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.
Amberjack’s laser focus on crafting some of the most stylish and yet comfortable loafers on the market has made waves, and it’s a focus that has paid off handsomely, at least in my personal experience.
Amberjack loafers boast proprietary technology for hours of comfort and style.
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.
Understated elegance is something of a specialty for Meermin, which makes perfect sense when one considers its streamlined, perfectly shaped take on some of the best loafers for men.
More dressy than a classic penny loafer, these are elegant enough to wear with a lightweight suit.
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.
The result is a streamlined set of summer shoes made to be worn casually with tan chino shorts and a white pocket tee, or else breezy olive chinos and a white henley.
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.
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 shorts 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.
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.
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.
Allen Edmonds dress shoes have long exuded high-quality craftsmanship and versatile appeal, and when modern technology is added into the mix, some of the best men’s loafers round into form.
These boast an easy-on design, a handsome pebbled leather upper and the comfort of your favorite sneakers underfoot.
GREATS first debuted over a decade ago with highly affordable sneakers filtered through its Brooklyn headquarters. Its sense of style has only expanded since then, coming to a head with loafers that blend sneaker comfort and technology with polished refinement.
From jeans to chinos, these are a menswear winner in my book.
Although best known for its handsome, luxurious Italian sneakers, all areas of your footwear wardrobe are covered with loafers from KOIO.
Craftsmanship and quality remain paramount, with a handsome suede upper and a versatile, contrasting sneaker outsole for a smooth ride every step of the way.
The suede loafer adds texture and visual appeal to many an outfit, from summer suiting to breezy chinos, and this premium option from Grantstone (also makers of some of the best men’s boots) delivers on all fronts.
The streamlined take on the penny loafer is as high-quality as it gets, in my experience.
Perhaps you recognize heritage British footwear makers Grenson for its rugged-yet-refined combat, wingtip and dress boots.
Its loafers aren’t to be overlooked, with history and quality inherent in every stitch (not to mention the brand’s handsome, eye-catching pebbled leather uppers, a signature move).
FRYE is another brand prized for crafting some of the finest boots for men on the market, at least in my personal experience, and it’s hard not to be impressed by the durable-yet-elegant craftsmanship on display with its Mason Slip On Loafers.
With a crisp Venetian-style design, these are understated, dressy and worth the investment.