Skip to Main Content

The Hipsterization of Classic Menswear

May 8th, 2017

A new direction or a bump in the road?

One of the main reasons I started He Spoke Style was to make men’s style more approachable to the regular guy. There is certainly no shortage of information out there on how to dress, how to build a smart wardrobe and so on, but a lot of that information tends to come via any number of men’s style forums. And while there is definitely some good information in those forums, the range of opinions can leave one more confused about a subject that before happening upon a certain thread.

But more to the point of a driving factor behind HSS, was the amount of pretension and elitism espoused in said forums. The I’m-smarter-than-you attitude and you’re-an-idiot-for-not-knowing-this-stuff-in-the-first-place sentiment creates a climate that does no favors for anyone and most certainly puts off many well-intentioned guys just looking for advice on how to dress better. Some people, man, I tell you…

I bring this up because although I think we’ve been doing good – I have no empirical evidence or scientific studies to cite, rather I go off my perceived level adoption of and caring about better dressing habits among the wider public, specifically some of my “regular guy” friends, who turn to me more and more for advice rather than making off-handed snide comments about what I do – I’ve sensed a small trend towards elitism in certain segments of the menswear community.

I’ll give you an example, though I’m not naming any names.

Not too long ago, I made a pilgrimage to a well-known menswear shop. I say pilgrimage because it’s not around any of my usual haunts or well-worn paths and is sort of a pain to get to. But, being such a menswear enthusiast and, I’d say, connoisseur of interesting, high-quality and, I suppose, “hip” menswear brands, I considered it my duty to see what all the noise was about, particularly given the rising prominence of this particular company.

Upon entering and taking a quick look around, I became aware that I was being sized up by the staff. The younger gentleman who came over to tend to me was particularly condescending and self-assured. I, for my part, was pretty vibed out and very turned off by the entire experience. Why act that way? I just don’t get it. Like, if your goal is to sell me a $1,500 jacket, a $450 pair of shoes or maybe a couple $200 ties, perhaps drop the attitude. If my money’s not cool enough for you, well, fine, I’ll just take it elsewhere.

The whole experience really brought me back to my bicycle racing days, when frequenting bike shops was de rigueur. Any novice, weekend warrior, kind of rider knows how snobbish bike shop employees can be, particularly the wrenches. If you don’t look the part, you’re not getting the time of day. I used to see it happen all the time. That’s why there’s usually one or two “regular guy” (i.e. non-racer-type employees) in any shop – to deal with the peasants (or “freds”, as they’re known) and make them feel comfortable.

Back to the menswear shop experience.

Now, could it have been this one particular employee with the pretentious attitude? Of course. And in the case of this particular establishment, I certainly hope so. But imagine the potential impact on someone new to the game.

I love to think about some of my just-coming-around-to-putting-some-thought-and-effort-into-dressing-well friends reading HSS, doing some other research online and on Instagram and deciding that this is the place they want to have a suit made. So they go there, get the same treatment and come back to me and say, “Man, fuck that! I’ve got better things to do than deal with people like that. I’ll never be a part of this club and, honestly, I don’t think I want to be.”

Segments of hipster culture have always appropriated elements of classic men’s style into their vibe, though they’ve tended to be on the grooming end of the spectrum. I’m thinking particularly of handlebar mustaches, undercut haircuts and beards. There has also been a strong and thriving dandy culture. But the one thing that strikes me about the particular grooming or lifestyle choices just mentioned, is that they were/are a way to identify with a particular group, to feel like a part of a group, to be included, not excluded.

However, my sense about some of the rising hipster trends in menswear – high-waisted pleated trousers, ties deliberately tied so the narrow blade hangs much lower than the wider one, et al. – and the tenacity and veracity they are being pushed into the consciousness as “this is menswear now, buy into it or get lost” is that they’re meant to be exclusionary.

This whole phenomenon could just be a routine ripple in the evolution and continuum of contemporary men’s style. It could also just represent a subset of gentleman that currently having a moment in the big edit of men’s fashion. And it’s possible I’m making a much bigger deal out of one shitty experience than I should.

The main point is that nobody wins when the attitude is elitist and exclusionary. If you love something – in this case, menswear – create an environment to inspire others to understand and embrace what you love too. That’s what we’re about here at HSS. But, man, some people, I tell you…

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style

Photography by Rob McIver Photo

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

All Posts