What’s So Cool About Cool?

Is it worth even wondering about what “cool” means?

“Cool” is such a weird word. That’s probably because it means different things to different people, being formed not only by their personal relationship to the object but also to the community around said cool thing. For example, something you think is cool may not be shared by someone else; sometimes a cool thing may be less cool due to the people who also think that thing is cool. Again, that may not be the case for everyone, but I’m sure we think about all these variables in some way or another.

We returned to the idea of “cool” and discussed it on the podcast, which you can listen to below. It’s less about attitude and overt aesthetics but more about the philosophy behind why we think something is cool, especially in terms of this menswear hobby and community. Dive in before reading further!

Podcast Outline

08:12 – Topic Start/Rule of Cool
24:05 – Effort
28:10 – What Makes Things (in Menswear) Cool
40:29 – Mainstream Cool
42:56 – Does it Have to be Cool to Other People/Details and Inspiration
1:00:19 – You Gotta Think You’re Cool
1:02:38 – Are Things Still Cool?
1:10:54 – Wrap-Up

As you can probably surmise from this weird blog, I’ve had a weird relationship with “cool”. I’ve discussed the Rule of Cool before, which focuses more on the aesthetic attitude about dressing cool, but recently I’ve been dwelling on the reasoning behind that. The gut feeling of why we like something and consider it cool, especially in regards to its use in a hobby and by extension, communities. While I do know that it plays with both insular and macro groups, the word “cool” was always something personal to me. In my mind, the word is used to describe something as being more than good. Something empowering, with both an edge and smoothness. A cool thing (or person) is effortless while very clearly dynamic and perhaps multifaceted. Cool is not shallow but personal, introspective, and exciting.

I realize that’s quite a loaded definition for such a succinct word, but hey, I’m working backwards here! I know that I use words in a weird way, pompously creating my own vocabulary like with tailoring (apparently the correct term is “tailored clothing”), stuffy/slouchy, and taste. In short, “cool” is something I reserve for things I like, even if I’m aware that others, whether in my insular communities or the macro/mainstream world, may not see it the way I do. I’m perfectly aware that my stock in what’s cool pales in comparison to any of the greater communities around me. For a non-menswear example, I may be heavily into film score and frequently visit sites that discuss them, but film score is definitely not a mainstream interest in the wider world of music.

What this comes down to, as we’ve discussed in the podcast, is what we like, how we like it (or execute on it), and what affects why we like such things. We’re definitely diving in too deep on this, but it seems there’s more to the conversation about “cool” than the Rule of Cool which like many things we’ve talked about, is a completely subjective thing that is dependent on context and community.

This is especially true in men’s clothing, a bigger world than the niche’s niche of classic menswear that we’re in. For example, slim fit suits are cool in a mainstream sense. However, this look that defines 2010s #menswear, as well as some (now dated) influencers on the IG explore page, may still invoke feelings of empowerment and even aloofness (to tie it back to how I see the word cool), especially suits have lost their lingua franca status and as a result, still stand out regardless of the specific subgenre of menswear you position yourself in. But regardless of how popular something is, I still may not think its cool— I still have my own taste to take into account

In my mind, the way “cool” is tied to the mainstream makes its use as a mirror to the current zeitgeist or trends. It’s again, quite different than my “personal cool”. Perhaps “mainstream cool” when tied to how in tune something is to what’s popular and current is a bastardization of its original usage (and perhaps indicative of how much popular American culture was built by black culture and how its currently twisted). It becomes a form of currency, tied to aspirational status rather than the empowerment provided by a piece of clothing or interest in a hobby (passions themselves can be cool). I’m sure to some (who I’m probably strawman-ning at this point), cool has become the intended purpose of most things and if something isn’t cool, there’s no point in it.

The funny thing is that I partially agree with that last part, especially when it comes to menswear. However, I approach it from a different point of view. Things I wear should be cool, but they should be cool to me.

Thanks to my weird interests, I’ve never thought of myself as cool— but to be clear, I firmly believe that things I like are cool. I’ve said it many times but if you are concerned with clothes that are cool in a mainstream sense and to be free from the “weirdness” or “risk”, everything I talk about probably isn’t for you. The menswear trauma of being called dapper is not a big deal, but if I was concerned with it, I’m sure it would help if I picked the plenty of “cooler” options in tailoring instead of the spearpoint collars, long jackets/big pants, and bold vintage ties that I like. Again, if I was concerned with dressing “cool” in the mainstream sense (or to at least avoid any “cringe” connotations), I should dress completely different than how I do.

However, I think those things (spearpoints, big pants, etc) are cool. Not because they’re different than what’s in GQ or other big menswear media, but because of well…you can read those articles. They just excite me! They are more than good. They are cool and I feel cool when I wear them, even if other people may not agree. I want my wardrobe to be full of things that meet my own metric of “coolness”.

I’m not even sure I can accurately describe why I think something is cool. Is it the historical roots? Possibly. Is it the design details? Definitely. Then come the harder questions. Is it because it’s not popular? Maybe. Would it still be cool if other people were into it? Yes!

That last part is quite interesting as I’ve come to realize that quite a few of the things I’ve liked have been picked up by the many others, not just in classic menswear/#menswear but to the greater men’s fashion world. White socks. Longer collars. Bigger pants. Loafers. Navy Blazers. The Great Menswear Merger and the Post-Pandemic Look have blurred the lines between the niche and the mainstream, especially when it comes to the things that have sort of defined what I talk about this blog. I honestly never would’ve thought I would’ve seen Tiktokers talking about white socks with loafers, high waists, or vintage WWII pants.

