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Required Reading

The Style Mistake That’s Impossible To Avoid

September 11th, 2020

Don’t worry, it happens

Learning about menswear, developing a personal style, finding what’s right for you–it’s a journey. We are all on that journey and one of the things that is guaranteed to happen at some point along the way is that you will make some kind of mistake. You’ll probably make more than one.

Now, some of mistakes will be very easy to correct–there are tons of posts and videos out there about things you shouldn’t do, or style mistakes that men make. But there is one mistake that everybody makes, never included on any of these lists, that I feel is difficult to identify, difficult to address or remedy, but 100 percent guaranteed to happen to EVERYONE at some point during their style journey.So this particular style mistake, I would say typically, is something that we go through more towards the beginning of our style journeys. You know, just getting into it, not a whole lot of knowledge, but very curious and very eager to quickly get yourself to a very different place.

So as we’re doing this, as we’re adding pieces to our wardrobe, to dress better, to feel better, and kind of looking to be accepted in some way into this community of men who do dress well, we are bound to do the most terrible thing, I would call it the number one style mistake of all time, and that is we try too hard.

We’ve all been this person in some way at some time. If we’ve gotten past that, it’s easy to see and kind of recognize the signs. Generally, this person will appear a little uncomfortable and self-conscious, probably wearing a suit, quite possibly a three-piece suit, they’ve got the lapel flower, the tie bar, three or four beaded bracelets one of them with a skull on it, a fedora, basically going way overboard and probably wearing that stuff in a situation that would not require that level of getting dressed up.

Now why do people do this? I’ve thought a lot about the reasons behind this and why this is a thing that people seem to go through. And I think it boils down to one very specific thing. And that is that when you decide that you are going to start thinking about personal style, about how you dress, and you make that commitment to developing your wardrobe, that you’re super excited about this and you want people to know and you want to show people that you are into style.

This always results in going too far, doing too much, and trying way too hard.

Now as I mentioned at the beginning of this video, I think this is something that is completely unavoidable. Now, I sit here and talk to you about about style on the channel all the time, the He Spoke Style website’s been around for almost seven years, but that doesn’t mean that I haven’t gone through this either.

In many ways, the beginning of He Spoke Style was the beginning of my journey to where I’m at now. I did do a video about some of my worst outfits and some of those I classified as bad because I did feel as though I was trying too hard. I do want to show you here though just one of the things I’m talking about from my past so you can see that I too have been there.

Now, as I was scrolling through the archives of the Style guide on the He Spoke Style website, I noticed that a lot of the outfits that I would place in this try-too-hard category, were from the early days, maybe the first couple of years of He Spoke Style. So that kind of supports my theory that this kind of happens very early on in someone’s journey.

And the one thing that jumped out at me as sort of a turning point in my own style as I was scrolling through is that there was definitely this point where you can clearly see that I became more comfortable with the concept of less is more. The point where you discover that you don’t have to try so hard is really the turning point for every guy that gets into style and actually gets to a level where they’ve actually kind of figured it out.

Now, although I say that this mistake is unavoidable–it’s almost like a terrible rite of passage, in some ways–there are a few things I think you can keep in mind to help kind of check yourself as you go through this whole process. I’m not saying that if you do this that you will miraculously skip through this phase–though I hope that’s the case–but what it can do is just make you aware of it so you might be able to catch yourself a little bit before going too far.

1. Less Is More

The first thing to think about and remember is that less is more and subtlety, in my opinion, is the most stylish choice you can make any time  for any occasion. Doesn’t mean you need to be a super minimalist, but doing too much, you know the lapel flower, lapel pin, bracelets, like all that stuff together that I talked about already, is a dead giveaway of someone who is new to the game and trying too hard. There’s a great quote by Coco Chanel who said, “Before you leave the house, look in the mirror and take one thing off.” Though in the situation we’re talking about, it might be better to take more than one thing off.

2. Keep It Simple

Now with that, there is a certain amount of confidence you need to be okay with keeping it simple. Peacocking is one thing, that’s not what we’re talking about here. Someone who’s a peacock, typically knows exactly what they’re doing and why they’re doing it. It makes sense for them.

But if you’re green, so to speak, and you do all that stuff together, I guarantee that inside somewhere you will be questioning whether this is right. And that kind of self-doubt will definitely show and project out into the world. However, if you keep it simple, if you keep it classic, you can be super confident in knowing that you look put together.

3. Avoid Trending Accessories

Next, avoid trending accessories. I’m talking about things like lapel flowers, wooden bow ties, the hex tie, which I still honestly think was just some dude trolling the entire online style community, novelty cufflinks, novelty socks, unless of course it’s Christmas, then it’s okay to wear Christmas tree socks. All of these things are basically designed to capture attention very quickly and, in some cases, cheaply, meaning like through a gimmick. Gimmicks aren’t stylish, period.

The reason this happens is, what do you do when you make that commitment to developing your personal style? Yeah, you look online, you look on Instagram, but you also pick up the latest copies of Esquire and GQ. These magazines are always telling you what is trending. And sometimes, their advice is not so good, especially when it comes to these sorts of accessories. Again, keeping it classic, never a bad idea.

4. Stick To Basic Colors

Along those lines, another thing that happens is that we think about the basic menswear color palette–you know, your blues, your greys, your browns–and people very quickly get bored with that or think, oh, I’m going to be unique, I’m going to add a pop of color. I’m so sick of that phrase. Now, color is fine. But what happens in the scenario that I described is that those pops of color start to overwhelm every outfit. So it’s okay to be okay with the basic menswear color palate.

I’m not saying you have to be boring and completely swear off color, but if you find yourself thinking about your wardrobe in terms of, oh, you know, I have a lot of blues and greys and browns, but you know what I don’t have a lot of? Purple? Yeah, I should definitely get some purple, because I don’t have it.

That is not the way to approach your wardrobe. You don’t need all the colors of the rainbow to have equal representation. You don’t need to have every single color. Stick with the basics. Add in some color here and there–pocket squares and ties are good places to start. And just be confident in that.

So the bad news? You’re going to make this mistake. I guarantee it. The good news is that if you’ve watched this far, you are now equipped with a few things to be aware of to help you through what I really think is something that is completely unavoidable. The thing to remember is that you are not alone. Lots of people before you have made this mistake, myself included. Many times. And people will continue to do so. It’s fine. We all go through it. And now, unfortunately, there are lots of photos that we can look back at and laugh at, but also, learn from.

Thanks for reading.

Stylishly Yours,

Brian Sacawa

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.

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