A Guide for Wearing Shorts Like an Adult

Light twill shorts, $125 by Norse Projects;
Patchwork lobby shorts, $150 by Alex Mill

Alex Mill Patchwork Lobby Shorts

Light twill shorts,
$125 by Norse Projects

A Guide for Wearing Shorts Like an Adult

About five years ago, I stopped wearing pants. No, this was not an adoption of an awkward fashion Porky Piggin' but instead a shift from long pants to short pants. The move came from a few different directions. First, I noticed that so many people had a reaction. They lob compliments at you from every direction—on how fit your legs are and how nice it is to see a little uncovered man leg. Second, it was a fashionable political statement of alternative sexuality and gender to rebel against the assumption that real men "have to wear pants." Third, I live in perennially pleasant Los Angeles.

But this sartorial move hasn't been an easy feat. And I often get questioned about it from other men who hope to wear shorts more often but are concerned that they'll look too casual, unfashionably taboo, like Obama on a day off, or worse, a little boy who's been dressed by his mother. Shorts aren't always easy to pull off, so I hope I can impart some information on wearing them well given my years of not wearing long pants.

Norse Projects Light Twill Shorts

Patchwork lobby shorts,
$150 by Alex Mill

Generally, abide by the
three finger rule.

J.Crew Seeded Cotton Shorts

Seeded cotton shorts, $69.50 by J.Crew

The length of your shorts is key. Your shorts should always fall above the knee, landing somewhere between above the kneecap to mid-thigh. If you're questioning where exactly this is, go with three fingers' distance above the kneecap. Shorts are about creating the illusion of long legs and making you seem taller. When shorts fall below the knee, you look like a compacted little boy. When shorts rise so high they're at the crotch, you look like a mass of gangling pubes. The just-above-the-knee to mid-thigh range mitigates either extreme.

J.Crew Seeded Cotton Shorts

Seeded cotton shorts, $69.50 by J.Crew

Vans Authentic Shorts

Authentic shorts, $39.50 by Vans

Good shorts sometimes
require a good tailor.

Any pair of pants can be a good pair of shorts—if you have someone who can reshape the clothing item for you. This is why you need a good tailor which, if you read Valet., is something you already know about. A tailor can adjust the length of your shorts to the appropriate level, fashion any pair of pants into perfect shorts, and adjust off-the-rack purchases to look a bit more polished by taking out volume. Nervous about your tailor botching an item composed of such little material? Bring a favored pair of shorts as a model: this can guide them in terms of finishing details and the fit you like.

Vans Authentic Shorts

Authentic shorts, $39.50 by Vans

Wood Wood Chino Tomi Shorts

Chino Tomi shorts,
$170 by Wood Wood

Proportion is key.

Where shorts go wrong on people, turning them into unprofessional giant children, is the lack of proportionality. You want your shirt to fall right at the waist but no lower than the end of your front pocket's opening. This is why camp collar shirts are perfect for shorts: they land right at the waist. Low top shoes are optimal for the same reason, as they too add to the lengthening effect of shorts. Jackets and sweaters follow the same rule as shirts but with a stricter need to fall at the belt-line since these tops can be so puffy they can throw off your fashion-y feng shui.

Proportion is key.

Where shorts go wrong on people, turning them into unprofessional giant children, is the lack of proportionality. You want your shirt to fall right at the waist but no lower than the end of your front pocket's opening. This is why camp collar shirts are perfect for shorts: they land right at the waist. Low top shoes are optimal for the same reason, as they too add to the lengthening effect of shorts. Jackets and sweaters follow the same rule as shirts but with a stricter need to fall at the belt-line since these tops can be so puffy they can throw off your fashion-y feng shui.

Club Monaco Striped Shorts

Striped shorts,
$89.50 by Club Monaco

Wood Wood Chino Tomi Shorts

Chino Tomi shorts,
$170 by Wood Wood

Club Monaco Striped Shorts

Striped shorts,
$89.50 by Club Monaco

Apolis Transition Scout Shorts

Transition scout shorts, $78 by Apolis

Beware: bad pockets
make you look fat.

Why are cargo shorts an emphatic "no" in style circles? Because they make you look fat and sloppy, ballooning your thighs and rear with airy pockets. This isn't to say shorts with extra pockets are all bad (these from Apolis, for example, are pretty great). But know that any short with an exterior pocket or flap will add volume. Remember: shorts are a means to display long, athletic legs. A bulky exoskeleton of pockets distracts from this.

Apolis Transition Scout Shorts

Transition scout shorts, $78 by Apolis

Officine Generale Cotton/Linen Cuffed Shorts

Cotton/linen cuffed shorts,
$240 by Officine Generale

Similarly, pleats and cuffing
are for advanced wearers.

Once you master the basics, you can experiment with different forms and finishes. Pleats and cuffs are great examples of this since both, when done improperly, add the same bulk flapped pockets give. Pleated shorts should be tapered closer to the body if they fall closer to the knee or be a touch more voluminous if the shorts are shorter as to not create a bloomer effect. Cuffing works better on shorts that are shorter and wider because they add an official "cap" to the end of the hem. Longer, just above-the-knee cuffed shorts don't work as well since they enable a shrunken and stubby look.

Similarly, pleats and cuffing
are for advanced wearers.

Once you master the basics, you can experiment with different forms and finishes. Pleats and cuffs are great examples of this since both, when done improperly, add the same bulk flapped pockets give. Pleated shorts should be tapered closer to the body if they fall closer to the knee or be a touch more voluminous if the shorts are shorter as to not create a bloomer effect. Cuffing works better on shorts that are shorter and wider because they add an official "cap" to the end of the hem. Longer, just above-the-knee cuffed shorts don't work as well since they enable a shrunken and stubby look.

Saturdays NYC Double-Pleated Shorts

Double-pleated shorts,
$135 by Saturdays NYC

Officine Generale Cotton/Linen Cuffed Shorts

Cotton/linen cuffed shorts,
$240 by Officine Generale

Saturdays NYC Double-Pleated Shorts

Double-pleated shorts,
$135 by Saturdays NYC

Test drive before diving in.

The biggest rule of shorts is confidence. This is especially true when attempting to wear shorts to places that men-in-shorts are seen as taboo like work, evening functions or even more serious gatherings like a graduation or religious service. From experience, you can wear shorts to any event (I've literally worn a shorts suit to a funeral. My family demanded that of me, actually) once you're recognized as "a man who looks nice and professional in shorts." To accomplish this, test drive the look over the weekend when going out. Get them dressier and dressier, experiment and play, and then try them out on a Friday in the office. Once you do this enough, you can pepper in a shorts outfit during the week pending a good reception. And if someone asks, say what I always say: it's a political statement of equality, that any person should be able to display leg if they do not look overly casual. It never fails.