I am beginning to suspect that it is surprisingly common for intelligent, competent adults to somehow make it through the world for a few decades while missing some ordinary skill, like mailing a physical letter, folding a fitted sheet, depositing a check, or reading a bus schedule. Since these tasks are often presented atomically - or, worse, embedded implicitly into other instructions - and it is often possible to get around the need for them, this ignorance is not self-correcting. One can Google "how to deposit a check" and similar phrases, but the sorts of instructions that crop up are often misleading, rely on entangled and potentially similarly-deficient knowledge to be understandable, or are not so much instructions as they are tips and tricks and warnings for people who already know the basic procedure. Asking other people is more effective because they can respond to requests for clarification (and physically pointing at stuff is useful too), but embarrassing, since lacking these skills as an adult is stigmatized. (They are rarely even considered skills by people who have had them for a while.)
This seems like a bad situation. And - if I am correct and gaps like these are common - then it is something of a collective action problem to handle gap-filling without undue social drama. Supposedly, we're good at collective action problems, us rationalists, right? So I propose a thread for the purpose here, with the stipulation that all replies to gap announcements are to be constructive attempts at conveying the relevant procedural knowledge. No asking "how did you manage to be X years old without knowing that?" - if the gap-haver wishes to volunteer the information, that is fine, but asking is to be considered poor form.
(And yes, I have one. It's this: how in the world do people go about the supposedly atomic action of investing in the stock market? Here I am, sitting at my computer, and suppose I want a share of Apple - there isn't a button that says "Buy Our Stock" on their website. There goes my one idea. Where do I go and what do I do there?)
I've thought about our disagreement, and I think there are several important points.
First, at the risk of sounding vain, it is possible that I'm biased because I'm handsome enough that I didn't have problems attracting attention even in the most misguided years of my youth. (My problem was that I'd usually be oblivious to indications of interest, or I'd sabotage myself by responding to them in naive and clumsy ways, not that I was invisible to girls.) It is possible that for less handsome men, being invisible in the crowd is a big enough obstacle that trying to break it by peacocking is a better option than I'd think.
Then, it also depends on what exactly your goal is. If you're striving to become a full-blown player -- which I never did, both because I was already a bit too old to start working on it when I realized that it's actually a feasible goal, and also because it doesn't suit me temperamentally -- then I suppose more extreme options like heavy peacocking become the order of the day. For less adventurous goals, however, I still think that working on a strong and solid "normal" image is overall a better option for most men.
I've already pointed out that if your face or head shape is not very handsome, you can significantly improve your looks with a suitably shaped haircut. But if you already look handsome with a buzz cut, there are rapidly diminishing returns to what you can do with your hair, if we consider it in terms of handsomeness rather than peacocking. (I hope it's clear what I mean by that distinction.)
Regarding various subcultural styles, I'll reply in a separate comment.
Otherwise, I agree that our age is probably too restrictive in what passes for mainstream respectable men's fashion, and has in fact been ever since the early-to-mid 19th century. I find the 18th century aristocratic men's fashion very appealing, and the 17th century Cavalier style even more.