The Best Men's Loafers to Wear This Fall

L’Asola is one of the most iconic styles of Italian heritage brand Ermenegildo Zegna. The impeccable craftsmanship that goes into producing a pair is visible in the details: hand-stitched buttonhole band, low heel and flexible leather sole with concealed stitching, and a slightly elongated almond toe. The shoe is constructed in reverse, meaning the upper and leather lining are stitched onto the sole and then the shoe is unfolded on itself. This creates an incredibly flexible loafer and as the brand claims, it’s “the most comfortable slip-on you’ll ever wear.”

Shop: $695

Designer Adam Derick of To Boot New York always puts the quality of his shoes first. That’s why he only sources French and Italian leathers that are hand selected and hand-cut. Then the shoes are constructed in Italian factories according to the country’s shoe-making traditions.

And there’s definitely a stylish, dolce vita vibe coming out of these Raleigh suede loafers. Crafted from supple calf suede, they are hand stitched with leather soles. For the ultimate Italian peninsula-inspired look, wear them without socks.

Shop: $350

For Italian designer Gianvito Rossi, shoemaking is a family affair. After having worked in his father’s factory for 20 years (his father is none other than Sergio Rossi who also inherited the trade from his dad), Gianvito launched his own label in 2006. Fast forward 12 years, and the youngest Rossi is on top of the fashion world. His approach to fashion is simple: good design doesn’t need to overwhelm with bells and whistles. He puts attention to quality first and continually works towards delivering a product that’s better than the last one.

This loafer crafted in Italy from rich suede in a dark olive shade delivers everything Rossi is known for. The slip-on style has a classic almond toe, a padded insole, a leather sole, and a covered block heel. You can dress them up by styling them with a suit or wear them during the weekend with a pair of slacks.

Shop: $795

During his days at the helm of Gucci, Tom Ford’s name became synonymous with sex appeal. Now that the designer has his own label, things haven’t really changed much. Even for his menswear line, Ford doesn’t shy away from the racy and provocative—all in a very sophisticated way, of course. Sequined and shiny smoking jackets in animal prints and snakeskin pants were part of his first men’s runway show earlier this year.

Naturally, he has designed the shoes to match his risqué aesthetic. These loafers are crafted from hand-polished ‘cracked’ patent leather in Italy. They feature gold-toned chains, leather lining, and a .6-inch heel. We love a classic pair in black, but they are also available in four more colors—brown, olive green, cobalt, and light blue.

Shop: $1,490

While some brands prefer to put their logo on all their products, others rely on patterns and fabric manipulation techniques that have become synonymous with their name. One such brand is Bottega Venetta. The company came up with their iconic Intrecciato weave because of simple necessity. When the company started creating accessories in a region known for its ready-to-wear production, the Bottega Venetta craftsmen had to come up with a technique that made the fine leather they were forced to use (because the sewing machines were designed to work with cloth) sturdier. And that’s how Intrecciato was born.

So you can rest assured—these loafers are stronger and more durable than a regular pair of shoes. They have a square toe and are completely lined in leather. And the overall Intrecciato pattern adds a touch of old world elegance to them.

Shop: $810

Salvatore Ferragamo has always been the quintessential Italian brand, favoring impeccable tailoring, traditional techniques, and quality materials with a touch of Italian flamboyance.

And this suede loafer is just as dapper as it is the perfect example of the Florence-based company’s craftsmanship. Made from soft calfskin suede, it has an almond-toe silhouette with decorative stitching details. The gold-tone hardware elements are engraved with the brand’s name and connected by a knotted strap—a nice, creative touch to this classic design.

Shop: $630

For those cool fall weekends, opt for a shoe that’s equal parts casual and elegant. The new version of Cole Haan’s Pinch Weekender LX is constructed with a higher sidewall profile that has a reinforced tapping at the toe, which makes it sturdier and appropriate for a variety of terrains.

This shoe is all about delivering maximum comfort. The molded perforated footbed has added heel cushioning and a secondary layer of memory foam.

The cool detailing on this loafer is worth mentioning too—the tonal stitching, custom twill lining, and lobster logo contribute the shoe’s casual vibe.

Shop: $140

Gucci started off as a luggage company in Florence, but is now one of the top 3 most valuable luxury brands in the world with its shoe business accounting for almost 20 percent of overall sales. The company’s painstaking attention to detail and commitment to impeccable quality is probably to “blame” (not that we’re underestimating the flamboyant design vision of its creative director Alessandro Michele).

In fact, if there’s a brand that knows how to make loafers, that’s definitely Gucci. After all, the company is often credited with the creation of this formal style that dates back to the 1950s.

The Donnie Web loafer channels the timeless silhouette that first made this shoe so popular. It features the brand's signature two interlocking G’s that embellish the green-and-red strap. An elongated apron toe and a stacked heel contribute to this slip-on style’s classic vibe.

Shop: $730

While loafers are traditionally a formal type of footwear, one that you would normally don in the office or at an official event, “drivers” are their more casual cousins and are better suited for weekends.

Prada’s shoemakers follow a 200-step process to create each of their driving shoes, which means you are getting the absolute best in terms of quality and craftsmanship.

This Prada “Penny” shoe has a classic loafer silhouette—it’s crafted from navy saffiano leather and finished with the company’s logo and tonal stitching. It also has a lightly padded sole for added comfort.

The most distinctive part of driving shoes are the soles. Rubber pods that reach all the way to the lower part of the heel deliver superior grip and flexibility.

Shop: $550