The Hipsterization of Classic Menswear

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

Chime In

  • Jack of Clubs

    Now I have to know; what was the store?

    • Brian Sacawa

      Not going to say.

      • Jack of Clubs

        Very diplomatic, sir.

        • Brian Sacawa


  • Jose Grau

    Loved this article Brian. Thanks for sharing and sorry you had such an unfortunate experience.
    You guys at HSS are doing great ans inspiring work. Thanks again

    • Brian Sacawa

      Many thanks, Jose. Always appreciate the support. Cheers, my man.

  • Derek Shakespeare

    Totally agree with your sentiments on this Brian. I’m very unimpressed with any form of elitism or snobbery amongst those who appreciate fine menswear and good quality clothing etc. I’m all for inclusiveness and encouragement for those showing an interest in better dressing and such pursuits. Such a positive approach lends itself to a much increased awareness and appreciation of style and sartorial endeavours.
    Enjoying your blog immensely, by the way.

    • Brian Sacawa

      Appreciate you chiming in, Derek. And thank you so much for the kind words.

      • Derek Shakespeare

        Thank YOU Brian, for the informative and entertaining blog. I’m an avid reader of yours amongst several notable others. All for the better advancement of my knowledge and perhaps to aid my own sartorial endeavours. Keep it coming. Your readership are surely very much appreciating your fine work.

  • Will Field

    You’ve hit the nail on the head mate! Couldn’t have said it better myself. I’ve always had respect for great style but the time and respect exchanged with any person is not earnt or exclusive to this virtue alone. 🤜🏼

    • Brian Sacawa

      Thank you, Will. Quite well said yourself, if I do say so.

      • Will Field


  • Bandidos

    I must say that sometimes the “I’m treating you like a shit cause I’m much better than you” works, and works more as the distance increase. Coming down from Middle Ages times? I don’t now, but for some people it works, misteriourly.

    • Brian Sacawa

      Could you give an example of when you think that kind of treatment works?


    A shmata salesman with attitude? I would just love to deal with one of those. I could teach him a lesson in arrogance and condescension, being a lawyer and all. Bwoohahaha!

    • Brian Sacawa

      Wouldn’t want to be there for that! Or maybe I would…

  • asian_dapper

    I’m going to swing on the fence for this one and say this store is Suit Supply.

    • Brian Sacawa

      Going to interject just this one time for anyone else reading the comments – not going to confirm or deny any speculation! Though you all are free to speculate amongst yourselves.

    • Jim Sears

      Ha, my first thought too. I’ve had to put Suitsupply guys in their place once or twice. Though, on the whole, I’ve been happy with them and found them to be cool guys.

  • Mark Johnson

    I was that guy for a brief moment (much to my chagrin), but in a ski shop rather than a bike shop. Came back to Michigan after spending a season in Vail and thought I was cooler than the weekend warrior shoppers because I’d lived it man. Thankfully the owner saw it happening early on and rather than firing me on the spot he gave me a stern talking to. Problem solved.

    • Brian Sacawa

      Mark, it’s good that you were receptive to your boss. Some people never really get it – or their bosses just don’t take the time to correct them.

      • Mark Johnson

        Yeah he made me realize it just makes you come of as kind of a dick to most people…and who really wants to come off that way? I didn’t even really set out to cop an attitude intentionally but I’m glad someone corrected it.

        • Brian Sacawa

          People who are just too cool for school.

  • Mikkel Kjerumgaard

    Personally i like the hipsterization, mainly because i like pairing a bit of street style with classic menswear. As a young guy (17) i feel like now is time for me to go a bit of the box and try some oufits, which are odd and speciel, while still trying to keep the of classic menswear.

    • Brian Sacawa

      Thanks for the comment, Mikkel. I think we might be crossing wires on hipster v. trendy, say. I’m talking more about an attitude thing, rather than particular affectations. Though there are certain affectations that go along with the hipster attitude, which I name in the article.

      • Mikkel Kjerumgaard

        Well hipsters and dandys are becomming more out in the open, so it will should pop up and than “die down” again like any other trend.

  • OldManJoe

    Very good topic. I’m really sorry to hear how that experience went for you. When I started out with this “hobby” of mine, I got some snob comments about trying to be an “iGent”. You can guess that the term means someone who learned to be a so-called gentleman by reading stuff on the Internet rather than some other snobby, pretentious place.

    When I wanted to move up to bespoke, I was concerned I’d get major elitist attitude from a really upscale tailor. But, I made an appointment, had my first visit and found he was very cool and wanted to get to know me so he could make stuff that fit my personality and lifestyle as well as my body. He was very sincere and engaged. What a fantastic experience!

    Bike shop or haberdashery… if they are so well off they can treat someone badly, their shop deserves to die. :-)

    • Brian Sacawa

      Great comments, Old Man Joe! Thanks, as always. Great to hear about your bespoke experience. You’d imagine that someone in such an intimate field would be particularly welcoming.

      • OldManJoe

        Thanks, and I love, love, love the jacket (and the rest of the ensemble) you are wearing in the photo!!! Awesome!

        • Brian Sacawa

          Ah, many thanks. That’s the first suit I got from Michael Andrews Bespoke. Posting the second on Friday!

  • Jim Sears

    Did I just read the greatest Yelp review ever? I could write a book on hipsters. I used to get intimidated by the snobby clothier, but now I’m too old for that nonsense. Thanks for the input kiddo, now put that down and bring me a jacket size that actually fits.

