These Are the Most Comfortable Loafers on the Market (2024)

Leave it to Madewell to give us the perfect wear-everywhere shoe. The brand mashed up the classic loafer silhouette with a not-too-chunky lug sole, and the result is a chic pair that feels more timeless than trendy. “I love how they have the chunky vibe but still look sleek (and don’t weigh, like, 10 pounds),” says Glamour contributor Lindy Segal. “I’ve been wearing them solo with straight-leg jeans this fall, but I plan to layer them over knit tights and socks through winter so I can pair them with dresses and skirts.” We also love that there’s a puffy strap instead of a more traditional penny band.

Sizes: 5–12 / Colors: 3 options / Material: Leather

Pros: Grippy outsole; relatively lightweight; half sizes available
Cons: Sizing might run large

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Seeking out slim, supportive loafers to be your summertime walking shoes? Your search ends here. This velvet pair contains Vionic’s podiatrist-approved insoles (which offer plenty of arch support, by the way) to cradle your feet as you walk. Wear them with a suit during the week, then a cashmere sweater and jeans on your weekend getaway.

Sizes: 5–11 / Colors: 3 options / Material: Leather or suede

Pros: Podiatrist-approved design; supportive insoles; half sizes and wide width available
Cons: Limited colors

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Name a more timeless penny loafer—we’ll wait. This time-honored preppy shoe looks just as cool with tailored suits as it does with cargo pants or running shorts, and we can’t resist styling them with white crew socks for extra geeky-cute points. “My pair was comfortable right out of the box—no blisters,” Glamour commerce writer Jake Smith says. “The sizing runs a touch large, so if you’re unsure, consider going down by a half size; the leather will stretch to accommodate your feet.”

Sizes: 5–11 / Colors: 5 options / Material: Leather

Pros: Classic silhouette; durable leather; half sizes available
Cons: Might run large

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Pretty much the definition of the classic penny loafer, these J.Crew shoes are longtime bestsellers. To be frank, this is the one loafer style you really should have in your rotation. If brown and black patent leather are too plain, you can also pick up a two-tone linen style or a more intricate Italian woven leather. “What captured my heart is the beautiful woven leather and the striking contrast it offers,” says Glamour commerce producer Leilani McQuay. “Not only do they give a clean and chic look, but they also offer a snug fit that wraps your feet in pure comfort. I’ve been experimenting with different outfit combinations, from jeans and a classic button-down to pairing them with socks and a miniskirt.”

Sizes: 5–12 / Colors: 5 options / Material: Leather

Pros: Traditional silhouette; durable sole; half sizes available
Cons: Might run small; require breaking in

Bookmark these for when the “What loafers should I get?” texts from friends start rolling in. Everlane designed these minimalist beauties with all the classic features: supersoft leather, a delicately tapered toe, and a one-inch stacked heel, plus a cushioned insole that cuts down on break-in time.

Sizes: 5–11 / Colors: 2 options / Material: Leather

Pros: Simple design; comfortable feel; half sizes available
Cons: Might be too narrow

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These multicolor loafers are a hit among celebrities like Nicole Kidman and the Hadids Bella and Gigi. It’s no wonder; they’re padded with memory foam for extra comfort and feature a gold buckle in the shape of a hand for extra oomph. “The craftsmanship is impeccable. People will inevitably ask where you bought your pair—and if you’re nice, you’ll tell them,” says commerce writer Jake Smith.

Sizes: 35.5–42 EU / Colors: 1 option / Material: Leather

Pros: Unique design; slight heel; half sizes available
Cons: Pricey

Adding a lug sole and horsebit hardware to its more classic loafers, G.H. Bass created perhaps the preppiest shoes on the market. (Just imagine these with a tweed suit.) “These feel like you’re walking on a literal cloud” says Glamour commerce director Brie Schwartz. “I can wear these for hours and they’re as comfortable as my go-to sneakers, because they’re light as air. I also love how the extra height gives them a little bit of edge.”

Sizes: 5–11 EU / Colors: 2 options / Material: Leather

Pros: Lug sole; comfortable design; half sizes available
Cons: Break-in time required

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Steve Madden took a classic black leather upper and remixed it with metal penny hardware and a chunky rubber sole. The block heel gives it a welcome (but still walkable) height boost that’s just as appropriate for the office as it is for a night out. “Measuring in at a whopping five feet, zero inches, I am always in search of a bit more height, so any shoe that has a chunky sole piques my interest,” says Glamour junior designer Channing Smith. “These Steve Madden loafers are extremely walkable and sophisticated without feeling aggressively preppy. Truly a staple in my wardrobe, they pair easily with a trouser for a chic work look or a miniskirt and silky socks on the weekends.”

