Fall’s Secret Weapon: Why Loafers Are This Season’s Power Move

From heritage penny loafers to Italian designer picks, these 20 pairs of loafers prove boots aren’t the only answer to autumn style.

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LONDON, ENGLAND - JUNE 09: David Gandy wears a blazer jacket, a white t-shirt, sunglasses, during London Fashion Week Men's June 2019 on June 09, 2019 in London, England. (Photo by Edward Berthelot/Getty Images)

Let's dispel a persistent myth: loafers aren't just summer shoes. The notion that these versatile slip-ons should be relegated to warm weather is perhaps one of men's style's most unfortunate misconceptions. While every other gentleman is predictably rotating through their Chelsea boots this fall, the smartest dressers know loafers are having a moment—and for good reason.

First, consider the practicality. Modern loafers pair exceptionally well with the heavier fabrics of fall—try them with flannel trousers or selvedge denim, and you'll understand why Italian men have been doing this for decades. They also solve the perpetual problem of transitional dressing: too warm for boots, too cool for anything else. A substantial pair of loafers with proper socks (think merino wool, not cotton) bridges this gap perfectly.

But it's not just about practicality. The current state of menswear increasingly demands versatility, and few shoes deliver quite like a well-chosen loafer. They've moved well beyond their preppy roots, now equally at home with tailoring or more contemporary silhouettes. The key is choosing the right pair—and that's where we come in. Below, find 20 fine and fall-friendly loafers for men.

Ferragamo Funes Leather Penny Loafers

Hand-stitched in Italy, Ferragamo's Funes loafers exude black leather sophistication that makes a smooth operator out of anyone. Pair these black loafers with a formal suit for a more dressy occasion, or add polish to a jeans-focused casual outfit. The rubber sole keeps you grounded, just in case the compliments get to your head.

$880, shop now

Ferragamo. Ferragamo

G.H. Bass & Co. Men's Larson Lug Weejuns Loafer

G.H. Bass & Co., the creators of the world's first pair of penny loafers—the Weejuns—present the black Larson '90s style as a modern reinterpretation, thanks to a slightly thicker and sturdier rubber lug sole than the originals. This men’s loafer, crafted from smooth leather with a penny bar strap and apron-stitched front, is set on a sturdy welted midsole and rubber EVA outsole.

$185, shop now

G.H. Bass. G.H. Bass

Gucci Horsebit 1953 Loafer

The 1953 Horsebit loafer is what happens when equestrian hardware meets Italian swagger. This is Gucci's greatest hit, remixed for modern feet but keeping that gold bit that's been turning heads since JFK was president. The flat sole keeps things understated while that iconic hardware does all the talking.

$990, shop now

Gucci. Gucci

Loro Piana Travis Loafers

Leave it to Loro Piana to make English heritage look Italian. The Travis takes traditional British loafers and adds a chunky lug sole that's basically a suspension system for your feet. The calfskin leather has a "perfectly imperfect" finish—like your third-day stubble, but for shoes. They've managed to make something both rugged and refined, which is the footwear equivalent of ordering scotch at a wine bar.

$1,150, shop now

Loro Piana. Loro Piana

Sabah Fort Worth Brown Sabah Slip On

Handmade by master craftsmen in Gaziantep, Turkey, these casual shoes draw inspiration from a traditional slip-on loafer from the same region. The durable leather uppers, cut from premium cowhides, are hand-sewn by some of the country's finest shoemakers, boasting a tradition that dates back to the 1880s. The uppers are stitched to the rubber soles with a continuous waxed cotton thread, ensuring durable construction and lifelong resoleability for these slipper-style loafers.

$210, shop now

Sabah. Sabah

Adelante Luca Loafer

The Luca Loafer, handcrafted by local cobblers in Guatemala using premium full-grain leather, stays true to the original Norwegian penny loafer design. With its clean, easy-wearing silhouette, it's the perfect shoe to slip on in the morning and wear all day long.

$335, shop now

Adelante. Adelante

Valentino Garavani V Logo Leather Loafers

Experience the mastery of Italian shoemaking with Valentino's high-quality loafers. Crafted from grainy calfskin, these shoes exude chilled-out sophistication. The gold-toned V Logo adds an air of aristocracy, while the tawny hue creates a sublime sartorial narrative.

$1,090, shop now

Valentino. Valentino

George Cleverley Joey Full-Grain Leather Penny Loafers

Imbued with a debonair charm, these handcrafted navy full-grain leather penny loafers are as comfortable as they are dashing. Marrying sustainability with style, the ingenious soles are crafted from virgin hevea milk, yielding an ethereal microstructure that cradles your feet.

