Whenever I try to give advice on shorts - a notoriously tricky subject - there’s always one smug guy that says something along the lines of “I would NeVeR wEaR Sh0rTs.”
To this guy, I say, “look pal, I don’t love ‘em either. But it’s about to be hot out and maybe it’s worth giving a listen to what I have to say.”
Unlike summers past, there’s no agreed-upon inseam and styles are as varied as the sub-cultures that wear them. Pleats, jorts, flat front - and inseams anywhere from 2 to 9 inches seem equally in play. But we may have to go back in time to understand our collective shorts-avoidance.
A little History Because I love to Bore You
The reasons to dislike shorts are manifold. Maybe it’s because our style icons never really wore them. Maybe it’s because they can make you feel so exposed. But there are a few reasons buried in our collective unconscious that may be to blame.
“In short pants” - a (now) seldom-used idiom to connote naiveté and lack of experience. This phrase is a bit dated, but its roots are very real. For most of the 20th century, shorts were mainly reserved for children, because they grow… a lot. And clothing used to be much more expensive. Boys wore long socks and short pants until they reached adolescence, at which point, they would receive long trousers. (So there’s a historical reason you’re feeling infantilized.)
Men weren’t allowed to wear shorts! There was a great deal of consternation about men wearing shorts outside of army service, even as late as the 1960s. Sumptuary laws (dress code enforcement laws) beginning as early as the 30s strove to prevent men and women from wearing shorts in various towns and college campuses around the nation.
LA Community College students reading about a ban on shorts.
Our great-grandfathers aspired to leave shorts behind in favor of mature “adult” long pants and our grandfathers were punished when they regressed to wearing these childish and revealing garments. So, I think it’s fair to say our biases are understandable, but they can be unlearned.
Wear Shorts On Purpose
The worst pieces of clothing are the ones that can’t make up their mind. It’s why hybrid dress shoes suck so bad - a guy who’s only ever worn sneakers felt insecure about making a strong choice and wearing a regular dress shoe. The resulting ambivalence of design doesn’t blend in - it sticks out like a sore thumb.
I feel that we see this in shorts more often than I’d like. Ironically the ones that try to fly under the radar and make no distinct (and vulnerable) choices are actually the ones that stick out the worst. We can fix this problem by choosing shorts that were meant to be shorts.
Here’s some examples…
These have been gaining crazy momentum on the women’s side, but they’re just as good for us. I’m not talking some garbage from Lululemon, I’m talking some shorts with a little more retro flare. As they tend to be on the shorter side, I don’t wear them a ton while traveling or working - mainly for running errands and hanging out with friends.
They usually won’t be cotton, so maybe think of these as a potential replacement for the Patagonia Baggies you forgot about in the bottom of a drawer. Because they’re so short, I find they style well with long sleeves on top. Maybe a rugby or an oxford. I prefer sneakers or boat shoes with them and long socks.
Much like with sporty shorts, outdoors-y shorts feel intentional. There is a great form meets function here - and with a bit more volume and length, they’re a little easier to wear into uncertain terrain - like the actual outdoors.
The belted short feels so crucial because when you actually have stuff in your pockets, you feel a touch too vulnerable. (Another shot across the bow for my Patagonia Baggies.) The Gramicci G-Short is 100% cotton, comes in a bunch of colors and has two back pockets. (I hate only one back pocket.) They are fairly long. But they can be cuffed, hemmed, or chopped if needs be.
The built-in belt is fun, but not mandatory.
The greatest outdoor short grail of all is a pair of vintage Boy Scout shorts in a grown-up size. There are various iterations, but my favorite is the one with the little pockets on top of the big pockets. Yes, they are a cotton/poly blend, but that’s sometimes the price we pay with vintage. And I found a pair today in a size 34, so keep your eyes peeled! They exist!
The Boy Scout joints are clearly heavily inspired by military styles. So add any fatigue repro derivatives to this list. Big, functional, and hopefully breathable. Olives, khakis, and camos are all great options.
Cut-offs really helped me learn to love shorts again. We may have grown up with jorts as a never-nude punch-line, but I think many of us have come to love them. Nick Wooster himself condoned this practice on his recent appearance on Throwing Fits. His advice? Just make sure they’re super distressed.
Talk about intentional! The frayed edge draws a line in the sand and says, “hey, I’m wearing shorts, motherfucker.”
You can cut just about anything. You can chop old chinos, fatigues, work pants, trousers - really anything you have and don’t wear anymore. Sometimes a colorway that doesn’t work well in long pant form really thrives as a short! Or maybe those well-loved jeans have been patched one too many times and need to become jorts!
Hell, you can even cut shorts that are too long and fuddy-duddy into something a bit more cropped. I’ve talked about them a few times, but I have done this in the past with Ralph Lauren shorts that didn’t quite hit me where I wanted them to.
In no particular order - here are some of my favorite pants to see chopped…
Vintage work pants - Dickies, Ben Davis. Find a vintage pair that are too short for you and cut em into proper shorts.
The bigger Levi’s cuts - 555, 554, 550, 565 - basically anything that isn’t a 501 or 505 will work great. (Although even a 501 could be good if you’re on the slimmer side.) Black denim works great and feels a little more punk and a little less trailer trash.
Cords - there are so many vintage corduroys floating around and many of them aren’t quite right. Though we associate corduroy with Fall/Winter, historically many beach-y brands used corduroy for their summertime shorts. You can emulate that if you have a pair of long cords that just don’t get enough love.
Some things are classic for a reason. You very well may have all the shorts you could possibly need. The unimpeachable classics will always be good - Ralph Lauren Tyler Shorts, for example - so don’t sweat it if you feel you have your shorts rotation dialed.
I, for one, will never love my shorts as much as my long pants, but if we’re gonna be stuck wearing them for the next few months, we might as well get creative!
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