6 Men's Shoes to Wear with Shorts this Summer

The sunshine and warm weather of summer likely have you trading your jeans and long pants in for shorts. But, when switching up your wardrobe for the season, you shouldn’t leave your shoe collection trailing behind. 

Wearing men’s summer shoes with shorts is a fantastic way to align your easy-breezy summertime mood with your seasonal wardrobe. That’s why we’ve crafted a guide that explores the six best men’s shoes to wear with shorts.

#1 Sneakers 

Every man needs a pair of comfortable sneakers, whether you’re opting for outdoor outing or spending your afternoon sipping brews on rooftop patios. Fortunately, you can match a sneaker with almost every pair of shorts in your wardrobe. 

Whatever look you're going for, sneakers can help you get there. Among the best men’s shoes to wear with shorts are sneakers, which offer a sporty way to personalize any summer outfit. Use your favorite sneakers for men to:

  • Make a casual statement – Pairing sneakers with athletic shorts and a t-shirt says you’re ready to relax, making it the perfect look for casual get-togethers like backyard BBQs or pick-up games in the park.
  • Enliven dressier looks – You can wear sneakers with chino shorts and a button-down for a look that’s appropriate for casual affairs. If you really need to up the ante, you can add a blazer.

Opt for a white sneaker like the TOMS Fenix, paired with either denim shorts or chinos for a cool, casual shoe look that suits any guy.

#2 Boat Shoes

Among the best men’s shoes to wear with shorts are boat shoes. Originally intended for seafaring—or at least for lounging on expensive yachts—the classic boat shoe toes the line between upper-crust formality and casual summer style. 

Pairing boat shoes with a pair of Bermuda shorts and a polo shirt or printed shirt puts an intellectual spin on a classic casual look. On the other hand, you can dress them up with formal shorts and a tailored shirt and blazer. 

Although boat shoes come in about as many colors as you can think of, you’ll get more wear out of them if you stick to neutral colors like:

  • Brown or tan
  • Navy blue
  • Beige

Be sure to wear your boat shoes with invisible socks or no socks at all for that classic maritime look. The TOMS Claremont Boat Shoe is a hybrid shoe between our iconic Alpargatas and the beloved boat shoe. The shoe is complete with functional laces and TOMS CloudBound™ Sole, which provides increased comfort and better traction to get you through any slippery situation.

#3 Loafers

If you need a shoe that can be worn to casual events or dressier occasions, invest in a pair of loafers. A staple of men’s fashion for decades, loafers look great with almost any kind of shorts, from Bermudas to denim shorts to chinos. 

Loafers come in about eight distinct styles. The most popular include:

  • Penny loafers
  • Tassel loafers
  • Horsebit loafers

#4 Espadrilles 

If you don’t already own a pair of espadrilles, now is the time to change that. When it comes to wearing men’s shoes with shorts, espadrilles are a must-have.

This is because espadrilles are among the most versatile summer shoes you can buy. Whether you’re wearing chino shorts to a casual lunch or wearing your swimming trunks on the boardwalk, espadrilles are the right choice.

#5 Sandals 

Of all the types of men’s shoes, one of the best men’s shoes to wear with shorts is also one of the best summer shoes for men, period. From flip-flops to sliders to gladiator sandals and every style in between, sandals are the classic shorts pairing.

Depending on the sandal style and the shorts you wear them with, you can make this type of footwear appropriate for a variety of occasions. While they’re an obvious partner to your swim shorts for a day at the beach, you can also pair them with nicer shorts like chinos for a chic summer soiree. 

#6 Borgues 

If you want to make a classic, refined statement that still matches the warm weather, brogues are the shoe you should choose. As classic men’s dress shoes, brogues are the perfect way to dress up for summer.

Brogues are characterized by their fine leather uppers, decorative perforations, and wingtips. And they come in three distinct styles:

  • Full brogue
  • Half brogue
  • Quarter brogue 

Pairing brogues with chino shorts and a tailored Oxford shirt creates a look that’s casual without being slouchy. And adding a smart jacket or even a tie can elevate the look for those slightly fancier evening events. 

TOMS: The First Name in Summer Shoes 

There are a lot of shoes that complement summertime shorts. But none look quite as good as a pair of TOMS.

No matter what kind of shorts you’re wearing—or where you’re going in them—TOMS has the shoe that’s right for you. From our classic espadrille styles to summertime staples like boat shoes, slip-ons, and casual sneakers, you’ll be ready for whatever the season brings you in a pair of TOMS.

Plus, every pair of TOMS is made sustainably and features design perks to maximize style, comfort, and wearability, like padded collars, textured uppers, and our OrthoLite® Eco LT Hybrid insoles. 

It’s time to put a little summer in your step. And with over 150 styles for under $30, there’s no reason to wait. Shop now. 


Reviewed By Andrew David Stewart

Andrew David Stewart is the Manager of Digital Marketing at TOMS and has been working in the digital marketing and social media world for 6 years. Andrew is a lover of nature and the outdoors, and is passionate about telling stories through digital media.