$565, shop now

George Cleverley. George Cleverley

Grenson Merle Loafers

These tassel loafers, meticulously sculpted in toffee-brown suede, are as luscious as aged scotch. Using Grenson's signature last shape, the Merle will carry you in subtle sophistication while the rubber grips on the leather sole harmonize practicality and grace.

$460, shop now

Grenson. Grenson

Quoddy Rover Penny Loafer

This artisanal made-in-Maine marvel boasts a formidable moc-toe silhouette, adding an indomitable spirit to an eternal classic. Swathed in premium leather, the hand-stitched moccasin construction envelopes your feet in supple luxury. Breathable and perfect for a sockless escapade, Quoddy's Revive insole is an ode to quintessential Americana craftsmanship.

$279, shop now

Quoddy. Quoddy

M. Gemi The Filare

This Italian-made classic penny loafer is constructed in the hills of Tuscany of supple, hand-burnished calf leather. The tonal stitching and grosgrain binding create moments of aesthetic interest, embodied by M. Gemi's impeccable attention to detail.

$278, shop now

M. Gemi. M. Gemi

Rothy's The Ravello Loafer

Rothy's new Ravello Loafer is a sustainable choice that doesn't skimp on comfort. The knit upper and cushioned insole are like a hug for your feet. Plus, these comfortable loafers are machine-washable. Who said you can't have it all?

$189, shop now

Rothy's. Rothy's

John Lobb Lopez New Standard Leather Penny Loafers

The Lopez New Standard are heirlooms for your feet: storm-welted construction, hand-stitched aprons and a reinforced round toe that laughs in the face of autumn puddles. That dark brown leather will develop a patina unique to your adventures (or misadventures). Yes, they cost as much as a decent watch, but unlike that timepiece, these won't need battery changes.

$1,780, shop now

John Lobb. John Lobb

Brunello Cucinelli Suede Penny Loafers

From Solomeo, Italy's temple of cashmere, comes a loafer that's basically a cardigan for your feet. Cucinelli's charcoal suede loafers master the art of being noticed without trying—like that one friend who never seems to dress up but always looks impeccable. The leather trim isn't just for show; it's there to remind you that even Italian casualness requires structure. Rubber-crepe soles mean you won't slip while slow-walking past store windows to check your reflection.

$1,100, shop now

Brunello Cucinelli. Brunello Cucinelli.

Bottega Veneta Bumper Leather Loafers

Bottega took one look at traditional loafers and said, "Let's give them platform shoes." The result? Bumper loafers with stacked soles would make a '70s disco dancer jealous. In black leather, they're business in the front, party in the profile. Think of them as your secret weapon for adding an inch of height without anyone knowing why you suddenly tower over Karen from accounting.

$1,200, shop now

Bottega Veneta. Bottega Veneta

Vinny's Belgee Glossed-Leather Loafers

Finally, patent leather that doesn't need a full-time butler. Vinny's Venetian loafer-inspired Belgees come in Polido leather—a material so low-maintenance it makes succulent plants look needy. The waterproof finish means you can wear these to garden parties without checking the weather forecast first. A soft cloth and polishing glove are all you need, which is perfect for those of us who think shoe care shouldn't require a YouTube tutorial.

$400, shop now

Vinny's. Vinny's

Todd Snyder x Rubinacci Marphy Loafer

When American pragmatism met Italian flair, they had a baby and named it Marphy. Mr. Luca Rubinacci designed these after failing to find formal dress shoes comfortable enough for his lifestyle, proving that sometimes the best innovations come from personal frustration. They're hand-made in Italy, which means each pair has probably seen more olive oil than your kitchen.

$475, shop now

Todd Snyder. Todd Snyder

J.M. Weston 180 Leather and Suede Penny Loafers

Named for the 180 steps in their production—because apparently 179 just wasn't enough—these French-made loafers are what happens when perfectionism becomes a business model. Since 1891, J.M. Weston has been making shoes in Limoges with the same attention usually reserved for fine porcelain. Goodyear-welted construction means they can be resoled until your grandkids inherit them.

$1,015, shop now

J.M. Weston. J.M. Weston

Christian Louboutin Chambelimoc Loafers

Louboutin looked at penny loafers and made them rock 'n' roll. The result: the Chambelimoc, featuring a removable silver pin that's basically fancy jewelry for your feet. The signature red sole ensures everyone behind you knows exactly what you're wearing, while the calf leather upper keeps things classic up front.

$1,195, shop now

Christian Louboutin. Christian Louboutin

Church's Lynton Leather Penny Loafers

Church's has been making shoes in Northampton since before your great-grandfather was comparing things to what his great-grandfather did. The Lynton takes that heritage and adds just enough modern attitude to keep things interesting with a raised apron, robust silhouette and thick rubber sole.

$1,150, shop now

Church's. Church's

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