David R. MacIver's Blog

Dressing like you mean it

My attempt at daily posting immediately failed by two days where I was both very low-function and also working from home, in a way that sortof derailed the habit. Oh well, back on the horse.¹

Something weird has started happening to me recently: Chuggers² have started complimenting me on my clothing.

This is, obviously, a tactic. I’m aware that it’s a tactic, and it doesn’t work for getting me to talk with them, but in keeping with the traditional meme about men being complemented on their appearance, naturally they stick in my mind.

Compliments I have gotten:

• “That is a great hat! Are you from the outback?”³
• “You sir, are the sharpest dressed man I’ve seen all day!”⁴

I don’t take these compliments at face value given that they’re clearly coming from someone who wants something from me, but I don’t think they’re necessarily wrong. I’ve definitely been trying to dress better recently, and I think I’ve been succeeding.

Partly this is a function of having lost some weight, which means all the collared shirts I used to wear now fit me again, which is a delight. Partly I just got frustrated and started thinking about male fashion. It also helps that we’re coming into winter, and it’s much easier to dress sharp in winter. I have a great winter coat,⁵ and it’s recently got cold enough to add a scarf, which is another way to add a little bit of colour. In summer, it’s hard to dresh sharp, because you sortof just melt around the edges. I haven’t figured out my summer wardrobe yet, but I’m starting to think about loose linen trousers.⁶

The way I’ve historically dressed has been very default conventional male, slightly better use of colour than average but not much. I’m somewhat hampered by some aesthetic allergies I have, but I think I do OK within that. But dear god is it boring, and I’ve been trying to do better recently. I haven’t made a lot of changes so far really. I’ve switched back to my collared shirts⁷ and added a hat, but apparently that’s already enough to put me in the 99%-ile for male fashion.

I think that’s bad.

One of my touchstones for how I think about skill is Dan Luu’s “95% isn’t that good”, in which he argues that 95%-ile in skill is what you should expect to get to when you actually try to succeed. I think for male fashion, at least in the parts of London and my commute into it I frequent, it’s probably closer to 99%. This probably makes sense - fashion is something you’re forced to participate in whether you like it or not, and that seems like the reference class is going to include a lot of people who aren’t going to try compared to e.g. chess, or Call of Duty, where you don’t even get measured unless you’re at least a bit interested in the game.⁸

Anyway, I think the reason why the chuggers are commenting on my clothing isn’t that I’m dressing well, it’s that they can tell that I’m trying to. This, presumably, means that I care about this, which means it’s a good thing to compliment. It’s a classic piece of advice on complimenting people: Compliment something that looks like they’ve put effort into, not something that is a natural quality of them or that they appear not to care about.⁹ This makes it a good way to grab my attention.¹⁰

On the other hand, one compliment I got recently that I do believe and appreciate is that I met a friend in person for the first time, and he commented multiple times on how well dressed I was. “Like a highly respected academic”.¹¹ Partly this is because we’ve only seen eachother on video calls before, usually on a Saturday morning, which is not generally when I am at my best dressed, so I think my turning up in my classy winter coat and a well-tailored pink linen collared shirt was a bit of a surprise.

As part of the experiment in dressing better, I and various others have been posting selfies¹² to discord, and complimenting eachother in highly specific ways about how good they look.¹³ I’ve really appreciated that, and it makes it much easier to make deliberate decisions, because it feels like you’re no longer navigating blind.

It’s not the only reason, but I do think that one of the reasons why male fashion is quite as bleak as it is at the moment is a relative scarcity of this sort of feedback. It feels great to receive, but also it gives people permission to care about the problem, which I think is a good antidote to a sort of learned helplessness. It feels common when I talk to other men that they would like to care about this but are somewhat blocked off from doing so. I’m sure a lot of that is that is selection bias for the sort of men I hang out with, but that’s fine. If you’re reading this you probably have similar selection biases.

I’ve previously talked about the value of community in maintaining interests. This seems like something that we, as men, should be in community about and mostly aren’t.¹⁴

One particular hook that I suspect is really useful is to not frame it as compliments, but instead asking for advice or help. Men love helping people solve their practical problems.¹⁵ For example, a coworker of mine dresses quite distinctively. His look is not one that would work for me, but it’s a good look on him, and involves a lot of choices that I really never see in the shops. I mentioned this to him and asked him where he shopped and how he found those places. It wasn’t directly helpful, but it did somewhat unblock me in my attempts at clothes shopping, and started a good conversation.

This reminds me. I’ve got a coworker whose glasses I really like, and I’m very in need of new glasses.¹⁶ I should ask him where he got his.