From ’80s preps to Succession (Kendall favors Loro Pianas), the loafer has always been a consistently cool shoe and perhaps the most versatile item in your wardrobe. “Loafers are the epitome of effortless transitional footwear,” says Kevin Kafesu, a former buyer at Norse Store in Copenhagen. Kafesu says that if you choose well, loafers are the most comfortable shoes you can own. “Generally, the structure of most options — soft leather, sturdy bottom, slip-on design — tend to be crafted with comfort in mind, keeping you right on your feet for long-hour days.” Jian DeLeon, men’s fashion director at Nordstrom, loves how a loafer spans subcultures to fit a range of styles — punk right down to Americana. “The loafer has been a mainstay on the feet of cool kids for a while; it certainly isn’t going anywhere,” he says. “It hits that sweet spot of ‘classic with a twist’ that makes modern menswear staples so exciting.”
Another benefit of loafers, says Jeremy Kirkland, the creator and host of the menswear podcast Blamo!, is that they slowly shift and mold to your feet. Once you break them in, the fit can feel perfect. His biggest suggestion is to pick a pair that begin in a shape that’s close to that of your foot. “Different companies have adjusted their lasts (the mold a shoe is made on) over the years to accommodate a wide range of feet,” he explains. So when you find one you like, stick with it.
We spoke to DeLeon, Kafesu, Kirkland, and nine other stylish men to discover the best loafers at every price point. Here are their picks, including the best penny loafers, tassel loafers, and horse-bit loafers.
Best loafers under $200
The Dr. Martens Adrian loafer comes recommended by three of our style experts. “First and foremost, they just look the business,” says Paul Toner, online editor of 10 Magazine. For Toner, they’re as wearable for a friend’s wedding as they are for a chill day out. “There’s a classicism to them that makes them ideal to both dress up and dress down.” DeLeon agrees and also loves their versatility in fitting different styles. Both Toner and Kafesu say their Dr. Martens are surprisingly durable. Toner is still wearing a pair he bought six years ago. Meanwhile, Kafesu wears a pair from 2018 “on a weekly basis.” Kafesu says it’s down to the expertly crafted leather structure — a black polished smooth type, with the upper and sole both heat-sealed and sewn together — that makes them top of the range despite the lower price point (the shoes are designed in London’s Camden but made in various countries across Asia). “The Adrians are a classic, and their comfort is unmatched thanks to the bouncy soles,” says Kafesu. “But beware, that leather is so good it takes a while to break in. Remember to pack Band-Aids for those first few wears unless you want to walk around like a penguin.”
Strategist columnist Chris Black is a fan of the classic Bass Weejuns. “This is some real Take Ivy shit, but I am here for it,” he says. “These have moc stitching, which I love, and the price is right. Affordable stunting: You love to see it.”
“I’ve been wearing loafers for as long as I can remember,” says Strategist contributor Chadner Navarro. “I own over two dozen pairs, and the ones I’ve been living in for nearly a year are Wolf & Shepherd’s Monaco loafers in cognac.” Navarro says the unlined soft Italian suede is perfect for traveling. “You really can flatten them down without feeling like you’re going to destroy them. I enjoy how the shape is narrower, giving it a slightly dressier silhouette without being witchy-pointy.” Plus, the back part of the shoe that covers your heels folds down, so you can rock them as mules.
Best loafers under $400
Blackstock & Weber was recommended by multiple stylish men we consulted, including former Strategist associate editor Louis Cheslaw. “When I want to wear a pair of loafers more casually, I’m wearing my Blackstock & Webers,” he says. “While my other dress shoes only really work with more formal outfits, B&W’s chunkier, more modern, almost sneakerlike shape slots in easily with wide jeans, shorts, and gym socks as well as suits.” Jordan Bunker, a menswear writer and blogger, says, “You can easily see how a pair of Blackstock & Webers could be worn 24/7. You don’t call yourself ‘The Best F- - - - - - Loafers in the World’ without being multifunctional.” These loafers took design elements, like a more rounded toe and chunkier sole, from classic sneakers. They also use pebble-grain leathers, vibrant colors, and premium suedes that turn loafers into a shoe for a more modern era of dressing. “It’s putting a playful spin to loafers,” says Kafesu. “And thankfully, the company still acts like a classic shoemaker. The designs are timeless, the materials are the highest quality, and there are experts on hand to help with any questions you might have before purchasing,” adds Cheslaw.
