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For the average style guy, casual shoes are a non-negotiable essential that makes life easier. It’s a pain, literally, to wake up every morning and throw on a pair of dress 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 fall and winter 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 park 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 some of the best sneakers, boots and slip-ons we’re loving right now.
1. Clarks Originals Men’s Desert Boot
THE ALL-SEASON CLASSIC
The Clarks desert boot is an enduring style icon for a reason. And while everyone from J. Crew to Red Wing has their own take on the style, it’s hard to go wrong with the original. Clarks desert boots come in a wide range of autumnal colors, including both suede and leather options. As long as it’s not rainy or snowy, these are boots you can wear pretty much year-round.
2. Converse x Todd Snyder Jack Purcell Low-Top Sneakers
We love everything about these new sneakers, and if you’re a regular reader of SPY, this isn’t the first time you’ve seen them. Part of a recent collaboration between Converse and Todd Snyder, these sneakers are a modern reimagining of the Jack Purcell sneakers, first introduced more than 80 years ago. The new Jack Purcell Low-Top Sneakers are made with an organic canvas upper and a suede tongue and overlay. They also have the classic cap-toe. They’re available in navy blue and cream.
Read More: Most Comfortable Sneakers
3. Frye Austin Inside Zip
BEST WESTERN BOOT
If you want to bring a little yeehaw energy to your fits without looking like you’re running for governor of Texas, Frye is the company for you. Their western-inspired boots work just as well in the badlands as they do on the streets. Cowboy boots are notoriously difficult to put on and take off, but Frye made it much easier with a discreet zipper on the inward-facing part of the shaft.
4. New Balance 327
BEST RETRO SNEAKER
New Balance has a ton of great styles, but the 327 has emerged as a recent standout thanks to its aggressive styling and retro-inspired details. They come in gray with a contrasting green “N” emblem, and the dimpled gum sole evokes classic running shoes. There are several other colors to choose from as well.
5. GH Bass Larson Weejuns
GH Bass’ loafers exist somewhere between a casual shoe and a dress shoe. They’re the kind of shoes you could wear with blue jeans, chinos, or a suit — some people even rock them with shorts. They come in a range of colors, but burgundy is one of the most versatile. Bear in mind, there’s a bit of a break-in period with GH Bass loafers.
Read More: Most Comfortable Men’s Shoes
6. Nike Air Force 1 ‘77
BEST WHITE SNEAKER
Named one of the most legendary white sneakers in a previous SPY article, the Nike Air Force 1 ’77 is a distinctive icon. 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.
7. Clarks Wallabee Boot
The desert boot is the most versatile and classic offering from Clarks, but it’s the Wallabee that has been shining among street style enthusiasts for the past few years. Of course, their popularity is nothing new — the Wallabee is the official unofficial shoe of Ghostface Killah. These boots have been reimagined in an eye-catching pattern that looks like it was cut up from your grandma’s couch, in the best possible way.
8. Converse Chuck Taylor All-Star Hi-Top
BEST CANVAS SNEAKER
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 surprisingly long time if you take care of them properly. The Chuck 70 is the upgraded version of the classic All-Star — it uses a heavier-weight canvas and has a more substantial rubber sole. Plus, it’s a shoe that can be worn year-round.
9. Blundstone Unisex 550 Rugged Lux Boot
BEST OUTDOOR SHOE
Chelsea boots are typically known for being refined, but that doesn’t mean they can’t also be rugged. These sturdy boots from Blundstone, an Australian company known for outdoor-inspired casual boots.
10. Vans Classic Slip-On
BEST SLIP-ON SNEAKER
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.
11. Hunter Men’s Original Refined Chelsea Rain Boots
BEST FOR RAIN
Preparing for wet weather doesn’t have to mean compromising your sense of style. These boots have a sleek, dressy Chelsea boot look, but they’re made from rubber instead of leather. The pull tab at the heel makes it easier to slip these boots on and off. They’re available in black and navy.
12. Greats Court High
BEST HIGH TOP SNEAKER
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 statement, they’re a slam dunk. 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.
13. Common Projects Achilles Neon Suede Low-Top Sneakers
Common Projects is best known for popularizing the white sneaker, a trend that continues to this day. But right now we’re feeling these suede sneakers, available in either neon orange and yellow-green. If you aren’t afraid of spending a little money — and aren’t afraid of bright colors — then this is a men’s casual shoe that’s sure to turn some heads.
14. Allbirds Tree Runners
Allbirds has a dedicated following, and they keep expanding their line of wool running shoes with new options. Allbirds has challenged the conventional wisdom that synthetic materials are best for fitness clothes. These shoes are made with fibers from eucalyptus trees. Just how casual are these casual shoes for men? You can throw them in the wash whenever they get dirty.