Last week I was at this coffee shop in Southeast Portland and this guy walks in wearing samurai armour. Like, actual armour. Plates for shoulders and arms and… okay, maybe it wasn’t full armour.

But, CLOSE ENOUGH. Head coverings and torso plates for sure. And he was wearing them with skinny jeans and Vans.

It wasn’t my first reaction to think “damn, that dude’s creative.” My first reaction was “shit, someone told this poor guy he looked like a cartoon and he believed them.” Look, man, I get it. Trying to look cool when every other guy is wearing graphic Target shirts for self-expression is tough.

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Believe me, I’ve made my fair share of questionable choices when it comes to clothing.

Like that time I wore Supreme box logo hoodie to every single social outing for like a year straight. Emma still brings that shit up anytime she’s trying to win an argument. My point is, there’s a difference between having an eccentric piece or two and becoming “that guy.” That guy with the fedora.

That guy with the suspenders. That guy who wears fingerless gloves all year round because he thinks it makes him look literary. (It doesn’t.) Once you become THAT GUY, you’ve stopped expressing yourself and started performing. My friend Jake made this mistake a few years back when he entered his leather jacket phase.

Every. Single. Day.

Jackets were his thing, and he wore one everywhere, rain or shine, hiking boots and leggings or jeans and dress shoes. Did he own shirts that didn’t clash with that jacket? OF COURSE HE FUCKING DID.

But he wore it so often that people wouldn’t invite him to pool parties because they knew he’d arrive in leather and refuse to take his jacket off, pissing in the pool instead of admitting the jacket didn’t work for that particular occasion. “He was my style icon growing up, so I always loved him dressing like that,” he told me recently when we caught up. “But then I realised that *everyone* was asking me about my jacket. Like, they didn’t see Jake wearing a jacket. THEY JUST Saw.

THE. JACK.…It hit me, man. I’d become a caricature of myself.” And that, folks, is what happens when you build your entire wardrobe around one feature.

You put yourself in a box. Literally and figuratively. You can never branch out, never experiment, never change because everything you own now serves a purpose to that main thing you wear.

You become The Shirtless Guy, or The Guy With Glasses On His Neck, or… well, you get the picture. Lately I’ve been worried that I’m falling into my own stylistic trap. I love vintage band tees and I have like sixty of them, which I wear ALL THE TIME.

Not because I want to say “look how many vintage band tees I own,” but because they’re comfortable and practically all of these bands are ones I listen to AND they go with everything. BUT, Emma made me realise that we had went to four concerts and a BBQ in a row and I’d worn a band tee to every event. Which doesn’t seem AS bad when you take concerts out of the equation, but now I look around and think “are people thinking I only own band tees?” AGH!

See what happens? One obscure article of clothing becomes your entire wardrobe until suddenly you’re Samurai Jacket Coffee Shop Guy and you can’t help but look around to see if anyone’s taking your picture. The thing about cultivating – IDEALLY – actual style, as opposed to a “look” or a gimmick, is that it shouldn’t feel like a choice.

Now, I know what you’re going to say: Of COURSE it’s a choice. You have to choose what to wear every day. What I mean is that it should come natural to you.

Not that you don’t think about it, but you know yourself so well that you know what works for you and what doesn’t. You know what clothes make you feel good and you just… wear those. My friend Aaron has this down to a science.

This dude could be wearing alligator boots with a paint stained tee shirt and I’d still have no idea what his “signature style” is because he always looks incredible and he always looks like Aaron. How? Dude layers well, keeps himself balanced, but also knows his classics.

He’ll throw a flannel over a jumper and denim jacket but balance it with a plain white tee. It’s simple, but it’s not as simple as picking one article of clothing and wearing that into every aspect of your life. My style is kind of all over the place, but I know mine falls into a few consistencies.

For me, I love mixing streetwear with classics and dress clothes. So I’ll throw on a Supreme hoodie with wool trousers and leather boots. Or vintage Jordans with a button-up and blazer.

Simple as that. Part of having flexibility in your wardrobe is making sure you have STYLE BENDERS. Stuff that you can wear for multiple occasions.

When I was really into hypebeast shit I realised I had fifteen goddamn hoodies I loved, but not one of them I could wear to a wedding or a bar or pretty much any place where adults were expected to wear clothing that didn’t resemble pyjamas. These days I make it a point that pretty much everything in my closet can be worn in at least two ways. Those crazy trainers?

Sure they look good with jeans, but they ALSO look good with tailored trousers when I need to dress it up. That vintage Carhartt? Great daily jacket but it also throws off just enough curveball to work as a layering piece over a button-up for dinner.

I read this interview with this older British style dude (Legend? Ran some trousers company?) and the journalist asked him what his signature look was and he looked at him like he was crazy. “Oh I don’t know. I wear things I like and things that fit.” And you know what?

Looking at photographs of him throughout the years, it WAS his signature. There was just something effortlessly him about it all. There’s no secret giveaway at the end of this article to help you discover your own signature style, but I will give you a few pointers on how to get there without dying as Samurai Coffee Shop Guy.

Figure out what you like to wear. Sounds simple, but be honest with yourself. What do you actually gravitate towards?

Make a note on your phone (I have a note on mine) of outfits you wear that you feel really pulled together in. Got compliments? Write that down.

Laughed with friends about how great it looked? WRITE IT DOWN. After months of this you’ll start to realise patterns.

Try things out at home first. Love weird military surplus jackets? Try buying one and wearing it around your flat for a week to see how it feels.

Something doesn’t feel “you?” Don’t sweat it. Lemme clarify that. DON’T BUY IT.

Live your actual life. Guy I know loves these beautiful Italian leather dress shoes he sees in magazines. Problem is, he walks two miles to work everyday and it rains in Portland like eight months of the year.

So those shoes never get worn and he’s wearing the same pair of beat up Adidas he’s had for years.

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Your style should fit your lifestyle. If you HAVE to alter your day-to-day life just to maintain your style, then your style doesn’t work for you.

Style itself is confidence. If you aren’t feeling what you’re wearing, you aren’t going to pull it off. It doesn’t matter if you spent $200 on that shirt or got it off the clearance rack at Urban Outfitters.

COVERAGE COUNTS FOR NOTHING WHEN YOU FEEL FINE. Samurai Jacket guy might love what he’s wearing. Maybe it makes him feel connected to his childhood, or happy, orcomfortable.

I don’t know him, and frankly I don’t care to learn. My guess is he rocks that jacket around his bedroom like he’s in season 8 of Game of Thrones, but the second he leaves he’s Steel Jacket Guy wearing … well, you know. That’s not style son, that’s performance art.

And if you’re not David Bowie, it’s probably best left to the professionals.

Author carl

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