Picture this: balmy summer days, linen suits, chilled cocktails and the radiant sun kissing your skin. Now, glance down—what’s gracing your feet? If the answer isn’t a sleek pair of loafers, prepare to take notes.
Loafers, my good sirs, are the epitome of suave with a sprinkle of nonchalance—think James Bond on a day off. Rooted in the rugged charm of Norwegian farmer’s footwear, the loafer has since evolved into a symphony of style and versatility. It’s like a martini for your feet—shaken, not stirred.
First up, the classic penny loafer. Legend has it that the shoe’s design snugly housed a penny—just enough for an emergency call back in the day. It soared in popularity in the 1950s and ‘60s, embracing a devil-may-care attitude, with or without socks. Part of the post-war Ivy League look, it’s been an enduring symbol of preppy chic.
And let’s not sideline the humble moccasin. Traditionally crafted from a single piece of leather wrapping the foot and uniting at the top, today’s moccasins are your go-to for understated elegance. They whisper comfort and whisper it well. Then there’s the tassel loafer, an icon that laughs in the face of obsolescence. Tassels dance on its vamp, making it the sartorial choice for those looking to strike the delicate balance between the relaxed and the refined. It’s the dark horse that pairs with everything, elevating the everyday and toning down the overly formal.
Each loafer variant adapts itself chameleon-like to a different dress code, making them the nonpareil choice in men’s footwear. From the business boardroom, to casual beachside margaritas, to the yacht deck soiree, the right loafer is your passport to panache. Here are 15 pairs that should be on your radar.
Subscribe to Observer’s Lifestyle Newsletter
All products featured are independently selected by Observer editors. When you buy something through our links, we may earn an affiliate commission that supports our work.
The Best Men’s Loafers
From casual loafers to dressy slip-ons and driving shoes, these are the best loafers for men.
Le Majordome M08 Penny Loafer
Le Majordome’s M08 Penny Loafer is where sartorial savviness meets Swiss precision. Its apron front whispers tradition, while hexagonal punching shouts innovation. High-quality French calfskin in rich dark brown holds court here, and bespoke aficionados, take note: customization of these goodyear-welted loafers and over a dozen other styles is the name of the game at their Swiss and NYC showrooms.
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 or add polish to a jeans-focused casual outfit. The rubber sole keeps you grounded, just in case the compliments get to your head.
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 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.
Gucci Jordaan Horsebit Suede Loafers
The Gucci Jordaan is your passport to la dolce vita. With its slim toe, suede finish and iconic horsebit detail, it’s luxury distilled into a shoe. Since the introduction of its classic shape in the 1950s, the preppy-inspired Gucci horsebit loafer has continued its influence, redesigned in new forms and materials. These are perfect for the man who knows his Fellini from his Godard.
Tom Ford Woven Leather Neville Loafer
The Neville Loafer is Tom Ford at his finest. With woven leather that whispers luxury, and a penny slot that nods to tradition, this dress shoe is for the gentleman unafraid to leave a lasting impression.
Loro Piana Sea-Sail Walk Loafers
Set sail with style in Loro Piana’s take on the traditional boat shoe. These lace-up suede shoes offer a seafaring twist on a classic. Crafted from prime cut hide, they exude luxury, while a water-repellent finish keeps you dry. Perfect for sailing or beachside lounging, these loafers combine comfort and versatility.
Sabah Fort Worth Brown Sabah Slip On
Handmade by master craftsmen in Gaziantep, Turkey, these casual shoes draw inspiration from a traditional slip-on shoe 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.
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.
Brunello Cucinelli Loafers With Tassels And Natural Rubber Sole
Exquisitely fashioned in the enchanting hamlet of Solomeo, Perugia, the Brunello Cucinelli tassel loafers are an opulent alchemy of Italian sartorial finesse. These pieces of art are sculpted from a velvety suede that molds to your feet, and a featherlight natural latex outsole. Subtle logo lettering is emblazoned on the footbed.
Valentino Garavani V Logo Leather Loafers Leather Loafers
Experience the mastery of Italian shoemaking with Valentino’s 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.
George Cleverley Joey Full-Grain Leather Penny Loafers
Imbued with a debonair charm, these handcrafted full-grain leather penny loafers, available to shop from Mr Porter, 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.
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.
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.
M. Gemi The Filare
This Italian-made 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 that embodies M. Gemi’s impeccable attention to detail.
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?