10 Simple Ways to Upgrade Your Style

You can be wearing the coolest, most expensive, well-fitting clothes, just screaming for a shot from Tommy Ton or Scott Schuman and on your way to Internet street style stardom, but if you don’t have an air of swag, confidence, or panache about you, then it can all fall terribly short. Looking like you’re trying too hard is one of the easiest ways to be deemed very unstylish and lame. Though very important, the biggest part of style isn’t the clothes one is wearing, but how closely the clothes fit the man’s demeanor. You don’t have to be insufferable or obnoxious, but quietly letting everyone know how confident you are in what you wear is louder than you know.

Between thrift shops, online forums, and your dad’s closet, you can easily find some dope used clothing that suits your style but won’t make your wallet cry out in pain. Style is cyclical, so you’d be hard-pressed to visit a thrift shop and not find some goodies that were “groovy” or “sharp” when your parents were courting each other, but are way back in style now. Learn the terminology and ways of buying from the best online clothing forums. That floral shirt you couldn’t afford last season but thought you’d die without? Well, it’s been gently worn twice, but is $50 less on that forum, bruh. No better score than a slightly used but way cheaper score. It hurts to say this, but Macklemore may have been onto something…

Got a hole in the elbow of your sweater? Learn how to sew a patch over it. Got a dirty spread or button-down collar on your oxford shirt? Cut the flap off and make it a band collar shirt. Customizations give old clothing items that are on the brink of extinction that breath of life to prosper as if they’re brand freaking new.

While it’s hard to predict what you’re going to like in the next two months—let alone five years—there are certain things you know you have to have in order to feel good in what you’re wearing. Leather jackets. Denim you have to beat up in order to give it some life. Even a grey crewneck sweatshirt. These are things that are style staples you can spend a few extra bucks on because they will never go out of style and they literally crossover every genre of style.

It is impossible not to follow the constant stream of trends, picking and choosing which one fits your current style. It’s also impossible not to want the very best, whether it’s from Alexander Wang, Balmain, or Margiela. But the Zara’s and H&M’s of the world are hip to these trends and are supplying them for less. It’s okay to pickup an item here or there, especially if you don’t see yourself wearing it forever and ever like people pretend to think they will.

Multi-season items that actually serve their purpose are pretty hard to find. Especially if you live in an area where the change in weather is so drastic. When shopping for new items, stop and think, “Will I be able to wear this in *neighboring/opposite weather season* or nah?” If the answer is no, then you may need to re-think things. M-65 Jackets are perfect in spring and fall, but can be worn as a layer in winter and as a cool night cover-up in the summer. Four seasons equals the possibility of 365-day wear. Impossible to talk yourself out of items like that when you truly break it down.

Face it, most clothing you buy off the rack won’t fit you right unless you are a perfect sample size. You could anticipate that you’ll grow into it, but a tailor can work wonders for you in any circumstance. Want it to fit now? Your tailor’s got you. Think you want to wear it down the line when you’ve grown a few inches or put on a couple extra pounds? The tailor will work their magic so it can be adjusted as you grow. Tailors aren’t clothing alterers; they’re magicians and they are at your whim.

While they may not always be the biggest or boldest items you’re wearing, accessories can be the most noticeable to the trained eye. A dope bucket hat can set your fit off like crazy, but a fedora out of context will make you look like you just got out of a Nickelback concert. Some crazy socks that peek from out of your turned out trousers? A dope backpack that carries your books, lunch, and catches everyone as you walk by? Those will likely land you your most prized accessory: that beautiful young lady you’ve been eyeing all year walking with you on your arm.

You want so bad to slim up your denim, but your athletic thighs won’t let you. So what now? Well, don’t force it and try to go with some super skinny jeans if they’re uncomfortable. Because if they feel uncomfortable, imagine how they look. Try on a few different styles to see what’s comfortable to you and get a few opinions. There’s nothing wrong with having some friends give you their two cents on if something looks cool or is wack. And if they can’t be truthful or won’t take it seriously when you’re trying to upgrade your style and give yourself more confidence, are they really your friends in the first place?

Part of being stylish is knowing what to wear in certain situations. You don’t wear a T-shirt to a wedding, but you don’t wear a suit to a basketball game. That’s not to say that you have to dress like all the other lames in your school, but being able to dress for the situation with a heightened sense of swag is what will set you apart. You don’t have to have the most outlandish outfit to stick out, you just have to know what to put together and when to put it together.