Some menswear styles have the distinction of being easy to wear–almost too easy to wear: Canvas sneakers and lace-up leather boots come to mind. But loafers? Loafers are, at first glance, another beast altogether.
When I first started getting an interest in menswear (an interest that grows by the day!), loafers seemed intimidating – a classic all the same, but once I realized they were easier to wear than I thought, my wardrobe changed completely.
At once preppy (the penny loafer) and sleek (the driving loafer – more on those shortly), the best loafers are still as valuable a pair of footwear to have in your style rotation as any.
You needn’t fear the loafer. Think of them like a classed-up version of boat shoes as a starting point–the same styles that work with your trusty boat shoes can work just as well when styling a look alongside the men’s loafer. The loafer is infinitely classic and can be worn like dress shoes as well as those aforementioned boat shoes.
So, your breezy linen pants or olive chinos, paired up with a white or navy polo? Yes, those work with brown leather loafers. Or a pair of chino shorts and a simple navy short-sleeve button-down? Go ahead, wear your new favorite loafers and join me in the quest for classic-yet-modern style. Intimidating though they might be on the surface, you can certainly make the loafer work for you.
Start your shopping with my WERD-approved picks below.
Oliver Cabell delivers designer-quality shoes at prices that reflect its direct-to-consumer system, passing the savings onto its customers. That’s what we love about Oliver Cabell’s crisp, textured leather penny loafers, which are made with Italian leather atop a comfortable rubber outsole. Dress them up with a summer suit or dress them down with chino shorts and a henley.
The penny loafer is a traditionally preppy style made modern in the hands of luxury footwear maker Oliver Cabell.
Don’t let the luxury tagline scare you off, though: These are well-made and yet priced accessibly (especially when on sale), and the rich, dark leather makes them a more neutral footwear option that’s easier to style if you’re just diving into the world of loafers. Feel free to wear these with everything from rolled light wash jeans to a khaki cotton suit.
It doesn’t get more timeless than the penny loafer, and you might say that no one does it better than G.H. Bass & Co., one of the men’s clothing brands that helped bring the style to the forefront.
For my money’s worth and in my experience, these penny loafers are as classic as it gets – they were the very first pair of loafers I bought, and I still have them to this day.
These loafers are still made the old-fashioned way, with rich leather that tends to look even better when polished to a nice shine. And for the sub-$150 price tag, there might not be a more quality pair on the market.
While you might typically associate Huckberry with rugged gear like leather boots and waxed trucker jackets, the famed retailer has a softer side, quite literally.
The Huckberry team first tracked down Italian-made Astorflex shoes years ago, and often sells out of its buttery-soft chukka boots. The same carefully considered, surprisingly refined construction and design shines through with these loafers, which feature soft European leather and a durable rubber heel for added traction. Wear them from day to night for breezy coastal style.
The classic loafer gets a modern update in the hands of Cole Haan, which blends the best of sports-minded footwear technology with the sleek profile of a penny loafer.
I personally love the springy comfort and dependability of Cole Haan shoes, especially the blend of sneaker innovation and sharp loafer style.
There’s plenty to be said for brown leather loafers with a classic design, but black loafers signify style that’s a touch more elegant and dressy from time to time, and there’s nothing wrong with that, either.
This particular pair comes from a slightly unexpected source: Clarks, a brand you know – and I know – from making some of the best chukka boots around. The Markman loafers are more of a driving-style loafer, with a grooved outsole and a flexible, lightweight design. Wear them on the open road all spring and summer long.
Also available in brown or tan if you are looking for something a touch more casual.
When you’re not quite sure where to start when wearing loafers, it’s best to go with a classic: Turn to the makers of your tried-and-true boat shoes, for instance.
The Sperry Gold Cup, in my experience, improves even upon Sperry’s already-famous loafers and boat shoes with even better materials more durable design and timeless style. Needless to say, I’m a big fan and have loved breaking mine in over the years.
Sperry steps things up a notch with a handsome pair of made-in-America leather loafers made from Horween leather out of Chicago and then set atop a contrasting white sole for a more casual look.
They’ll break in nicely over time, thanks to the rich brown leather, and you can wear them easily with chino pants or trusty stretch cotton chino shorts.
Feel like splurging on a pair of loafers? It’s hard to go wrong with a luxury brand that pioneered the tricky category of driving shoes–shoes you can slip on at a moment’s notice to go for a coastal drive, outfitted with a handy pebbled outsole for added traction.
For me personally, Tod’s loafers are as well-made as it gets, with luxury quality, soft construction and comfort that you can really feel when you slide into them.
I even recommend wearing them with off-white or natural denim or olive linen trousers for a touch of Euro-inspired style.
No matter how much or how little you drive, though, these shoes are a refined and elegant splurge you can wear with jeans and a navy polo for an eye-catching evening look.
Here’s the thing about wearing a pair of the best loafers for men: You can style them exactly as you please, provided you do it the right way – and that includes with dressy tailored looks like a blue tropical wool (or all-season wool) suit, as well as linen trousers or chinos for a can’t miss business casual style. And while these tassel loafers are a bit more bold, the quality is exceptional and the styling potential is limitless.
For under $100, make your way into the world of loafers with a crisp, dressy and sharp black leather option from Nordstrom.
Black leather turns the loafer into a clean dress shoe, the kind you can wear with a navy suit or use as an anchor to more bold colors, like an olive or mid-blue cotton suit at your next summer outdoor wedding. And if you want to wear loafers to the office, black is a solid move that keeps things nicely grounded.
Not every loafer has to closely resemble the classic penny loafer. Some can take on an aesthetic that’s similar to a warm-weather-minded espadrille shoe, for instance, and that’s what Nisolo has done with this visually appealing woven loafer.
It helps that they’re also water-resistant and designed with a cushioned footbed for all-day comfort. These are shoes you can certainly wear with, well, just about any summer look you can dream up.
It’s really the small details that make the difference when you consider the best loafers for men, with handmade construction often signifying an intense attention to detail and superior quality.
That approach certainly checks out when considering the Adelante Luca Loafers, which are created in Guatemala by skilled craftsmen paid above the Living Well line in terms of wages.
The result is a richly built pair of loafers that will mold to your feet and develop a sharp patina the more you wear them – and you’ll want to wear them plenty often.
Personally, I’m a major fan of the rich leather and hard-wearing construction of Rhodes Footwear boots, which I tend to wear all fall and winter long with my favorite pair of blue jeans. And yet, this pair of streamlined-yet-rugged loafers should fit the bill perfectly for spring and summer from Rhodes Footwear.
The key is the use of comfortable-yet-strong rubber outsoles and a storm welt design for durability, not to mention a rich leather upper that will develop a very nice patina over time. Pair them with Flint and Tinder’s 365 Pants from Huckberry for season-long versatility.
Todd Snyder launched his brand with a focus on updating rugged classics in modern ways, like high-top sneakers by P.F. Flyers or some of the coolest sweatshirts on the market from Champion.
He takes the same nuanced approach to a more refined style this time around, the loafer – and the results are classically Todd Snyder (and made by a Snyder-approved brand, to boot).
The sleek suede upper is complemented nicely by timeless penny loafer construction by the English-made Sanders, which has been making some of the best footwear on the planet since the 1800s. For an investment-worthy style shopping splurge, go with this pair.