I’m not going to lie— the fact that facets of what I’m into have shown up in places that are not just Spencer and me makes us feel pretty good, almost like proof that we have some form of taste that the mainstream can appreciate. However we know that things are always fleeting; we liked Americana and westernwear before and we will continue to like it after it has passed (and its definitely passing). After all, we’ve done plenty of discussions on how we vet trends and see which ones actually apply to us on a personal level (and therefore have staying power in our wardorbes). Perhaps that’s because we don’t have money (or the bandwidth) to buy something just to wear for a little while and then pass it on; we prefer to archive and then get excited all over again when we take them back out.

As much as I like to say that there is a difference between mainstream cool and personal cool, I’m also aware that I am still affected by other people, some of whom are considered quite cool to a variety of people, not just a select few. But to take it back to my original thesis, I think that this is still quite tied to personal cool, as in I see a connective tissue there in terms of interest and vibe rather than simply wanting to wear the clothes they have on. Something about authenticity as well as personal POV and the characters we are. There is still a risk as well, because despite the presence of a few big players in the menswear space, the whole aspect of “menswear being cool” still pales in comparison to the wider fashion world where suits are not the way to go.

I do think that coolness can fade and change overtime, but I think it’s a positive when its on a personal level and tied to a journey rather than simply basing it off of other people’s attitudes. I think its odd when coolness is tied to mainstream enjoyment of a thing, especially when it means that you enjoy it less and may even move away from it. . And even then, because coolness is (or rather should be) a personal metric, execution of coolness will always be different. That’s why it doesn’t matter if someone else gets into white socks and loafers; even if that one aspect is similar, the rest of the fit may not be! However, this may be because no one has ever decided to dress exactly like me.

My attitude is that if more people like something, that’s a good thing! It not only provides camaraderie (fandom anyone?), but it also brings with it multiple points of view aka inspiration. For example, it’s great that I no longer have to look at Esquire Man or old photos; other people can bring in ideas of Golden Era style that inspire me. Those people are cool because I think they are. It doesn’t matter what others think of them, whether it means they don’t like or they do; it doesn’t stop me from thinking something is cool!

Authenticity even makes things muddy, as sometimes the conversation about cool focuses on perceived gravitas and time invested over aesthetically cool things (by which I mean design and curation). For example, there is definitely a subset of people who think that old guys wearing polyester suits and plastic shoes are more cool than ivy clothing simply because the old guys have been dressing for a while and there is an implied gravitas and authenticity behind it, at least compared to a social media driven way of dressing. It’s almost like people use cool simply to be subversive which I honestly can’t knock since details and clothing I think are cool are definitely not as mainstream as other things. Plus, as the Esquire Man showed, it’s not about brand names but about personal taste in the details of the outfits. What’s cool is about how you do a brown checked jacket and a foulard tie; it doesn’t have to be Drake’s, Ring, or even vintage ivy.

And at the end of the day, I am perfectly fine if people don’t dress like me. In fact, I’m still not sure people get how I dress but that’s okay! It would be nice if there was a bit more out there outside of my immediate friendgroup, but it’s not something I’m interested in truly pursuing, at least for mainstream or “cool” recognition (plus not even my friends dress exactly like me). If there is evangelism, its usually for people who are already similar to me and are already into it in some way. More on Menswear Evangelism in the future!

As I finish this essay, I think that focusing on “coolness”, especially with clothing, is a fools errand. It’s such a muddy and relative term that I definitely think that people get lost in focusing on it. I mean, I just did that very thing! The very presence of the levels of mainstream appreciation vs niche is convoluted that I think takes away from the instinctual, gut, and vibe-y feeling of the word. Because again, a garment I may think is cool may be shared by a wider group of menswear guys seemingly diluting its “cool factor” until you take the wider scope of fashion into account, when you realize that its still not “cool” at all. Ugh. How exhausting!

For example, I remember once where a guy lambasted me in my DMs for seemingly pushing an agenda that grey suits aren’t cool, just because I mostly wear (and write about) brown and navy. I tried to counter with the fact that most menswear media (at least ones for beginners) tend to promote grey as the first suit to buy, which never fit in with my lifestyle or my preferences. I simply had to tell him that I thought brown and navy were cooler; no facts or data to back it up, just pure feeling. It only seems like brown and navy are the “cool” thing among the Big Menswear crowd because they aren’t corporate people, though I can tell you many redditors (and even my own friends IRL) still recoil at the sight of a brown suit. It’s all relative in the end!

Coolness isn’t even the only metric people have; some people dress functionally and others may not even have the word cool play into their style at all. Like with most things, getting caught up in arbitrary meanings is counter productive to the enjoyment of this thing as a hobby. Just focus on what you like and what you think is cool, even if others may not share it. Though I will say that it may help if you introspect and think about it, to see how it applies on a personal level. To make sure the coolness isn’t shallow but have personal depth and empowerment all rolled into one.

But for most people’s purposes, what’s cool is cool and what isn’t isn’t. It’s Best not to get caught up in it and not think about it too much. Perhaps the real question isn’t about coolness, but about effort and how it’s perceived. A subject for next time!