The Guide: Shorts for Every Occasion

July 7, 2017

Summer crept up on us this year. We’ve got another two months of hot & humid days ahead, which means you need to be ready to rock shorts for every possible occasion. Do yourself (and your boys) a favor — stock up on some breathable options for downstairs.

Just like with your pants, you should plan your shorts rotation with versatility in mind. What works at a pool party won’t at the office… you know the drill. Let’s take a look at every occasion you’ll face this summer and break down what you’ll need for each.

The Office

Before we dive in let’s be super clear: if it hasn’t been overtly stated that shorts are cool at your office, err on the safe side and don’t risk it. For those who are fortunate enough to work in offices where shorts are cleared, you still want to err on the safer side when it comes to the shorts you do wear. Go with classic cuts (AKA it has a button and zipper). Basically, think chinos, but shorter. Ted Baker has you covered.

Ted Baker – Exsho Geo Print Chino Shorts ($175)



When you’re looking for off-duty shorts, comfort is key. So is something that’s easy to pair with any shirt on the top. We love this pair from Barney Cools. They’re comfy as hell and the neutral beige colour goes with anything — from tanks to tees to patterned button downs. These will be your instant favourite.

Barney Cools – Chino Drawstring Short ($100)


Nighttime BBQ

Your buddy is hosting a BBQ that will no doubt turn into an all night rager… and it’s 34 degrees & climbing. You’re going to need shorts that are basically the more breathable equivalent of distressed denim — stylish, comfy, and definitely nowhere close to anything found on Middle Class Fancy. Just like on the denim front, the guys at Kollar have got you covered.

Kollar – Coated Denim Moto Short ($149)



Poolside is where you can have the most fun and earn some real style points with your shorts. When it comes to bathing suits, we’re all about the prints. Because you’ll be rocking them sans-shirt (or with just a basic top)… go wild! If you’re comfortable in them, you can pull them off. Just make sure they hit somewhere above your knee and a good couple inches below your junk. Within that range, it’s up to you how much thigh to show.

Handsome Me – Flamingo Trunks ($75)


Bonus: Pro Tip

When you’re wearing shorts, all of a sudden your boxer game becomes a whole lot more important. The risk for accidental undergarment appearances skyrockets. And it goes without saying that your boxers need to be skintight (for your sake and others’). Grab a pair of SAXX. You can’t put a price on ease of mind, let alone comfort.

SAXX Vibe Boxer In Pineapple Bomb ($33.95)



• Shop a bigger selection of men’s shorts here.