Top 10 Footwear Picks for Perfectly Pairing with Shorts

Top 10 Footwear Picks for Perfectly Pairing with Shorts

When it comes to men’s wardrobe staples, shorts are at the top of the list since they are both fashionable and functional. Most guys like the versatility of these garments, but it can be difficult to find the right shoes to go with shorts. Finding the right pair of shorts and shoes that complement each other and your individual sense of style is essential when putting together an outfit. Numerous shoe types work well with shorts, whether you’re going for a dressy look for a summer date or a laid-back one for a vacation.

Some guys like a more relaxed look by wearing sneakers or espadrilles with cargo shorts and a polo shirt, while others go for a more put-together vibe by pairing chino shorts with a button-down shirt and loafers or boat shoes. Choosing the right shoes to go with shorts might be difficult because there are so many options.

We hope our guide to the best shoes to wear with shorts will serve as a source of inspiration. Learn the many ways in which men can pair their shorts with a variety of shoes, from high-top sneakers to loafers and formal shoes.

Typical Sneakers

When worn together, shorts and casual shoes can create a laid-back yet stylish look. It’s important to keep your outfit looking current and fashionable while pairing casual men’s shoes like sneakers, trainers, espadrilles, and more.Men's ankle sneakers white street style apparel shoot

Wearing athletic shoes with jogging shorts creates a casual yet current appearance that may be topped off with a designer tee, black Havana hat, and trendy sunglasses. This trendy streetwear outfit is perfect for a day at the beach or a brunch with the girls. For an alternative that is both elegant and seductive, try pairing trendy shoes with khaki shorts, a light woven henley shirt, and a sports watch.

Canvas slip-on shoes are both trendy and versatile; they look well with a wide variety of shorts, including denim, khaki, and chino. If worn properly, men can look suave and put together by keeping the hem of these textured shorts at or above the knee. It’s acceptable to wear the shorts a little higher, or even roll up the bottoms, if you have a strong build. Chino shorts, a button-down shirt, a casual blazer, and loafers are a statement-making outfit.

Fashionable guys can choose from a wide variety of casual men’s footwear, including wool runners, low-top leather sneakers, slide sandals, and chukka boots.

Elegant Everyday Shoes

Put together a polished and attractive look by adding a pair of elegant casual shoes to your shorts. Investing in high-quality smart footwear, such as loafers, suede Oxfords, dress sneakers, and leather boat shoes, is crucial to achieving a wonderful style. Modern gentlemen can also look for shorts that exude an impression of cool, casual style.

Combining leather sneakers, loafers, or Oxford shoes with navy, khaki, or white chino shorts, a woven belt, button-down shirt, and designer sports watch will give you the ultimate debonair style. Add a blazer to dress it up, or go casual with boat shoes and a polo shirt.

Nubuck upper loafers with black leather outsoles are a classic choice that will never go out of style. Focusing on clean silhouettes and form-hugging cuts creates the sharp, modern look that today’s most dapper men covet. Smart casual shoes with shorts are a popular choice among trend-conscious men because of their versatility and modern aesthetic.

Shoes for the Office

Dress shoes and shorts make a great combination because they are both semi-formal and comfortable to wear in the warm weather of summer and spring. Impressively sophisticated and fashionable, you wear a subtle cuff with your dress shorts and pair them with a dark pair of leather Oxford shoes.Elegant, used brown leather male shoes set on a brown wooden table

Dark navy dress shorts together with brown dress shoes add to an exclusive and dignified ambiance, while black shorts and glossy black leather shoes produce a powerful and daring style. When combined with well-tailored designer shorts, brogues add a sense of class and sophistication to any outfit.

Men can stay cool and stylish in the summer by pairing khaki or chino shorts with a pair of walnut-colored monk strap dress shoes. Add a lightweight button-down shirt that isn’t tucked in for a polished yet relaxed look. Choose a button-down shirt with banker stripes to look authoritative and polished.

