Step Out in Style: Our 15 Favorite Casual Men’s Shoes for Summer 2021

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 2021 has skewed far more casual than ever, bringing the all-day shoe back into the conversation. For Summer 2021, the best men’s casual shoes are equal parts comfortable, laid back and stylish.

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.

Finally, while there are plenty of designer sneakers, if you’re paying $500 or more for your shoes, how casual are they, really? Below, we’ve shared the 15 sneakers, boat shoes and sandals we love the most right now.
   Our Favorite Types of Casual Shoes for Men
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. Of course, sneakers aren’t just worn for performance, and there’s an entire sneakerhead culture devoted to collecting stylish and rare sneakers like Air Jordans. Boat Shoes: A flat shoe made from canvas and/or leather with a rubber sole that provides traction on wet surfaces. Click here to see our favorite boat shoes of summer 2021. 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 below.
   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.
Buy: Sperry Authentic Original Boat Shoe $94.95    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.
Buy: Vionic Charlie Slide Sandal $119.95    3. Converse Chuck 70 Expressionist Icon High-Top Sneakers
You can’t talk about the best men’s casual shoes without talking Converse, and you’ll find the sneaker brand well represented on our guide to the best men’s casual shoes for Summer 2021. Our top pick? These high-top paint splatter sneakers, which are sure to earn you plenty of compliments. These sneakers are available in both black and white, and you can’t go wrong with either option. Last year, the Converse tie-dye Chucks were the shoes of summer, and we expect these new colorful Chucks will be in high demand this year.

Buy: Converse Chuck 70 Expressionist Sneakers (Black) $90.00

Buy: Converse Chuck 70 Expressionist Sneakers (White) $90.00    4. 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.
Buy: On Cloudswift Running Shoe $149.95    5. Nike Air Force 1 ‘77

Named 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.
Buy: Nike Air Force 1 77 $90.00    6. Converse Chuck 70 in Wolf Grey

While you can’t go wrong with classic black or white Chucks (or the always-trendy Comme des Garçons Play x Converse Chucks), we recommend adding a dash of color into your summer style with these Chuck 70 sneakers in the Wolf Grey colorway. These sneakers are available in both low- and high-top, so pick the style of Chucks that suits you best. These canvas sneakers never go out of style, so re-up for summer with some of the best casual men’s shoes of all time.
Buy: Converse Chuck 70 in Wolf Grey (Low Top) $80.00 Buy: Converse Chuck 70 in Wolf Grey (High Top) $85.00    7. Wolf & Shepard Ringer Loafer

A classic-style loafer is one of the best shoe silhouettes in the market, capable of pairing alongside a ton of different looks — causal or otherwise. And if you recently traded in your skinny jeans for boot cut or straight leg, then you’ll need some new shoes to go with them. While dressy casual shoes might seem like an oxymoron, loafers and slip-ons are perfect for casual summer outfits. Case in point: the Ringer Loafers from Wolf & Shepard.

Wolf & Shepard is a relatively new player in the dress shoe space, but their Ringer Loafer has made an incredible splash. The premium Italian leather will age extremely gracefully and will look good with every single outfit you put together. The real feature on these, however, is the extremely comfortable insole; made from the brand’s proprietary FloatFoam, the footbed does really feel like you’re walking on plush foam with every single step, making it just as comfortable as your favorite sneaker. 

Buy: Wolf & Shepard Ringer Loafer $175.00

   8. 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 your 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.
Buy: Vans Classic Slip On $49.95    9. 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.
Buy: Greats Court High $209.99    10. Mulo Suede Espadrille

While Mr. Porter actually lists these Mulo Espadrilles as loafers, don’t get it confused, they’re most certainly espadrilles. This beach classic gets a bit of an upgrade thanks to a buttery brown suede upper and contrasting rubber soles that are great for walking on both the hot sand and the hot pavement. Pull tabs on the back of the espadrilles make them easy to take on and off when you’re really ready to hit the beach and get out in the sun while the cushioned support will keep your feet relaxed as the day stretches on and on.

Buy: Mulo Suede Espadrille $225.00

   11. 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.
Buy: Trask Seth Loafer $210.00    12. Keen x Engineered Garments UNEEK Leather Slide

A good slide is an essential staple in every summer wardrobe, making it easy for your feet to get some air and breeze on brutally hot days. But sometimes you need something that’s a step above what you’d typically wear to the pool, which is where these leather slides from Keen and Engineered Garments come into play. They’re supported by Keen’s excellently cushioned sole and given a stylish upgrade thanks to Engineered Garments’ penchant for great leather details. It’s a bold shoe for a bold dresser and one that’s bound to turn heads.

Buy: Keen x Engineered Garments UNEEK Leather Slide $160.00

   13. Converse Chuck Taylor All-Star Hi Top

You can’t go wrong with a timeless canvas sneaker, and the best to ever do it is the Converse Chuck Taylor. Chucks can be dressed up or down depending on the mood of your outfit and can last a really long time if you take care of them properly, making a shoe that’s great to pair with shorts or even a suit if you style it correctly. The only limit is your imagination and creativity. Plus, the canvas is a little more breathable than other shoe materials like leather, so it’s a great year-round shoe.

Buy: Converse Chuck Taylor All Star Hi Tops $84.95

   14. Chamula Rio Grande Huaraches
If you’re looking to get in on the ground floor of a new menswear trend, consider the huarache. The breezy sandal is crafted by artisans in Mexico using vegetable-tanned leather that will eventually conform to the shape of your foot to ensure a premium level of comfort. These from Chamula are exclusive to Huckberry and feature a durable, flexible, and comfortable EVA sole.

Buy: Chamula Rio Grande Huaraches $130.00

   15. Adidas NMD Sneakers
We love Adidas sneakers here at Spy, and if you need a pair of comfy and stylish everyday sneakers to wear with your favorite joggers or athletic shorts, then you can’t do better than the Adidas NMD line of trainers. While the NMD line is available in a wide range of colorways, if you’re looking for the best casual men’s shoes for Summer 2021, then we’d recommend sticking with either the black or white colorways, both linked below.

Buy: Adidas NMD Sneakers (Black) $140.00

Buy: Adidas NMD_R1 in White $140.00

The Best Men's Boots of 2021
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