2017 is the year I attempt to complicate shorts.
For years I have been an adamant follower of the rule that men in shorts must dwell at a length above the knee only to find that the results can be repetitive or wannabe youthful when indulged too frequently. If you, like me, are a lover of shorts and only wear them, you know that variety is needed. Not just in material but in style. You have to do more than just wear one “type.”
To that, I’ve gone on a quest to understand longer shorts particularly as they relate to Winter wearing. I dipped a toe into this pool in 2015 after securing a pair of baggy vegan leather shorts and some long Ami shorts in the hopes of trying something different. What I found is that these shorts are perfect for cooler weather (Duh.) and add something surprising to your style.
As if you need to be reminded of this, this look is very nineties and streetwear adjacent. This means there are simultaneously more rules and less rules as these shorts require so little yet so much to pull off. Long shorts can easily look sloppy but, when placed in the right context, you’ll look great. Thus, here are some tips for embracing long shorts, particularly in Winter.
Go For Volume
Length is one thing but you don’t want the shorts to hug the body or you’re going to look like a European dad lost on vacation. You need some bagginess outward instead of downward. You don’t want to go drop-crotch but you do want to to fan out some, to illustrate that these are indeed shorts—not wannabe pants. An example: the TOMORROWLAND Twill Pleated-Front Shorts, which offer room via interesting fabrication. No, they are not parachute shorts nor are they super skinny but they feel like they could be dress pants missing their bottoms.
You always want these shorts to fall from mid-calf to low knee. No higher (Otherwise, go for shorter shorts.) and no lower (Just wear pants.). Pair them with high socks and you’re all set. A good example of these are Marques Almeida Blue Denim Tracksuit Shorts which I love save for the elastic waist. More on that later.
This is the secret to long shorts: a pleat. They add volume and interest while taking otherwise drab bottoms and turning them into something of note. Unlike shorter shorts, long shorts require heavier fabrics and interesting execution over pattern, texture, and the shock of male leg: the key to long shorts is that they are understated. Pleats add intrigue by doing very little. The best example are these Sunnei Denim Shorts that double as both dressed up shorts and dressed down jeans all because of the pleat.
Be The Big Pattern
If you must pattern, the pattern has to be big otherwise you will look like wallpaper. Because these shorts occupy more fabric retail space, you need a pattern that can stand up to that by being bigger. This is a tricky one and, if you don’t feel comfortable playing here, don’t. See these PATH Printed Silk Shorts for an idea or the Ami ones I own. Everything should be exaggerated with long shorts, even things like patterns and textiles.
Don’t Forget Your Ass
The biggest risk of long shorts is that you forget to make your ass look good. Shorts are all about that donk! Don’t skimp on it, dudes, falling prey to the dreaded doodie butt. Don’t know what that is? Look at the Acne Allan Shorts from behind. The big, low pockets on the butt make you look like a baby that needs their diaper changed only exaggerated by the shorts’ longer length. That is not a good look. Elastic and draw string shorts also add a risk of doodie butt since they aren’t very securely fastened to you and will droop as the day goes by. Thus, go for a classic waist (i.e., can be belted) with smaller pockets that lie higher on the rear. Anything lower, bigger, and wasitless will leave you looking like a baby. For an example of a simple, ass loving short, use the Givenchy Blue Cotton Bermuda Shorts for reference.