Men With Terrible Style: Don’t Let Your Clothes Wear You

a man with terrible style

A man with terrible style | iStock.com

With somewhere around 100 colleges and universities located in the greater Boston area, living here means almost constantly being around college students. It also means I get to see guys in all stages of figuring out how to dress themselves. There’s obviously no age where guys are required to learn how to dress, but college is one of the first times we’re forced to make most of our own decisions, and that includes clothing decisions.

Boston is also not known for being a particularly well-dressed city. The number of cargo shorts still being worn is far too high, and it’s not uncommon to see basketball jerseys and athletic shorts being worn in restaurants where dinner and drinks for two will easily run you $100. Not everybody dresses like a slob, but it’s still pretty standard.

In an effort to stand out from their cargo-short-wearing classmates, you also see quite a few guys trying to up their style and dress a little better. Unfortunately, most of them fail to pull off their new clothes, and it’s not because of the clothes themselves: It’s because they make the classic mistake of letting their clothes wear them.

dress shirts

Dress shirts | iStock.com

It’s not the whole problem, but the way their clothes fit is definitely part of it. If a guy who should be wearing a medium gets a great deal on a very nice Brooks Brothers shirt, but it’s an extra large, no one is going to notice that he’s wearing a nice shirt. All they’re going to notice is that it looks like he borrowed a dress shirt from his dad.

I recently walked past a guy wearing a pair of brightly-colored, patterned shorts. If they’d been a size larger, he probably would have been able to pull them off, but unfortunately, they were awkwardly short and squeezed his thighs a little too tightly to look comfortable. Instead of thinking, “Hey, those are some pretty cool shorts,” my immediate reaction was, “How did he squeeze into those, and why would he want to?”

It’s also not just about the individual items of clothing you wear. The best-dressed guys coordinate what they’re wearing to make sure it all works together. They choose their shoes, socks, pants, belt, shirt, and jacket to all go together. They don’t, for example, go to a meeting wearing a conservative suit and pair of brightly-patterned socks. It’s out of place and doesn’t fit the occasion.

a man with terrible style

A man with terrible style | iStock.com

If that same guy wore those brightly-colored socks to a wedding with a tie and pocket square to match, that choice would work a lot better.

That’s part of the reason a lot of hats receive so much hate. James Spader can pull off wearing one as the character Raymond Reddington on The Blacklist because it fits with his character and the rest of his clothes. Reddington’s character would actually look incomplete without that hat. If an average guy tries to wear a fedora, it’s just going to look tacked on.

Whether you’re wearing unique socks, patterned shorts, an expensive shirt, or a hat, you don’t want it to look out of place. Instead, it will always look better to wear clothes that naturally go together and fit the kind of guy you are. There’s nothing wrong with taking risks or trying out a new trend, but making it look natural means learning how to wear it right. There’s also usually more going on with a trend than buying one item of clothing or making a single style change.

Dark blue small checkered formal mens suit

Dark blue small checkered formal mens suit | iStock.com/fotobyjuliet

How do guys who wear trendy shorts wear their shirts? What kind of shoes do they wear? What kind of socks do they wear? When they roll their sleeves or cuff their pants, how are they doing it?

You don’t want to be asking yourself, “Can I pull off wearing this?” If that’s the question, you probably can’t. Instead, try to figure out how to integrate what you wear into a single look. If you pay attention to the details and focus more on the whole outfit rather than just one item of clothing, you’ll be better able to coordinate your look to make sure you’re the one wearing your clothes instead of letting your clothes wear you.