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. 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.
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. Intimidating though they might be on the surface, you can certainly make the loafer work for you. Start your shopping with our WERD-approved picks below.
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 brands that helped bring the style to the forefront. These loafers are still made much the same way, with rich leather that tends to look even better when polished to a nice shine. And for the sub-$150 price tag, they’re might not be a more quality pair on the market.
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.
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. No matter how much or how little you drive, though, these shoes are a refined and elegant splurge you can wear with off-white 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. 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.
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. 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.
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. 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 ‘em easily with chinos or trusty stretch cotton chino shorts.
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