The Number One Men’s Style Mistake (And How To Avoid It)

The bad news is that it is probably unavoidable

There are countless round-ups of the worst men’s style mistakes out there. I’ve done one myself. Most of those lists–mine included–tend to focus on things that are pretty cut and dry. Suit jacket shoulders too wide. Pants too long. Wearing a button-up shirt untucked with a blazer. Easy fixes, if not very mildly subjective.

worst mens style mistake

However, there’s an elephant in the room. It’s a mistake that I would say 99.9% of people make at some point. But it can’t really be packaged and tied up neatly with a bow, like the rules for wearing a tie bar. It is a mistake made with the best of intentions that always results in the worst possible outcome. And that mistake is, my friends, trying too hard.

worst mens style mistake

| WEARING | Drake’s shirt, Michael Andrews Bespoke pants, Oliver Peoples sunglasses, Rolex watch, Morjas loafers | PHOTOGRAPHY | by Rob McIver Photo

The bad news about this mistake, is that, unfortunately, I really believe it’s unavoidable. When you are new to the idea of classic menswear, new to the idea of using classic menswear as a vehicle for something else, it is empowering and is certainly instills confidence. However, that newfound confidence can often be misguided.

The first thing you want to do is specifically the thing that should be avoided. You want to show everyone that you are “into” style. You want to show people that you are “into” menswear. And perhaps, in some cases, that you “get it” and others don’t.

worst mens style mistake

This line of reasoning always leads to doing too damn much. You know the guys. Maybe you’ve been one of those guys. And, no shame, I certainly have. Three-piece suit with the tie bar, lapel flower, dub monks, boater hat, sunglasses, three or four bracelets, colored laces. You get the idea. But like I said, having been there myself, I get it, it’s a natural overcorrection, and honestly, not so easily remedied.

The confidence and swagger that “finding” menswear can instill can be a double-edged sword. On the one hand, it emboldens one to say, “fuck you,” to all your friends who are 15 years out of college but still dress like they’re 18 years old even though they’re approaching 40. And that’s a good thing. One has to grow up and how we dress is an important facet of growing up. But on the other hand, that confidence can lead to some pretty poor choices, including, but not limited to, the faux dandy described above.

worst mens style mistake

So what is a guy to do? Be confident, yes, but realize that going overboard does not equal better style. In fact, less is often more. And honestly, it takes just as much confidence to do less. And that is the point when the quote unquote minor details come into play. I’m taking about the fit and length of your trousers. Do they have side adjusters? A cuff? How you turn up your shirt cuff. Have you replaced your steel watch bracelet with a leather strap because you know you can and know that it will draw in the color of your suede loafers?

All of these are things that, to be perfectly honest, probably not many people are going to notice. To the vast majority of people, you’re going to look really put together. They won’t know specifically why, but they will know. A small percentage of people will totally get it though. These are the folks you want to have a deep conversation with over a great Negroni and fine cigar.

worst mens style mistake

The irony of all of this is that the appearance of ease and nonchalance is often carefully studied. A truly stylish man will look as if he wakes up that way. And now I’m going to be exceptionally real with you–nobody wakes up that way. It takes practice, it takes stepping in it and learning from your mistakes. Style is a journey. Style is a process. We are all students.

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style


Chime In

  • RJ Giddings

    It’s interesting w/ this piece, where Brian can illustrate what a lot of gentlemen should know, but maybe a lot of us don’t. Being dapper but a tad just too overboard with style. There’s something ingrained in us – from the time we are kids- where we really want to show you our new shoes/ threads. I can think of ‘back to school’ shopping with mom. First day back at school – all the kids are showing their new wares. And then fast forward twenty or thirty years- and the same mindset can happen with dapper guys who like to peacock a bit. 10% too flashy, maybe 15% trying too hard. You’ve got fashion magazines and fast-fashion industries that are keeping this propped up. I’ve been guilty of this. It happens. What I like about HSS is – the difference found here – and the lessons taught are : to slow it down, find your own style, stay classy and don’t look like your trying too hard. Keep it real.

    • Brian Sacawa

      The back-to-school notion is really interesting and one I hadn’t thought of. It’s totally true! I always wanted “the” pair of sneakers for the first day back to class after summer vacation. On the menswear tip, I have personally toned it way down over the past few years and it is completely by design. I’m more interested in cultivating a timeless style that I’ll be proud to look back upon many years–decades even–later and still be able to say, yeah, that was just right.

  • Tony_Ieradi

    Good advice. I am always cognizant of what I am pairing with what. Maybe a great pair of shoes and not the great shirt as well! And the one thing that kind of drives me a little up the wall; the clashing belt and shoes. It’s not hard to coordinate the same color.

    • Brian Sacawa

      Oh, you definitely need the great shoes and shirt together! Just maybe skip also adding three bracelets with skulls, a lapel flower, a boater hat and socks that match your pocket square.

  • Khoi | Gentleman Within

    Great piece on the style journey. We’re all on this journey, though not all are cognizant of it. But surely there are levels and one cannot simply go from zero to 100 overnight. It takes time and I’d have to agree that a major mistake every stylish guy has made along the style journey is the overcorrection phase of appearing to be into style. Overtime one learns that less is more. I like the line, “the appearance of ease and nonchalance is often carefully studied.” Having sprezz comes from years of practice.

    • Brian Sacawa

      Definitely a learning experience and one everyone will make mistakes at along the way. My mistakes live deep in the HSS archives!

  • Dorian

    Nice watch for me, though there is a lot not going well for this guy.

  • Cosmos Studio

    Second that, Brian. Trying too hard not only reflects poorly on one’s style, but also incentivises them to purchase clothing they won’t wear – the clothing that will end up in landfills prematurely. Buying clothes we absolutely love is one of the pillars of sustainable fashion shopping.

    Thanks for this post!

    • Brian Sacawa

      Thanks, guys. Yes, sadly, impulse buying is still a problem in menswear. I would take what you say even further and say that people often sacrifice quality for a quick fix just to be able to have that suit/blazer now.

  • Kyle Miller

    I love those loafers! I normally where a 10D but am unsure if choosing a 9.5 UK size is appropriate on the Morjas website. How do these fit for you and what would you recommend for best sizing?
    Thank you for your time.