wear this.” But in either case, I have walked away from these rules questioning how much good they actually do.
Naturally there are exceptions. When I'm doing a client pitch, I will don something I affectionately call “businessperson cosplay” – because how often do I wear suits and ties, or blazers, just because? I can roll with that. And, if you're starting your very first capital-P Professional Job and have no idea where to start, and need a jacket or a certain skirt length or a blazer or all three, sure. Having a starting point makes total sense.
But rules are meant to be broken.
So if you want to wear square-toed shoes, or denim with denim, or shirt and tie without a jacket, or whatever is deemed uncool this season... go for it. You don't need my permission but, I promise you, I will not judge you.