The 9 Best Casual Shoes for Men Who Want to Step Out in Style, Comfortably

For the average style guy, casual shoes are a non-negotiable essential that make life easier. It’s a pain, literally, to wake up every morning and throw on a pair of leather monk strap or oxford shoes without developing some sort of blister, cut or worse, a foot injury. Thankfully, men’s style in 2020 has skewed far more casual than ever, bringing the all-day shoe back into the conversation.

The best casual shoes for men should be versatile enough to work with an array of outfits but also comfortable enough to keep up with the demands of whatever you’re doing, like taking a long walk, heading to the beach or simply lounging around. In some cases, your dress shoes could also double as a casual shoe, depending on the outfit.


What Types of Men’s Casual Shoes Are There?


In the realm of men’s casual shoes, there may seem like hundreds of styles exist, but most can be classified into a handful of categories with some overlap.

  • Athletic/Sneakers: A soft shoe with a rubber sole used for sports, walking or performance needs.
  • Boat Shoes: A flat shoe made from canvas and/or leather with a rubber sole that provides traction on wet surfaces.
  • Loafers: A leather or mixed media slip-on shoe that resembles a moccasin, typically with a low block heel.
  • Mules: A shoe with no back or cup around the heel
  • Sandals: An open type of footwear that uses one or multiple straps to contain the foot while leaving it mostly exposed.
  • Slippers: A lightweight shoe, often padded, that is easily slipped on to wear.

For this article’s sake, we’re keeping men’s boots separate because they deserve the respect of detailed examination. As far as men’s casual shoes are concerned, take a look at our top picks.


1. Sperry Authentic Original Boat Shoe


In 1934, Navy veteran and inventor Paul Sperry slipped and fell off the deck of his sailboat. Enraged, he drew inspiration from his cocker spaniel’s paws to create the first slip-resistant deck shoe — a sneaker with pen-knife cuts in the sole which Sperry still produces today. Three years later, he created the original “top-sider,” what we know today as the Authentic Original Boat Shoe with the signature moc toe.

The A/O boat shoe still uses Sperry’s signature vulcanized rubber sole with anti-corroding leather that’s best fit for saltwater use. This shoe is often seen used by recreational boaters and preppy style enthusiasts during warmer months. In some unfortunate cases, they can also be seen “passing” as dress shoes during formal events, which, for the record, is a NO. Instead, wear the Sperry A/O with a cuffed pair of chambray trousers and a loose-fit white linen shirt. It’s a great summertime look that works for all body types.


2. Vionic Charlie Slide Sandal


Sandals are a key element to the summer wardrobe. Although flip flops seem to be the universally popular choice, most are actually terrible options for foot health. Vionic is a brand that specializes in crafting footwear that your arches and tendons will thank you for.

Now, personally, I have never been a sandals kind of guy. However, Vionic’s leather Charlie Slide sandal is a game-changer. The adjustable two-strap design provides better support on the top of your foot. This, combined with the defined arch support, makes walking in these sandals much more comfortable and enjoyable. These sandals look great with a pair of flat-front shorts and a polo shirt. These sandals could also be used interchangeably with the Sperry A/O, depending on your personal preference.


3. On Cloudswift Running Shoe


Born in the Swiss Alps, the brand simply called On sought to revolutionize the sensation of running by emulating their interpretation of running on clouds. Today, these running shoes have exploded into the mainstream retail market with their innovative designs. On’s Cloudswift running shoe was designed specifically to handle the variances and harshness of urban terrain to provide the runner with an explosive toe-off after each heel strike. The pull-on sock design and lace cage provide excellent support in addition to the removable neutral stability insole. Wear these insanely comfortable shoes on your daily run, rain or shine, to get the most out of your footwear.


