Get Shorty: How To Wear Shorts The Right Way

Shorts have come a long way since their humble beginnings, following World War II. Since then, they have evolved from being just a utilitarian way to beat the heat, to securing a place among the ranks of some of the most fashionably elite. Although shorts probably won’t ever become the boardroom standard (outside of Bermuda anyway), and we're definitely not endorsing man-capris, there are still ways to pull off the most casual piece of clothing next to the t-shirt, while still looking sharp and stylish.

Lock In The Right Length
There’s no hard-and-fast rule as to how long a proper pair of shorts should hang, part of it is preference, part of it relates to how tall you are, but we do suggest going no higher than a 2-3 inches above the middle of your kneecap, for the most reasonable look. While it seems some brands are favoring a Daisy Duke vibe these days, somewhere between an 8 and 12 inch inseam is probably your best bet. Conversely, shorts that drape too far below the knee can make you look like a child trying to wearing your older sibling’s clothes and also shorten you overall. Let’s face it, nobody wants either of those things.

Casual vs. Comfortable
After a long day at work, school or wherever your couch isn’t, there’s nothing better than letting loose and throwing on a pair of those cut-off sweats or mesh basketball shorts. Yes, shorts are inherently casual, but because they now are cut trim and come in rather stylish fabrics, like chino, linen and chambray, not all shorts are created equal. For a relaxed day out, ditch those frayed jorts in place of a smartly cut, modern-fit pair of chino or twill shorts. It’ll allow you to maintain all the comforts that come with wearing shorts, without looking like you just woke up. You’ll be able to dress them up appropriately with a collared button down or polo and even wear something dressier than a pair of sneakers with them. And let’s leave the meshies at home, relegated to watching sports or a Netflix binge session. You never know who you are going to run into on your morning coffee run, so it’s worth it to consider what you leave home in.

Mind The Dress Code
More and more, offices are allowing employees to take full advantage of a “casual work environment”, which includes wearing shorts to work. While we don’t unanimously condone that here, there’s nothing wrong with wearing a smart pair of shorts if the dress code explicitly allows it. But, that doesn't give you free reign to wear cutoff sweats or cycling spandex, there are limits to what types of shorts you should wear in a professional setting. Treat your shorts as you would a pair of more formal pants (like chinos) and keep them dialed in with the right shirt and shoes. As for summer events, weird dress codes can be confusing, but we don’t recommend shorts unless it explicitly states "casual" and it's a daytime or outdoor setting. Don’t be “that guy” who shows up in shorts and a ridiculous hawaiian shirt, just because the wedding invitation said “beach side”.

Don't Forget The Shoes
Contrary to popular belief, when wearing shorts, there are other footwear options besides flip flops or canvas sneakers. If you want to sharpen up a touch for a relaxed evening out or if you’re headed to a BBQ, try a pair of suede driving loafers or boat shoes along with a long sleeve plaid or oxford with the sleeves rolled. With a look like this you’re going to be able to hit the perfect stride between casual, comfortable, and dressed up.

Finding the right pair of shorts, much like with any other article of clothing, is about nailing the fit and style that suit you best. There’s no magic formula to determine the perfect fit, but with a little due diligence, you’ll be able to pull off the summer casual look with a healthy dose of style.