    • Brian Sacawa

      Haha. Thanks for the comment, Jim.

  • GregsStyleGuide

    Haha I’m all too aware of the style forums you are referring to in your post. The ones just teeming with snobbery and an air of full-of-shitted-ness. Lol I agree that it does more damage than good to the culture of “traditional menswear” enthusiasts and alienates those who seek to learn more. Good thing that there are influential platforms like this to let people know that in this community, there are enthusiasts and influencers that are self-aware and down to earth. Great post.

    • Brian Sacawa

      Appreciate the support, my friend. Thanks for chiming in.

  • Luis Martinez

    Most of my friends who very well know my style, keep telling me they love my looks but they will never go to a tailor because it makes them feel dumb and/or ripped off in the end. So this attitude has become “the standard” for the industry unfortunately. I have experienced that myself many times and the final conclusion is that I will never go back to those tailors. It’s rather perplexing to me that they have not realized their customer service behavior is tightly related to their income. It sounds logical, right? and yet, they don’t change. There are many men out there noticing and wanting to improve their attires, but there are no incentives from the right sources, which by the way is another reason why fast-fashion is winning so many people.

    • Brian Sacawa

      Tailors can be interesting sometimes like that. I’ve been to a couple that are very closed minded when it comes to the question of how something should look or fit. That’s not going to produce a good result. You’ve either got to be extremely determined and sure of yourself or find another tailor. That’s one relationship that’s extremely important in the menswear world.

    • Khoi | Gentleman Within


      I believe we met at Lange the other night. Was a pleasure to meet you and chat for bit. I have to agree with your sentiment that many men out there want to improve their style. And I believe sources are out there, but are few and far between.


  • Mark Hugo

    Thank you for posting this Brian. I’ve been reading your columns and articles for some time and like all that you do. This, though, is the first article to really struck a chord with me, especially since I don’t think this is a recent trend — as you note, its been going on for a long time in many other spaces. In my case, its been a decade of attitude and bad fit at clothing retailers, bespoke suit makers, tailors and more. I’m short and I’m overweight. I want to look nicely put together in a suit (for work and for fun), just like many other men do. I can’t tell you how hard it is to find a store or vendor who doesn’t have some attitude about heavy people. (I wasted thousands on bad fitting clothes that came with lectures about how hard it is to fit people like me.) Couple that with the hipsterization going on, and, well, I’ve literally stopped shopping at my local stores. Plus, my favorite salesman retired and my favorite tailor moved to Florida.

    My apologies for going on, but wanted to chime in. Thank you again for this post. And keep up your good work! Its appreciated.

    • Brian Sacawa

      No need to apologize, Mark. We’re here for discussions like this. I think men with a belly have great options for style, especially when it comes to trousers and braces. It’s too bad that the tailors you visited foisted their opinions on you. A good one would size you up and get you into something that would work for you. Have you found anyone after your guy moved?

      • Mark Hugo

        Thank you for the note Brian. And no, I have not found a good alternative. I am looking though and plan to try someone in DC who comes recommended.

  • David Starzyk

    What saddens me the most is that personnel like that, along with some of our fellows, might squash an interest in something that is, truly, a joyful part of being alive. There is nothing better than being fully turned-out; if others actions are cause for squelching the potential to experience that joy, that is just a damned shame.

  • The Hyson

    Great article Brian. I think this elitist attitude may be prevalent in many different pursuits. From style to sports, wine, food, etc. It can definitely be intimidating if you are on the learning curve. I would think that with less style rules (a little more of anything goes for men’s style currently) it would create more free expression and less snobbery. Like minded people with similar interests should support and encourage each other. I enjoy seeing a man put forth an effort in his style even if it doesn’t hit the mark and I think this should be encouraged. For every great outfit we all have our share of misses. Keep up the good work. Cheers,

  • Anastacio Casillero

    I have to agree with you that there are many places that the second you get in, they begin to size you up and judge you. I just think at the end of the day for the most part we don’t need to dress up anymore as people used. Those of us who like to dress nice, we do it because want to. I work for a big bank and even business attire means to wear pants, dress shirt, and jacket. Anything above that, fit, style, and quality is just not really necessary which is good and bad. Like everything in life.
    I also want to point out that even your site feels to me a little way too high end and out of reach to me now. I like your style but long are the days where I would see something you would be wearing I could go and buy it. The Timex has been replaced with $20,000 plus watches, Jcrew jackets are now replaced with $900 jackets.
    What I am saying is don’t forget about the regular working person who likes to dress nice but can’t spend $6000 on a suit. And yes I get it, that everything you wear can be purchased of similar price, but it was more fun when you would wear $250 jacket, with nice shoes and a simple watch and I could out and buy something similar and know that it was nice and attainable.

    Thanks for all the ideas.

    • Sifat Sartaj Turja

      I believe style is a very personal thing. Where Brian is wearing an expensive Rolex diver watch, you can get the same style from Seiko at an affordable price range. Even if that’s too expensive for you, you can go for a Timex diver (around 70-100$), and still look great and have a good watch. Everything in life is supposed to improve, and so did Brian’s style, blog, and obviously his income. We definitely should not be discouraged by it, rather we should be more motivated from his experiences.

  • Michael Geary

    Brian – Another good piece. I’ve intentionally “dressed down” before for fear of ridicule or judgement.