Five Ways To Wear One: Tailored Fit Shorts

by Beau Hayhoe  |  in Style Tips

Shorts used to be something that you threw on just to throw on. The default for a lot of us (myself included) until a few years ago was a pair of cargo shorts or something a little baggier.

They weren’t jeans, they weren’t dress pants, and they kept things cool… so they worked.

But shorts really have become so much more than a way to avoid overheating in the summer.

Shorts are certainly as versatile as a great pair of dark denim if you’re willing to push the boundaries of style a bit, and judging by the fact that we’re all here, I’d say you are!

Looking for the best shorts to buy now?

The Best Men’s Shorts For Summer

How should shorts fit? What are the best colors?

So that sets the stage — but what pair should you pick up?

In case you prefer video, I covered how shorts should fit, the best colors for your summer wardrobe, as well as what to wear with shorts in this video from the Effortless Gent YouTube channel.

By the way, if you haven’t subscribed yet, you can do so here!

The Tailored Fit Shorts

For guys of average to slightly taller heights, the inseam is going to be one of the first things you should look at when shopping around for a shorts upgrade.

For the majority of the population, a 7” inseam should work quite nicely — that hits above the knee by a fairly decent amount. If you’re on the taller side, designers are offering pairs with inseams that run between 9” and 11”.

For our purposes though, the goal would be to keep the shorts above the knee while keeping things tailored and clean — that means ditching the cargo pockets and extra fabric, yet keeping some coverage in the thigh area.

Flint and Tinder 365 Shorts

The Flint and Tinder 365 Shorts are cut like chinos, but stretch like a performance short. Available in several colors in 5", 7", and 9" lengths.

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Bonobos Stretch Washed Chino Shorts 2.0

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When it comes to the pair (or pairs) you should pick up, plenty of brands have been amping their short(s) game.

Bonobos produces washed chino shorts in a ton of different colors and inseam lengths running from 5” to 11” (stick to 7-9″ if you’re around average height).

J. Crew also offers terrific color options, from dusty blues to standard khaki options, and as part of its monthly collections.

Caring For Your Shorts

It tends to depend on what color of shorts you might pick up, but when sticking to neutral basics that are easily matchable (like navy, grey or a dusty khaki), the shorts should be machine-washed on a light cycle with like colors.

Hang-drying or tossing them in the dryer is up to you, although with something like a washed chino fabric, hang drying the shorts would likely extend their life by a good amount.

Ironing your shorts could be preferable for some as well, especially if you have a fabric that tends to wrinkle a bit (like the linen-blend shorts seen in these photos).

With care, color and fabric in mind, check out some ways to style your new shorts below.

1. Casual & Cool

five ways to wear one: tailored fit shorts

The first outfit seen here uses the slate blue color of these shorts to pair up with another earthy neutral — an olive henley.

The piece in question is made in America by Pistol Lake and features rugged details like unfinished sleeves and sturdy double-stitching throughout, so it’s just as ready to pair with crisp shorts as it is to wear under a shawl cardigan.

Other details like the striped webbing belt add a warm-weather, nautical touch. This could be a good opportunity to break out a classic watch with, say, a blue dial watch to play off the olive and slate-blue colors in the outfit.

2. An Evening Breeze

five ways to wear one: tailored fit shorts

With this second outfit, most of the pieces and the general styling stays the same. That’s the versatility of a great pair of shorts in a trimmer fit, and an ever-versatile pair of white sneakers.

This is the kind of outfit you throw on for a day strolling along the water or perhaps a casual dinner out — with a neutral-leaning pair of shorts, the sweater could be switched up, as well.

A light tan cardigan like this one from Club Monaco) would also work here) A simple brown leather watch hits the sweet spot between being crisp yet not overly dressy, as well.

3. A Pop of Print

five ways to wear one: tailored fit shorts

In addition to amping up its short game, Bonobos and other brands have gone wild this season with floral prints and other designs that really leap out at you — in a good way, though!

The print on the shirt seen in these pictures (and the print on the shirt linked to above) is a bit more subdued than that, but still complements the shorts nicely thanks to the solid navy base for that print. A braided leather belt is equally at home in the summer as in the fall & winter; it’s more casual than the standard dress belt, which fits more with laidback shorts.

The watch in this instance is up to you — a brown leather watch as mentioned above would work here, as would a neutral stainless steel diver or an even more minimal mesh watch (which designers seem to be doing more of these days).

4: Polished Prep

five ways to wear one: tailored fit shorts

For the fourth outfit on this list, we harken back to some prep-inspired style — a classic polo and shorts will put you in that territory for sure.

But this isn’t the country club version of that outfit — the fit on the polo and shorts is trim, while the leather loafers are a big upgrade over flip-flops.

Tucking the polo in would make things decidedly dressier, but if you do untuck the polo, just be sure the back tail doesn’t hang down too far. The brown leather watch from outfit #2 can definitely come in handy here, too.

5: Pushing The Boundaries

five ways to wear one: tailored fit shorts
  • Tailored shorts (similar)
  • Lightweight unconstructed blazer (similar)
  • Heather red pocket T-watch

Keep the worn-in red pocket T-shirt from the second outfit, toss in that same pair of slate-blue shorts and pair it all with … an unconstructed blazer? Let the debate begin.

While this is a decidedly more fashion-forward look, turn to style icons like Nick Wooster for tips on how to wear the blazer and shorts combo — the fit of both pieces is dialed in as much as a regular suit, and that makes things stick.

The fact that Wooster’s a style legend maybe means this shouldn’t be attempted by mortals. BUT the T-shirt in and of itself makes this less dressy and a little less fashionable — more laidback.

Could this outfit work everywhere and for everyone? Not necessarily; it’s got a bit of an upscale patio/outdoor dinner party feel to it. If the blazer strikes you as too strange or it gets too hot, you could always ditch it — in which case you’d be left with a look a little bit more similar to outfit #4.


If you’re just getting hip to the possibilities that shorts can bring, best hurry up — summer’s practically here.

With a little imagination and the willingness to try a new combo or two, they can definitely be every bit as versatile as those chinos or dark denim you always reach for.

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