Sizes: 5–11 / Colors: 4 options / Material: Leather

Pros: Comfortable design; height-boosting sole
Cons: Might be too narrow

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These lug sole loafers score major points in the versatility department: Try them with thicker ankle socks and a slip dress to keep the grungy vibes going, or elevate a graphic tee and pair of high-waist jeans by styling them with sheer or patterned socks. “In the last few months, I’ve worn these at least once a week—to work and casual outings, because they are perfect for almost every occasion,” says Glamour editorial assistant Monique Wilson. “I love the platform detail and the brown and black color-blocking. I definitely want to get the same pair in other colors.”

Sizes: 5–11 / Colors: 5 options / Material: Faux leather

Pros: Lightweight design; height-boosting soles; half sizes available
Cons: Not real leather

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Made from soft black leather and pulled straight from your ’90s fantasies, these chunky loafers are perfect do-everything shoes. “I’m always impressed by the soft leather and the serious soles,” commerce writer Smith shares. “After a short break-in period, these slip-ons are supremely comfy and seemingly indestructible. They’re a touch heavy and the sizing does run a little large, so go down if you’re between sizes.”

Sizes: 6–11 / Colors: 1 option / Material: Leather

Pros: Durable design; grippy outsole
Cons: Might run large; limited colors

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These iconic kicks need no introduction. There are many designer loafers to choose from—Bottega Veneta, Tod’s, Louboutin—but we’re partial to Gucci’s laidback, extra-comfy pair featuring the brand’s signature horsebit hardware and foldable back. There have been many iterations through the years, each just as stylish as the last. “Though the leather is buttery soft, these loafers have withstood long walks on gritty NYC streets,” commerce director Schwartz says. “The most comfortable shoes I’ve ever owned, they have no painful break-in time, nor do they cause blisters, and I love the iconic OG horsebit detail. Plus, they can also be worn as slides.”

Sizes: 4–12 / Colors: 2 options / Material: Leather

Pros: High-end materials; iconic design; versatile silhouette; half sizes available
Cons: Pricey

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Can’t get enough color in your wardrobe? Keep Free People’s vibrant penny loafers on your radar. While all the neutrals are available, the standouts are the more unusual options, including apple green, blush pink, vibrant coral, and rich olive. Better yet, each pair features a sturdy lug sole and a metal “coin” in the penny slot, adding even more personality to your footwear.

Sizes: 6–11 / Colors: 8 options / Material: Leather

Pros: Eye-catching colors; metal detail; durable soles; half sizes available
Cons: Can take a while to break in

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Leather loafers are a notoriously bad choice for rainy days—but Tory Burch’s slip-on shoes provide a delightful workaround. They reimagine the classic style in waterproof rubber in three distinct colors: yellow for the bold, black for the traditional, and ivory for the white sneaker enthusiasts. Reviewers rave that they’re comfy, too, thanks to a jersey footbed that provides plenty of cushioning. Plus, the branding is minimal, with a small logo at the vamp.

Sizes: 5–11 / Colors: 3 options / Material: Rubber

Pros: Lightweight design; height-boosting soles
Cons: Not real leather

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Mary Jane shoes are everywhere right now, whether you’re a fan of the loafer or the ballet flat. Reformation’s take is an appropriately cool revamp of your girlhood shoes, now outfitted with chunky soles and an inclusive size range. No matter what you wear—we suggest wide-leg jeans and some minimal jewelry—opt for these slip-on loafers and you’ll look like a fashion editor.

Sizes: 5–11 / Colors: 1 option / Material: Leather

Pros: Trendy look; adjustable straps; half sizes available
Cons: Only available in black

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Sometimes, buying a random pair of loafers off of Amazon works out. That’s exactly what Glamour commerce writer Andrea Navarro learned when she picked up this tasseled gem for a last-minute Gossip Girl costume. “I was shocked at how comfortable they are, and while I wasn’t planning on wearing them often, I’ve found myself slipping into them weekly,” she says. “I’m not mad about it since the price tag is on the more affordable side.”

Sizes: 5.5–9.5 / Colors: 1 option / Material: PVC

Pros: Affordable; comfortable insoles; half sizes available
Cons: Limited sizes available; not real leather

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Coach’s ultra-preppy drivers feature soft, stretchy leather and outsoles that don’t slip, meaning they’re great for anyone who’s frequently on their feet. And since these driving moccasins are made of such a soft material, they require little break-in time—see you never, blisters.

Sizes: 5–11 / Colors: 8 options / Material: Leather

Pros: Comfortable design; grippy outsoles; half sizes available
Cons: Might run narrow