Summer Men's Shoe Guide: Footwear & Fashion for Every Occasion

Sep 25, 2023

Cormac Newman August 2, 2023

With every change in season comes a fresh batch of footwear, so here we are, ready to take a crack at the newest, latest, and greatest from our favourite brands. Thanks to summer’s warm breeze and sunshine stretching into the evening, social calendars practically fill themselves with al fresco activities. Beachside barbecues and patio parties reward garden-variety chores like pruning the trees and mowing the lawn. A full spread of events requires a deep closet to keep your fits current (alongside some serious social stamina).

No matter the occasion, the right pair of kicks should tie your look together with a fashionable edge — even when the look in question is just a swimsuit. From versatile tennis shoes to classy leather loafers, we’ve de-mystified four types of shoes, explaining how to style and where to wear. Plus, we’ve made a few recs for inspiration, whether you’re aiming for quiet luxury or nightclub flashy.

Business Casual is an actual dress code, but its footwear regulations are still subject to scrutiny — some allow sneakers, while others say these gatherings should strictly adhere to loafers and lace-up dress shoes. We examined both sides of the debate before making our selects, so we can safely say that we’ve got both camps covered. From derby shoes and penny loafers to chukka boots, these picks fit the bill for all your ‘classier than average, but not quite black tie’ needs.

Crafted from soft suede leather, this pair takes on a classic silhouette that’s formal, yet understated. Light beige leather makes a subtle pop against the shoes’ grounding, earthy brown soles. The easygoing palette works well with a range of looks, from preppy pastels on the weekend to business-casual fits in the office. If that’s not enough for you, these penny loafers boast a lightweight feel that won’t overheat on long days in the sun. ($1,195)

On Running launched their third tennis-inspired sneaker as part of a co-collection in men’s shoes with Swiss tennis player Roger Federer. They might be classified as a sneaker, but these kicks are billed as an item for everyday apparel, with a classic cut fit for anything. CloudTec® elements make the interior plush as a sock, while matte vegan leather sponsors the shoes’ ethically-sourced, understated style. ($179)

Derby shoes are as close to one-stop shopping as it gets in footwear; they’re right at home in the workplace, at a party, or even a summer wedding. Louis Vuitton’s Minister Derby design is sleek and chic — an elegant, chiseled outline and platform heel command attention. Towards the back, a textured checker pattern adds an edge of sophistication to your look. ($1,250)

Did you know sneakers, tennis shoes, trainers, and even “plimsolls” all refer to the same shoe? Like soda, (or Coke or pop, if that’s your style) the sneaker has reached the level of cultural ubiquity that begets a family worth of regional nicknames. Strong accents aside, these shoes have a wide range of functions: they’re the footwear of choice for skaters and track stars, as well as a status symbol for collectors of high-end hype, and — perhaps most importantly — a staple in casual wear for all ages. If you’re looking for a versatile addition to your shoe rack, it’s best to go with a neutral shade that pairs with all outfits. If it’s novelty you’re after, though, there’s no shortage of sneakers with fluorescent patterns and embossed designs guaranteed to draw attention.

It’s often said that you can’t be everything to everyone, but Fendi Flow sneakers come pretty close. They’re fashion-forward, with grey-brown scales climbing around the shoe’s sharp edges, yet their subdued palette means they match a wide range of outfits. Cutting sleek silhouette, this pair adds a definite spring to your step without being confined to the workout realm; they’re just as comfortable with street style looks. ($1,850)

Leather and mesh are an unlikely combo, for sure, but after seeing these kicks, we’re thinking they should team up more often. While they stick to the well-trodden territory of black, beige, white, and brown, these shoes are far from a snooze — the interplay between their embossed logo, white mesh, and leather make a textured display of design prowess. ($1,090)

This season’s offerings show that high-tops are officially back. Prada-logo straps lock into a futuristic body, complete with bold lines and structured heels. Painted like a cityscape, these sneakers shimmer like neon lights in a nightclub with just the right amount of eye-catching flash. ($1,590)

On the Sprint Runner’s surface, smooth leather transforms into an iridescent canvas. Colours splash against the silvery leather like graffiti, reflecting a technicolour design suited to a life of nightclubs and streetwear. ($1,190)

Sandals have been around for just over 10,000 years — humans put together the first known pair around the same time we domesticated cattle and cultivated wheat. That’s to say, we’ve had a long time to perfect the craft. The ultra-simple, original style consists of a leather sole tied together with straps over the foot and ankle. Some modern looks have pared this down further with single-strapped ‘slides,’ while others use innovative fabrics to construct a contemporary design. We’ve selected four designer picks to sample the full spread of beach-ready styles.

Simple designs endure for a reason: these sandals capture the sunny ease of summertime with their fresh, pale colour scheme and twin-touch straps. Plush outsoles add a breezy bounce to the step thanks to their source material, EVA — a polymer-based material blend. ($138)

Knitwear straps meet rubber soles in this vibrant, patio-ready pair of slides from SWIMS. They were designed to maximize traction, ensuring that long walks on the beach don’t include a tumble on the jetty. A casual slip-on style makes them an easy pair to slide into weekender bags for a quick getaway. ($158 at Harry Rosen)

Louis Vuitton’s Panama Sandal practically glows with icy-blue accents. The shoe’s soft, anatomic insole and micro outsole ensure comfort and reliability, while a monogrammed top strap adds textured details. ($1,290)

Graduations, weddings, your friend who takes their birthday a tad too seriously — all of these occasions call for a formal dress code. If you’re looking for shoes to match your black tie, you’ve come to the right place. We recommend investing in a classic pair of patent black leather shoes to match with almost any suit. Shiny leather loafers, silver buckles, and sleek-cut silhouettes are hallmarks of a good formal dress shoe.

Prada shows exposed laces in their classiest incarnation, tucked into the polished leather body of these Oxford shoes. Elevated outsoles boost height and draw attention to the shoe’s contour, which makes a sleek taper down to the toes. In a nutshell, these shoes are the white tablecloth dinner of footwear: a sophisticated take on essentials. ($1,350)

Palladium-plated Kelly buckles glimmer against the deep black calfskin of these Hermès Destin Loafers. They sport a warm, orange-leather sole for a lively flash against the luxurious onyx exterior. Rounding out at the toe, they’re comfortable being the best-dressed in the room. ($1,625)

To finish off our list, we chose the Timeless Loafer from Dior. It’s a truly classic design (as the name would suggest), with a Dior signature embossed on the shiny leather vamp. Plus, its Blake-construction leather sole boasts a non-slip detail. Bold, sharp, and polished to perfection, these loafers pair with any suit. ($1,300)

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