4. Nike Air Force 1 ‘77


Voted one of the most legendary white sneakers in a previous SPY article, the Nike Air Force 1 ’77 is well known to most people in the modern world. One of Nike’s most iconic sneakers, the Air Force 1 is a basketball-turned-fashion sneaker that helped shape the global sneaker culture as we know it. The white-on-white colorway may be the most popular version of this sneaker, given its crispy, clean look and versatility to match with anything from denim to track pants and, on some occasions, camo shorts. This is one of the best casual shoes for men, but do yourself a favor and also pick up a Jason Markk kit when you cop these. Stay cool and casual and rock these with a pair of athletic shorts and a t-shirt or be bold and rock it with a full suit, both look fantastic.


5. Cole Haan Nantucket Loafer


Cole Haan is arguably one of THE best makers of sneaker sole dress shoes, and the Nantucket Loafer is no exception. A canvas upper, rubber sole and leather penny keeper strap make up a versatile moc toe loafer that’s perfect for warmer weather. This is one of the brand’s innovative designs, like the ZeroGrand collection, which meshes the silhouette of a dress shoe with the cushion and casual style of a sneaker. This shoe is the perfect foundation for smart-casual style with endless outfit options.

Think about wearing these incredibly comfortable shoes with a light wash or shite pair of skinny jeans and one of those horizontally striped t-shirts in a natural tone with blue stripes. If it’s a windy day, toss a lightweight chambray button-up shirt over and call it done.


6. Vans Classic Slip-On


Some may know this as the Spicoli shoe from Fast Times at Ridgemont High. Some may know it as that shoe all the hardcore kids wore back in ‘04. Others know it as their favorite slip-on shoe that’s tattered and dirty and still awesome. Vans’ Classic Slip-On, especially the black and white checkered, is nothing short of iconic, building its fanbase in the late ‘70s skateboard scene which was largely dominated by the Vans brand. Today, the slip-on shoe is worn both as a skateboard shoe and a casual shoe, complementing laid-back, effortless style.

This slip-on shoe is made with a canvas upper and padded collar and footbed for all-day comfort. The vulcanized rubber waffle sole is Vans-standard and provides excellent flexibility for skating or walking. This is one of the best casual shoes for men who like to show off some ankle. Try wearing these with a breezy pair of joggers, and one of the many fun Vans graphic tees.


7. Greats Court High


The Greats Court High in Nero is one of the best casual shoes for men who live life in dark jeans. The “court” refers to the style’s basketball inspiration. And while we don’t recommend using these when shooting hoops, as a fashion and ecological statement, they’re a home run. These made-in-Portugal high top sneakers are mixed media, with a suede and leather upper and fully recycled rubber sole. Greats made sure this shoe is 100% biodegradable and that manufacturing is done with the highest level of environmental and labor practices. Wear these with your favorite dark skinny jeans and a clean black top, graphics optional.


8. Soludos Road Trippin’ Espadrille


Finding a good pair of casual men’s shoes for the beach can be difficult. Most times these shoes look more like equipment rather than stylish footwear, but Soludos may be the best Solu-tion for this issue. The Soludos brand is well known for its quirky espadrille shoes, like this one, with fun prints or graphics. Espadrilles are essentially a woven rope-soled shoe, most times with a canvas upper and rubberized sole, which makes them easy to clean if they get wet or sandy. Wear these with your typical beachwear or, if just wearing for style, sport these with a linen pant and a printed camp collar shirt.


9. Trask Seth Loafer


Sometimes the best casual shoes for men come in the form of a dress shoe, but it depends on the outfit. This loafer from Trask is a perfect example of how to accomplish that. The Seth loafer is a weathered-looking leather loafer with white stitching and a rope accent that sits on a block heel. To make this loafer work as a casual shoe, add it to a pair of jeans and a navy blue t-shirt to make it look cool, clean and casual. Or, rock it with some drawstring shorts and a striped t-shirt to have even more casual fun.


We Asked Menswear Influencers to Pick the Most Stylish Men’s Shoes for Spring 2020