These stylish looks would be incomplete without a stainless steel sports watch or a leather-strapped dress watch. Always double check the dress code before heading out to a high-end event or location, even if you know that wearing dress shoes with shorts is the epitome of elegance and modernity.

Sporting Gear

Men who care about their appearance should have a pair of athletic shoes in their closet because they are the most adaptable shoes for wearing with shorts. Wearing athletic shoes with shorts helps generate a timeless and young look, whether you’re going for a modern athleisure vibe or urban sleekness. For a more contemporary gym style that works for brunch, some men may choose to pair wool athletic shoes with running shorts or form-fitting performance shorts. Some people prefer the casual look achieved by pairing chino shorts with a t-shirt or button-down shirt and low-top leather designer shoes.

Many guys like to pair trendy shoes with khaki shorts, a polo shirt, and a sports wristwatch to project an image of strength, virility, and style. Popular contemporary labels like Allbirds, Madewell, and Atoms provide basic runners in eye-catching hues that are both fashionable and functional.

Brands like Nike and Adidas have stood the test of time because they are dependable and adaptable, allowing for both athletic and fashionable wear. Dunks or Stan Smiths are great options for men to wear with a solid-colored tee and shorts. This outfit is both one-of-a-kind and laid-back, finding the sweet spot between athletic and urban chic.

A safe outfit combination is form-fitting shorts, a crew-neck t-shirt, and low-top white leather athletic shoes. Men who care about their footwear collections will shop for limited edition styles from luxury labels like Prada, McQueen, Balenciaga, and the aforementioned Oliver Cabell, M.Gemi, and Common Projects.

Easy-On Slippers

Various models of men’s slip-on shoes are appropriate to wear with shorts because of the way they project an air of maturity and masculinity. Slip-on shoes, shorts, and a t-shirt make for a casual summer attire, while chino shorts, a button-down shirt, and a blazer are appropriate for more formal events.Slippers on a carpet at the entrance with shallow depth of field

Consider penny slip-ons, tassel slip-ons, or sumptuous bit slip-ons when putting together your outfit; they all have a sleek design and a flattering ankle cutout. Slip-on shoes with a leather bit and dress shorts give off an air of refined sophistication. Gucci’s horsebit slip-ons are a timeless classic and an essential to any wardrobe.

Shoes with a Heel Lift

Putting on high-top sneakers with shorts is a daring move that is sure to get you noticed. With the appropriate style decisions, these young, casual shoes may be incorporated into fashionable ensembles. High tops and shorts can be customized to fit your individual style, whether you choose to wear them with khaki cargo shorts and tees or black chino shorts and sweaters.

You can’t go wrong with a pair of timeless high-top shoes from a legendary label like Converse, Vans, Nike, or Adidas. Put on some canvas shorts and a bomber jacket, and your Chuck Taylors will be the most stylish part of your streetwear ensemble. Put together a cool throwback look by pairing your Chucks with some denim shorts and a tucked-in raglan tee.

White canvas high tops are great for the late summer and early fall when worn with black shorts, long socks, and a sweater. Fitted chino shorts, suede high tops, and a button-down shirt are another option for a more refined look.

Luxury brands like Gucci and Prada create exquisite footwear for the fearless and trendy, while brands like Beckett Simonon and Koio produce unique leather-crafted hybrid high tops that work well with smart casual clothes. Try out a few different brands and styles before settling on the perfect pair of high-top sneakers.

Shoes for the Sea

When paired with shorts, boat shoes can be worn as part of a variety of different ensembles, from casual to business casual. Choose boat shoes that complement your outfit by adding a sophisticated touch for a commanding weekend look or a casually elegant flare for a stylishly laid-back ambiance.Boat shoes of our punting tour guide and professional punter in the pier in Cambridge, UK

Consider pairing fitted chino shorts with a dress shirt and leather boat shoes in a neutral color for a dapper look. Choose a sophisticated casual summer look with brown leather boat shoes, a white polo shirt, and slim-fit chino shorts for a stroll around New York City or a day at the beach in Los Angeles.

