The Loafers That Perfect the Art of Transitional Dressing

The best loafers transcend seasons.

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The humble loafer is the rare shoe that transcends seasons. It's one of the most underrated footwear staples, and one that is just as suitable for pretty much any time of year—it all depends on how you style the timeless shoe. Still, there's no denying that loafers are especially suitable for those tricky transitional months, when you need to bid adieu to sandals but don't want to break out the boots just yet. So as summer starts to wind down and fall beckons on the horizon, let's put the spotlight back on loafers.

While certain loafer silhouettes have risen and fallen in popularity over the years (ahem, the lug sole), the overall concept is timeless. More elegant than a sneaker yet more comfortable than a ballet flat, the loafer is dependable and classic, but not dated nor frumpy.

Along with traditional styles like drivers and penny loafers, there are also plenty of modern iterations of the shoe. Leather and suede loafers never go out of style, but fresh takes include fabric options like patent leather and dressier velvets. Below, take a look at the best loafers ahead of fall.

Brunello Cucinelli Classic Suede Boat Loafers

Leave it to Brunello Cucinelli to make the oh-so American boat shoe silhouette into a pair of loafers with decidedly Italian flair. The streamlined silhouette, soft suede and the brand's signature monili detailing on the laces adds a feminine edge to the traditionally masculine shoe, while leather lining and a lightweight rubber sole ensure comfort and a touch of practicality.

$1,190, shop now

Brunello Cucinelli. Brunello Cucinelli

Tod's City Gommino Driving Shoes in Suede

You can’t talk about loafers without a major shoutout to Tod’s. The Gommino suede shoe is nothing short of iconic, and now comes in a plethora of different materials and colorways. But let's be real here: If you're going with Tod's, keep it classic. These driving loafers come in a camel suede for a plush texture that doesn't skimp on style.

$775, shop now

Tod's. Tod's

Thursday Boots The Penny

Lug sole loafers soared in popularity a few years ago, and they’re not going away anytime soon. This classic black patent leather pair is a fun interpretation of the preppy shoe, with a platform that gives some extra height, but doesn't result in a costume-y, over-the-top chunky heel.

$140, shop now

Thursday Boots. Thursday Boots

Margaux The Astor

Handcrafted in Spain, Margaux's Astor shoe combines the best of the classic loafer with a breezy mule. Polished enough to wear to the office, effortless enough to wear with shorts and T-shirt on vacation.

$395, shop now

Margaux. Margaux

Belgian Shoes All Calf Midinette

Belgian loafers have been owning the quiet luxury space since before the term existed. These shoes are the epitome of "if you know, you know," and can't even be purchased online—instead, you'll need to go to the brand's petite New York City boutique, but we promise it's worth the effort, as you'll be perfectly fitted into the best size and style shoe for your foot. Hand-stitched in Belgium with a rubber sole and the brand's signature bow tie on the vamp, these shoes have been around since the 1950s, when Henri Bendel's nephew first began selling them in his uncle's department store, and then in a separate storefront. The style has pretty much stayed the same as when the loafer was first produced in the 1950s, because why mess with a classic?

$675, shop now

Belgian Shoes. Belgian Shoes

Gianvito Rossi Patent Platform Penny Loafers

For the woman who refuses to go out without a heel, might we suggest these glossy patent leather penny loafers? A three-inch block heel adds height without sacrificing comfort, and also lends a touch of drama to the traditionally preppy shoe.

$1,095, shop now

Gianvito Rossi. Gianvito Rossi

Everlane The Modern Loafer

Everlane's menswear-inspired sleek leather slip-on is outfitted with a foam-cushioned insole for additional comfort. The stacked heel loafer is preppy but not overly so, with crisp stitch detailing and a tapered toe.

$168, shop now

Everlane. Everlane

Birdies Starling in Black Velvet

Looking for a casual, minimalist and genuinely comfortable loafer? Try Birdies—more specifically, this classic black velvet slipper, for a modern take on the smoking shoe.

$120, shop now

Birdies. Birdies.

Prada Triangle Logo Loafer

Prada’s low-heeled lug-sole loafers were a major part of the shoe silhouette’s resurgence, spotted on street style fashion-forward favorites including Kendall Jenner, Hailey Bieber and Bella Hadid. The versatile polished black leather shoes have a chunky, ridged sole and heel. Wear them with a low sock or tights when you feel a chill in the air.

$1,200, shop now

Prada. Prada.

Reformation Agathea Chunky Loafer

Reformation's platform loafers come in a few colors, but the taupe calf suede leather is an easy choice for autumn. The plush suede adds a softer touch to the chunky shoe.

$278, shop now

Reformation. Reformation

G.H. Bass Women's Whitney Weejun Loafers

If you want to try out the loafer trend but aren’t sure where to start, you can’t go wrong with the G.H. Bass Weejuns. This is, after all, the brand that created the first penny loafer in the 1930s. That's not to say that G.H. Bass is stuck in the past, though—the brand has kept up with fashion trends without losing sight of its high-quality craftsmanship and original ethos. The Whitney Weejun is made in El Salvador from premium box leather, with a hand-stitched traditional moccasin toe.

$175, shop now

G.H. Bass.

Loro Piana Suede Tassel Moccasin Loafers

Made in Italy, these suede moccasin loafers feature a water-repellent finish, rounded toe and rubber pod sole. Loro Piana always nails effortless luxury, and these slip-ons are no different, with sabot-style collapsible heels and a tassel.

$985, shop now

Loro Piana. Loro Piana

Gucci Brixton Horsebit Convertible Loafer

Gucci’s Brixton horse-bit loafers are another mainstay that are beloved by fashionistas and prepsters alike. Made in Italy, this updated version of the Gucci loafer features a collapsible heel, so you can style it as a slip-on mule, if you so choose.

$1,050, shop now

Gucci. Gucci.

Rothy's The Driver

Rothy’s knit slip-on loafers are inspired by classic driving loafers, and are both supremely comfortable and machine-washable. Even better, the eco-friendly shoe is made out of plastic water bottles.

$189, shop now

Rothy's. Rothy's

Sam Edelman Loraine Bit Loafer

The Loraine is a classic chain loafer; a best-seller for the brand. They come in a few different colors, and if you dare wear white after Labor Day (which, by the way, we are firm proponents of), try the lighter hue.

$150, shop now

Sam Edelman. Sam Edelman.

Franco Sarto Franco Carolynn Loafer

If you want a pair of patent leather loafers but aren't ready to splurge on a pricey version just yet, try Franco Sarto's slip-ons, with brown detailing, a lug sole and a tassel.

$110, shop now

Franco Sarto. Franco Sarto.

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