Shorts are great choices for men as well as casual wear on vacation.
Some men will wear casual shoes like trainers and espadrilles with cargo shorts and a polo shirt for a casual look, while others may prefer dressier footwear like loafers and boat shoes with chino shorts and a button-down shirt for a smart classy look.
Weve compiled a list of the best shoes to wear with shorts to inspire you with ideas. From sneakers and high tops to loafers and dress shoes, explore the many ways to style men's shoes with shorts for a stylish look.
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Shorts as Mens Shoes To Wear
If you want to achieve the desired look, you can wear casual shoes with shorts. Trainers, sneakers, espadrilles, and other casual mens footwear are all important.
For a chic and contemporary look, you can pair athletic footwear with shorts or sneakers with jogging shorts, and finish the ensemble off with a designer t-shirt, a black Havana hat, and cool sunglasses.
Canvas slip-on footwear is perfect with denim, khaki, and chino-style shorts. Guys can get that sharp, clean-cut finish by ensuring these textured shorts land right above your knee for an easy attractive look. Try chino shorts, a button-down shirt, or casual loafers.
Trendy guys will experiment with contemporary footwear like wool runners, low-profile leather sneakers, slide sandals, and chukka boots when it comes to casual mens footwear.
Wearing smart casual shoes with shorts will give you a classy and stylish look that will stand out. These include loafers, suede Oxfords, dress sneakers, and leather boat shoes. Modern gentlemen will also need to choose shorts that look effortlessly chic and exude style.
Combine leather sneakers, loafers, or Oxford shoes with navy, khaki, or white chino shorts, a braided belt, button-down shirt, and designer sports watch for a dapper look. Alternately, wear boat shoes and a polo shirt.
Classic and stylish, nubuck loafers with dark leather outsoles pair well with dress shorts. Keeping things clean and close-to-foot fits will give you the fresh, stylish look that fashion-conscious men desire.
Dress shorts with shorts are ideal for outdoor summer events or spring weddings that require you to wear semi-formal attire. You can style your dress shorts with a subtle cuff then pair your bottoms with dark leather Oxford shoes.
Black shorts and polished black leather shoes add a strong and dignified appearance, while dark navy dress shorts and brown dress shoes add a distinguished and dignified appearance to any outfit. This shoe style works well when worn with tailored designer shorts.
On hot summer days, guys can pair walnut-colored monk strap dress shoes with khaki or chino shorts. Complete these outfits off with a light and untucked button-down shirt. Or you can wear a banker-striped button-down shirt to give an impactful and sharp appearance.
For these chic outfits, a stainless-steel sports watch or leather-strapped dress watch is essential. While dress shoes with shorts are always elegant and modern, remember to always check out the dress codes for exclusive events and venues.
For stylish men who want versatile footwear with shorts, wearing sneakers with shorts can help create a timeless and youthful appearance. Others may wear low-profile leather designer sneakers with chino shorts and a button-down shirt for a casual look.
Many men will wear on-trend shoes with khaki shorts, a polo, and an athletic watch for a rugged, masculine, and stylish appearance. Popular modern brands like Allbirds, Madewell, and Atoms offer basic runners in trendy eye-catching colors.
Classic brands like Nike and Adidas are proven to be effective and versatile, allowing you to style them either athletically or stylishly. Guys can pair Dunks or Stan Smiths with a monochrome t-shirt and shorts, then finish it off with a colorful windbreaker.
With tailored shorts, a crew neck t-shirt, and low-profile white leather sneakers, you can also go wrong with cool-guy brands like Oliver Cabell, M.Gemi, and Common Projects, as well as high-fashion brands like Prada, McQueen, and Balenciaga.
Loafers are classic mens footwear that looks mature and masculine, making the different styles ideal to wear with shorts in the summer, or create a smart casual to semi-formal look with chino shorts, a button-down shirt, and a blazer for nicer occasions.
For elegant and minimal penny loafers, timeless tassel loafers, and luxurious bit-loafers, go for a classy and streamlined look. Leather bit loafers and dress shorts are a must-have item for any occasion.
High-top sneakers are youthful casual footwear that can work well when worn correctly, from khaki cargo shorts with t-shirts to black chino shorts with sweaters.
Converse, Vans, Nike, and Adidas high-top sneakers are all great options for a casual streetwear look. Pair your Chuck Taylors with denim shorts and a bomber jacket to complete a cool retro outfit.
In the late summer and early fall months, white canvas high-top sneakers may be worn with black shorts, long socks, and a sweater. You may even wear fitted chino shorts, suede high-tops, and a button-down shirt.
Beckett Simonon and Koio offer unique leather-crafted hybrid high-tops that pair well with smart casual outfits, while luxury brands like Gucci and Prada create stylish and daring footwear.
Boat shoes are versatile and easy to wear with shorts, giving you a stylish or casual appearance depending on your outfit. Choose boat shoes that include a refined flair for a weekend power-look or a charming casual touch for an effortlessly chic look.
To achieve a classy ensemble, guys should pair brown leather boat shoes with tailored chino shorts and a dress shirt. Whether you're in New York City or lounging by the beach in Los Angeles, choose a smart casual summer outfit that includes brown leather boat shoes, a white polo shirt, and slim-fit chino shorts.
Boat shoes in neutral hues like dark brown, tan, slate, navy, or beige are always stylish and masculine; invest in bright summer hues to stand out.
Brogue shoes are a great way to pair a classic and timeless look with shorts, while still maintaining a sophisticated silhouette. These dress shoes may also be available in different perforations, such as full or wingtip, half or quarter.
When you want a smart casual look, you can wear linen shorts with an understated lightly-woven shirt and a straw trilby hat. You can wear them with seersucker and top off the look with a luxury crew neck t-shirt or a comfy polo shirt.
Sandals are the most casual footwear that guys wear with shorts for a cool and comfortable look. We recommend buying leather sandals from excellent brands like Birkenstock and Grenson.
Avoid wearing sandals that are too dark, like tobacco and java. Flip-flops can be simple, understated, and matched to your swim shorts or shirt. For an expensive touch, purchase a long-lasting pair of fashion flip-flops, like the Olukai leathers or the Prada brushed sandal.
Espadrilles and shorts are a natural fit for men who want a casual and casual look. They are well-known for being comfortable and great for the summer. espadrilles are classic rope-soled shoes that complement any outfit.
Espadrilles and chino shorts are great ways to look clean-cut and fresh from the boardwalk to a lunch date to a music festival. Wear a linen shirt for a nice classy look, or a button-down shirt for a smart casual look.
For a sophisticated and rugged look, men can always wear shorts with boots. There are many different styles of boot styles and constructions to choose from. Some guys will opt for suede chukka or work boots for a strong masculine look, while others will opt for leather Chelsea or combat boots.
Crepe sole desert boots look distinguished by military or khaki shorts, a hunting vest, and a tan utility jacket. A field watch like the Hamilton Khaki Field or the Rolex Explorer II is a must-have accessory that completes this well-balanced ensemble.
tan Timberlands work boots paired with a t-shirt make excellent streetwear that demonstrates flair and sophisticated taste. You may also opt to pair light suede chukka boots with a navy cardigan or a lightweight shorts.
For a classic wardrobe staple, men can wear dark brown or black suede Chelsea boots. Pair these shoes with shorts and a button-up shirt, or go further with a short-suit.