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A man’s guide to pairing shoes with shorts

Shorts are a paradox. For one, their reputation as casual-wear is agreed on by the universal socio-cultural dress code. Clubs and restaurants the world over ban shorts. Strict offices don’t approve trouser hems shorter than a capri, even on dress-down Fridays. American cultural critic Fran Lebowitz infamously declared in 2015 that she’d rather “see someone coming toward me with a hand grenade” than seeing grown men in shorts.

The European leg of last month’s men’s Spring 2019 shows, then, would have detonated the world’s Lebowitzs. Its catwalks and the cobblestone streets were teemed with shorts. Emerging out of the ether into sudden cult item stardom, they were donned by every member of men’s fashion in-the-knows — buyers, editors, stylists and celebs who jet set through Milan and Paris Fashion Week. They’ve become more than just a means for warm-weather ventilation.

They’re hard to pin down, we know. But as seen through shorts-swamped street galleries, the key not to infantilise the faux pas-prone summer staple is anchored to your footwear. So be it for a weekend lounge by the pool or a smart-casual business meeting, here, we guide you through five fail-proof footwear styles to underpin your shorts with.

shoes for shorts sneakers


What they are: Once exclusive to performance-wear, sneakers have now become a mammoth millennial-magnetising business of their own. Visual inspiration on pairing sneakers with shorts run as rampant as the types of sneakers that are available these days — from old-schools such as low-top Chuck Taylors to 2018-apt chunky ugly dad shoes in the veins of Balenciaga’s Triple S.

How to wear: To go classic, throw on slim-cut all-white sneakers with chinos or faded denim shorts. When selecting denim shorts, remember that they’re most flattering when tailored to fit closer to the leg — but not so tight as to constrict the thighs — and end just above the knees. If you prefer to test the trend currents, look no further from Spring 2019’s street style looks. Exhibit A: Luka Sabbat attended Virgil Abloh’s Louis Vuitton menswear debut show in the new LV cargo shorts, cinched with an equally utilitarian belt, with low-top sneakers and black socks pulled high.

Pro tip: As hemlines ride high, you may want to balance the amount of skin exposure and pull socks high. This works best with chunkier silhouettes. If the street-favoured manoeuvre doesn’t suit you, stay safe with ankle-length or invisible socks. For a sockless alternative, go ahead and knock yourself out with snockers.


shoes for shorts espadrilles


What they are: Way long before Pitti Uomo gents dubbed espadrilles as their footwear of choice, they were born on the feet of Spanish warriors. Which explains why the structure of these hand-woven slip-ons are sturdier than they seem. Their cotton fabric makes them lightweight while the traditional, natural rope soles enable a breathability and freshness — making for the ultimate choice in balmy climes.

How to wear: Synonymous with a certain kind of Mediterranean summer, channel Jude Law’s raffish Dickie Greenleaf yacht day out in The Talented Mr. Ripley. Wear the louche-chic espadrilles with sophisticated pleated shorts and a billowing camp-collar white shirt. Taking up so little space and weight, throw a pair in your car, your gym bag, or your weekend bag. Basically, anywhere you might enjoy the option to free your feet is where they belong.

Pro tip: Espadrilles should be worn without socks. Still, sweaty feet are never a good thing. Prior to slipping them on, make sure your clean feet are completely dry and then lightly sprinkle them with talcum powder. You’ll thank us later.


shorts sandals


What they are: When we say “sandals”, we’re not talking dusty toe-thong flip flops. But rather, the new-wave species the likes of Louis Vuitton’s Honolulu slides, Rick Owens’ Birkenstocks, Prada’s Cloudbust iterations and maybe cult Japanese label Suicoke’s velcro-strapped slip-ons. Like sneakers, sandals are the season’s breakout commodity, with design gods chipping in their own takes on the summertime kicks.

How to wear: Sandals, regardless of hefty design god price tags, are made for laidback days. For an optimum no-emails-today look, cargo shorts in linen blend work brilliantly with Birkenstock-style sandals. For sun-dappled beach days, skimp more on length and have a go at short shorts or jorts (a.k.a. jean shorts). For smooth air travel to your holiday destination, easy slides are your trusty go-tos along with Orlebar Brown’s tailored swim shorts for a seamless airport-to-pool transition.

Pro tip: To sock or not to sock? Let’s be real, it’s 2018: the veto for sock-and-sandal combo is outdated. Wear socks if you like, live out your best scumbro life. But if you’re going out sans socks, consider a pedicure to trim unkempt nails. And if a drive is part of your schedule for the day, try a pair with a back strap so your feet don’t slip off the pedals.


shoes for shorts
Boat shoes.


What they are: Created by Paul Sperry in 1935 when he cut siping — a series of narrow slits — into the rubber soles of his shoes, early renditions of boat shoes were designed to prevent sailors from slipping on a wet deck. These days, his nautical top-siders are as ubiquitous on dry land.

How to wear: Boat shoes look best when they’re plush iterations of the OG Sperry Top-Sider. Think: neutral-hued leather, moccasin-style uppers with rugged laces and, of course, slip-proof rubber soles. They work great when kept casual, and at most, preppy. Complement them with loose-cut, above-the-knee linen shorts to keep you breezy. Then maybe try experimenting with a pair of salmon pink shorts or a striped polo shirt. Surprise yourself.

Pro tip: Designed to be kicked on and off whenever needed, go sockless in your boat shoes. Lightly sprinkle clean, dry feet with talcum powder before putting them on. Otherwise, invisible socks are the way to go.


shorts derbies


What they are: Thanks to their versatility, derbies — known for having its eyelets sewn to the outside of the shoe’s upper giving them their distinctive open laces — are the do-no-wrong dress shoe classic.

How to wear: Nailing the casual-formal look is never an easy feat. The advent of city shorts may complicate it more but here’s where lace-ups come in. Opt for rubber-soled brown brogues, styles in woven burnished leather. Take note that black oxfords rarely complement bare legs. As for your shorts, look toward your suits rather than your swim trunks. They should be tailored to the leg with a length that finishes slightly higher above the knee. Tucked-in long-sleeve shirts and blousons work splendid, but for a more formal look, have a blazer or suit jacket in the mix.

Pro tip: Secret socks or fine lisle ankle socks in a light colour are preferable for that extra formal slant. Be mindful not to tie your laces too tightly as the feet tend to swell during the day.

(Illustrations: Nadine Christmas)

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