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The 11 Best Loafers for Men to Buy in Winter 2021

These days, we’re all probably living in our fuzzy slippers since we’ve been working from home (no judgment), especially as temps continue to be frigid across much of the country. But, if you’re in the mood to dress up, might we suggest slipping on some loafers. A shoe made for the guy on the go or the guy at home, these low, laceless slip-ons look great with just about anything. Made to be worn with selvedge denim, white T-Shirts, Oxford shirts, and more, they’re about as classic as it gets.

We mean that literally — loafers have a rich history that dates back almost a century, with roots in 20th-century Ivy League style. Even though today, these slip-ons are synonymous with bourgeois leisure (and Wall Street bankers), they were originally worn by fishermen in Norway, and the easy-to-wear silhouette made its way through Europe, and eventually to America in the 1930s.

Today’s loafers are modern, fresh, and timeless. With that spirit in mind, we put together a guide to the best loafers, broken down by category. Shop away to your heart’s content.

Best Loafers Overall: G.H. Bass Larson Weejuns

G.H. Bass Larson Weejuns

In 1936, G.H. Bass was the first American brand to create a local interpretation of the slip-on, Bass Weejuns, a pun off, you guessed it, “Norwegian.” They are also referred to as the original penny loafer, because legend has it, students would tuck a one cent coin in the front slot of their shoes to use for pay phones. Almost a century later, these loafers are still G.H. Bass’ bestsellers and can be worn in retro or modern style. Pair them with rugged jeans and a gray tee for a dash of devil-may-care attitude, or team them up with a khaki chino suit. To us, those sound like the best loafers overall … period.

Best Luxury Loafers: Gucci Leather Bit Loafers

Gucci Leather Bit Loafers

These instantly recognizable leather bit loafers have become a status symbol among investment bankers (and have inspired a legion of knockoffs), but they look just as polished outside of Wall Street. Made to be worn with your sharpest suit, or your simple shirt-and-jeans combo, these Gucci loafers can instantly elevate any fit for generations to come, and they’ll live up to your investment.

Best Statement Loafers: Artemis Design Co. Sumak Kilim Loafers

Artemis Co loafers

Artemis Design Co., an Istanbul-based footwear upstart, has rightfully gained a cult following for their intricately designed, head-turning shoes. Case in point: these gorgeous loafers sourced from Turkish carpets, and embroidered with red, white, and blue prints of animal iconography.

Best Leather Loafers: Allen Edmonds Lake Forest Penny Loafers

Allen Edmonds Lake Forest Penny Loafers

Ready to invest in the best leather loafers? Of course you are — that’s why we’re here. Allen Edmonds takes the same meticulous approach to these sleek black loafers as it does with its durable dress shoes and boots. This means you can wear these handcrafted leather loafers with everything from a navy cotton suit to slim black denim and a white Oxford shirt (think Alex Turner a la the Arctic Monkeys).

Most Comfortable Loafers: Sperry Plushwave Penny Loafers

In general, our favorite loafers are much more comfortable than other dress shoes, but if you want an especially cozy slip-on to wear while working from home, you can’t go wrong with these Sperry Plushwave Loafers, which blend the iconic penny loafer silhouette with a well-cushioned, springy sole. Because these toe the line (pun intended) between dressy and casual, we recommend wearing them as part of a high-low combo of slim olive chinos, a white Oxford shirt, and a navy blazer. Looking for that extra comfort? You might want to consider wearing no-show socks under.

Best Value Loafers: Urge Marakesh  Shoes 

You don’t have to spend a pretty penny to cop quality loafers. Swing through Bespoke Post to pick these breezy slip-ons, which feature hand-stitched side detailing that style for those cold winter days. Pair these up with linen trousers and a slub polo for laidback weekend style — just add, say, an Old Fashioned or a martini.

Other Loafers We Love

Nisolo Alejandro Slip-Ons

Nisolo Alejandro Slip-Ons

Nisolo makes its stylish loafers ethically at one of the world’s best shoe factories, and it helps that these fashionable slip-on shoes feature a laidback silhouette and a design that’s just different enough to separate them from the pack.

Crockett and Jones Boston Loafers

Crockett and Jones Boston Loafers

Step right into a handsome pair of loafers made by this James Bond-approved British heritage footwear maker. While Bond needs something a little more functional than loafers, these sharp brown suede loafers are perfect for us mere mortals. Wear them with white jeans and a navy polo, accessorized with classic Aviator sunglasses.

Florsheim Berkley Moc Toe Penny Loafers

Florsheim Berkley Moc Toe Penny Loafers

We’re totally in favor of classic loafers that are a bit bold at the same time — take the eye-catching Burgundy colorway found on these Florsheim penny loafers, and at a great price, to boot.

Yuketen Suede Penny Loafers

Yuketen Suede Penny Loafers

We’ll close things out by looking at some of the best suede loafers yet again. Yuketen makes the best men’s shoes and boots with a stunning level of craftsmanship, quality, and value, reflected in the price tag. And yet, you’ll have these loafers for years. Wear them at your cabin with olive camp pants and a white pocket tee while keeping warm during winter mornings (coffee is required, of course).

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