If you’d like to spend a little extra, Dr. Martens has a Made in England range, where the shoes are made in the company’s original factory in Northampton.
These are the only penny loafers Nicolas Lazaro, editorial manager at Buck Mason, will wear; in fact he owns three pairs. “Asking to pick a favorite among them is like asking to pick a favorite child,” he says. His Black Calfs are the ones he wears the most, though he likes to pair his Brown Grain loafers with tweeds and denim as a good fall and winter option. “I like the plays on texture here; there’s pebble grain down to suede, and a refinement usually associated with brands at a higher price point,” he adds. He has had to pay slightly more for them this past year but still thinks the price is worth it: “I think it’s a testament to the quality that I’m still wearing mine nearly every day. They don’t skimp or do any other corner-cutting to reduce costs.”
London brand Percival is usually known for its sleek, tailored menswear rather than shoes, but Lazer, the founder of Nobo Agency, flags its collaboration with shoe brand Duke + Dexter as his favorite. “It’s luxury craftsmanship at an amazing price point,” he says. The penny loafers are made from a mix of Italian suede and leather and a compounded rubber sole that means they’re built to last. There are two designs in the collection, both inspired by an English garden. Lazer especially likes the detailing, adding that “they complement various outfits; they’re perfect for any event.”
Best loafers worth splurging on
Church’s is a heritage brand dating back to the 1800s, known for shoes made by hand in Northampton, England. For Bunker, its Pembrey loafers are some of the most reliable in his wardrobe. He’s been wearing his pair for years, and they’re the ones he’s “banked many steps in. I think if you’d have asked for an answer in three, five, or even ten years’ time, my love for the Pembrey would still be there,” he says. Virgil Nicholas, the creator of the footwear brand Vinny’s, also recommends the Pembrey. He says it has a heavy-duty construction; the shoes are Goodyear welted, which means the outsole, insole, and upper are stitched together with a strip of leather, and you get a sense of the craftsmanship once it’s on your feet (the brand favors calf leather, which easily molds to your feet). Timothy Grindle, co-owner, manager and buyer at Boulder-based clothing company Canoe Club, is a fan too: “The silhouette is just right — not too low and not too chunky,” he says. “They feel luxurious but also like I can run them into the ground.” And if you are hard-wearing with your shoes, note that the brand offers an in-house repair service to get them back into shape.
Based in France, Paraboot is best known for its sturdy goat-leather moc-toe Michael shoe. But Kafesu says an investment in its cleated-sole Reims loafer will definitely pay off. “What I love about them is the unbeatable combination of durability and affordability considering they’re handmade in France,” he says. “These shoes are built like a tank. If you need any proof of their longevity, I noticed a brand owner wearing a 25-year-old pair in their Milan showroom some years back.”
This is the loafer Kirkland has had the longest (for over six years). “It’s like the classic penny loafer. It has a wider last and can accommodate almost any foot,” he says. The flattering shape will appeal to people who are fans of the classic Ivy or trad style.
Four of our experts recommended Gucci’s Horsebit loafers. They’re the longtime favorite of Grindle’s. “If you hit me back in 2 years or 30 years, I can’t imagine answering differently. We have had no shortage of loafers come through the shop, but the Gucci loafer is the icon. It is clean, elegant, easy to dress up or down — it’s the perfect loafer.” Kafesu and DeLeon are also fans. DeLeon suggests opting for some of the newer statement colors of the shoe now on the market, like a dark forest green.
DeLeon points out that while it is JM Weston’s 180 loafer that usually gets the most hype, the brand’s more casual Le Moc has become one of his recent favorites. “Not just because it’s slightly less expensive but because they come in more fun colors like an on-trend ice blue. Plus the suede uppers are comfortable from the first wear.”
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