10 Signs You’re Trying Too Hard to Be Stylish

Casual bowties. Highwater pants. Camo down to your boxers' codpiece. For every trend and style, there are at least 100 ways to go overboard. Judging from the current state of menswear, plenty of people do. While men's style grows out of this awkward phase between high-end tailored gear and streed-cred worthy clothing, it's not hard to strike a balance between the two without looking like you don't know what's up.

Before you leave the house, check the mirror, and before you check the mirror, check out these 10 Signs You're Trying Too Hard to Be Stylish.

We’re all for pops of color, but too much is just too much. Once you cross over into looking like a Batman villain, your outfit goes from intentionally clashing to “I have no idea what the fuck I’m doing.” Show some restraint and go for one or two bright colors, whether it’s your socks or an overcoat. As long as it’s weighed down by some navy, gray, or black, you won’t look like a fool.

By now, you should know that co-signing certain brands will make you look like an utter douche nozzle. Ed Hardy aside, flaunting your Louis Vuitton Damier belt or Burberry plaid shirt is the more expensive form of stylish dickery.

If you've got cash to blow, opt for copping items with so-called “stealth wealth” in mind: luxurious items that are subtle in their design. Thom Browne's shirt tag and the four tell-tale stitches on the back of Margiela knits should be worn like a best-kept secret. Only the cool guys who pay attention to that sort of shit will notice and appreciate it, and going out of your way to point it out will make you look like an asshole with a credit card.

Look, what Kanye West and Kid Cudi wear is usually on point, but don’t make it your mission to wear the same exact shit they do. They’ve found what works for them, and that’s why they can pull it off. You’re not Yeezy or Cudi, but you might be inspired by them to rock a leather jacket in a certain way, or get turned onto a new designer or brand, and that’s fine.

Where it gets bad is if you look in the mirror rocking that Kid Cudi x Surface to Air Jacket, and despite you knowing deep down that it just isn’t your steez, you fork over a G anyway. Looking good means looking like you, but cooler. Don’t try to be someone you’re not.

In the same vein, while many men’s style blogs are a great resource for new brands, finding out how they fit in relation to what else is out there, and getting a headstart on trends months before the plebes find out, take all that advice with a grain of salt.

The last thing you want to do is look like you were “dressed by the Internet,” because often this means you’re so afraid to take a style risk because you don’t think the menswear blog illuminati will agree with your personal style. Fuck ‘em. Do you.

Image: Justin Chung

The saying goes that you should put on everything you want to wear, and then take one thing off. Nice bowtie, cool bracelet, sweet suspenders, oh you got a Jesus piece too? Seriously though, go for like a watch, a bracelet, and a tie, and that’s it. Or skip the tie and wear a chain, if you wanna be hood about it.

Rolled-up jeans? Check. Top button buttoned? Yep. Shirt half-tucked? Definitely.

Gross. How about you stop worrying so much about looking too dressed up and just wear what feels right? Mess around with proportion and context a bit, sure, but don’t get carried away with trying so hard to dress down.

Are you outside? Is it windy? Is your collar on a wool coat? Ok, you’re fine.

Are you indoors? Are you wearing a polo shirt? Is your name DJ Paul or Juicy J? No? Put that shit down, bro.

Pocket square never to your liking? Jean cuffs coming undone about half an inch? Leave them shits alone and let ‘em rock, b. If you keep fiddling with shit it probably means…

If you’re constantly wondering “am I pulling this off?” You’re not. If you check yourself out in every other window or mirror you pass by because you’re not sure if that jacket or pair of pants looks ok, that’s a sign it’s just not your style.

Clothing should enhance your confidence, not make you even more insecure.

Really dude? …But like, really dude? Sure, it’s cool to get flicked up by Mr. Schuman but if you get dressed every morning with “wait… what if I run into a street style photographer?” in the back of your head you really need to think about your life. Were you not hugged enough as a child? Did you have overbearing Asian parents that never gave you the validation you needed? Are you just that vain?

Style should enrich your life, not be your reason for living. Clothes are dope, and putting them together well does require a certain skill set, but anyone that defines themselves by their wardrobe, really needs to chill the fuck out. Real swag comes from a balance of knowing who you are and not taking yourself too seriously. Trust.