Classic style is best exemplified by a pair of boat shoes in a dark brown, tan, slate, navy, or beige color. Put your money into a pair of shoes in a bold summer color to make your outfit pop.

Traditional Brogues

When it comes to putting together a dapper and memorable outfit, brogues are the way to go when you’re wearing shorts. This attractive shoe type adds flair to your outfit but only when paired with high-end fitted dress shorts. There are a wide variety of brogue shoe designs to choose from, including the open-laced Derby and the closed-laced Oxford. Dress shoes might have full or wingtip perforations, half perforations, or quarter perforations.

Wear a straw trilby hat and a shirt made of modest, lightweight fabric like linen in the summer. Pair your brogues with seersucker and finish off the look with a high-quality crew neck t-shirt or a warm polo shirt for that Ivy League preppy look. When going for a sophisticated casual look, a pair of brogues is a great shoe choice to wear with a pair of shorts and a button-down shirt.

Everyday Sandals

Sandals are the quintessential casual shoe for men to wear with shorts, thanks to their breezy and unfussy aesthetic. Find some sandals or open-toed shoes that go well with your shorts for a day at the beach, lake, or summer pool party. While some guys may prefer flip-flops, we recommend that you consider a pair of leather sandals by a trusted brand, such Birkenstock or Grenson. In addition to creative sandals like leather mules and huaraches, the Birkenstock fashion trend goes nicely with utility shorts and light-colored linen shorts.Man's feet sit on rocks above road near ocean. Intentionally glare

Sandals in deep brown tones, such as tobacco or java, are a great choice for a manly look. You can match your flip-flops to your swim trunks or a casual shirt. Consider investing in a long-lasting pair of chic flip-flops, like the Olukai leathers or the Prada brushed sandals, for a more put-together look.

Fabulous Espadrilles

Men who want to dress casually but yet look good should pair espadrilles with shorts. In addition to being a summer staple, espadrilles’ classic rope soles add a stylish textural element to any casual or dressy off-duty ensemble. The uppers of espadrilles can be made of cotton for a more casual look or canvas for a more minimalist, laid-back feel. These shoes are a must-have for any fashion-forward man’s closet because of the many ways they can be paired with shorts.

Wearing espadrilles with chino shorts gives men a neat and cool style that works for anything from a stroll along the boardwalk to a lunch date or a music festival. Add a t-shirt if you’re going for a cute, simple look; a fitted polo shirt if you’re going for a sophisticated vibe; or a button-down shirt if you’re going for a laid-back vibe. Wearing a linen blazer will take your outfit to the next level. You can’t have too many pairs of espadrilles, as they are one of the most ubiquitous types of casual footwear for guys.


Men can seem dapper and rugged by wearing shorts with boots. There are a broad number of boot styles and designs to choose from, despite the fact that boots and shorts go together naturally. For a more rugged, manly look, some guys choose suede chukkas or work boots, while others like leather Chelseas or combat boots.

When paired with military or khaki shorts, a hunting vest, and a tan utility jacket, crepe sole desert boots add a sophisticated touch to casual attire. A field watch, like a Hamilton Khaki Field or a Rolex Explorer II, completes this well-balanced getup.Men fashion in leather boots, Close up view on man's legs in gray jeans and yellow leather boots.

Putting on a pair of cargo shorts, some work boots like tan Timberlands, and a t-shirt is a great way to show off your style and taste in streetwear. You may also go for a pair of white shorts and a blue cardigan while wearing white suede chukka boots. To achieve this style, make sure the top and bottom cardigan buttons are undone for a tidy and masculine appearance.

Men looking to make a bold fashion statement can’t go wrong with a pair of suede Chelsea boots in a deep brown or black. Leather Chelsea boots, shorts, and a button-down shirt make for a sharp casual ensemble, or you can dress things up with a short suit. While this may be too daring for some, those with an eye for style will relish the chance to turn heads wherever they go.