The 7 Most Comfortable Pairs of Dress Shoes for Men

The 7 Most Comfortable Pairs of Dress Shoes for Men

You've spent well over four figures and countless hours buying a suit, getting it tailored, and picking out the perfect shirt and tie. Nice work, you look great! But the wrong (read: uncomfortable) pair of dress shoes can ruin your entire look. Nobody looks polished while they're in pain. All dress shoes are not created equal, but there are lots of fashionable options that look and feel good on your feet. Look for real leather, stitched soles, and high quality lining. More importantly, try them on and walk around to break them in a bit to make sure they're comfortable on your feet. Read on to shop our seven most comfortable pairs of men's dress shoes—plus our tips on how to store and pack them. Don't you look smart?

See recent posts by Charles McFarlane

Our Favorite Dress Shoe Picks for 2019

Most Comfortable Dress Shoe: Under $100

Jemison Cap Toe Derby STACY ADAMS
A cheap pair of dress shoes can be your worst enemy. They’re likely to rub in all the wrong places (hello, blisters) and fall apart after a few wears. But if budget is an issue, then go for the Stacy Adams Jemison Cap Toe Derbies. They’re made from buffalo leather, known for its strength and elasticity, and look particularly lustrous, which is code for expensive. The derbies also feature a lace-up closure and memory foam footbed to help you stay comfortable on your feet. Looking good and saving money, is there anything better?

$100 at Nordstrom

Most Comfortable Dress Shoe: Most Five-Star Reviews

Allen Edmonds Men's Park Avenue Cap Toe Oxfords
For the research obsessives out there (welcome to our club), the Allen Edmonds Park Avenue Cap Toe Oxfords are it when it comes to well reviewed comfortable dress shoes. It’s no surprise Allen Edmonds—who has been crafting shoes in the USA since 1922 using a 212-step crafting process—would rack up almost 700 five-star reviews on Bloomingdale’s. Fanatics rave about everything from the incredible customer service to the high quality craftsmanship to the all-day comfort—lots of gentlemen own several pairs. With a 360-degree Goodyear welt construction (which means they can be resoled over and over again) and timeless design, your Allen Edmonds shoes may outlast the best of us.

$425 at Bloomingdale's

Most Comfortable Dress Shoe: Loafer Style

Cole Haan Men's Pinch Grand Classic Penny Loafer
When you’re traveling or flying, it’s good to have the option to easily kick off your shoes—especially at TSA. This ease is exactly what the loafer was made for. While there are many varieties out there, the king of the loafer will always be the penny loafer. The Cole Haan Pinch Grand Classic Penny Loafer is about as classic as you can get, but with a few modern tweaks. A low heel and three leather finishes look stylishly preppy. The molded EVA footbed, leather sole, and light lining make them a dream to walk in. Actually, you may never feel like kicking them off.

$200 at Cole Haan

Most Comfortable Dress Shoe: Laced Style

Brooks Brothers Golden Fleece® Cordovan Captoes
When you close your eyes and think of a dress shoe, you probably imagine the cordovan cap toe. It’s a classic silhouette with a stitched seam on the toe, that simply looks elegant and fashion forward, regardless of what else you pair it with. And if you’re going to buy a well-made classic that’s meant to last, go straight to Brooks Brothers. As part of their Golden Fleece line, these Cordovan Captoes are crafted in Italy and feature a beautifully made lace closure. The Ortholite insole, leather outsole with a slippage-preventing rubber insert, and Goodyear welt construction are worth the price. These are the kind of shoes you should get married in.

$748 at Brooks Brothers

Most Comfortable Dress Shoe: Lightweight

Cole Haan Feathercraft Grand Blucher Oxford
Lightweight shoes are your best friend on the go. Not only do they feel footloose and fancy free while you wear them, they keep your suitcase light while they’re packed. Cole Haan’s Feathercraft Grand Blucher Oxfords are just one pound. They’re made from smooth suede or classic leather (available in four colors) and will look equally good with a pair of nice jeans as they would with a tailored suit. The injected Grand.0S energy foam in the midsole ensures lightweight cushioning superior and energy return is just what the name implies. These really are light as a feather—a blessing when you are running to make your connecting flight.

$179 at Zappos

Most Comfortable Dress Shoe: Most Support

Men's Signature Handsewn Jackman Blucher Mocs, Leather L.L.Bean
While you can stray on dress shoe form, you do need to consider function. And for the best function you can’t beat the American stalwart, L.L. Bean. When worn with sharp jeans or well tailored (no break) cords, these Blucher Mocs strike the right balance between rugged and polished. These bluchers can take a real beating and are crafted to take it, with sturdy hand sewn full-grain leather and rawhide laces. The molded rubber outsole offers extra support.

$99 at L.L. Bean

Most Comfortable Dress Shoe: Statement Style

Burberry Brown Suede Solway Loafers
Dress shoes should be fun, and they can definitely make a statement while staying comfortable. Burberry’s brown suede Solway Loafers are butter soft and the gold chain-link detail is sure to turn heads. You can wear these with socks and a suit, or go more relaxed and Miami-style, and skip the socks completely.

$680 at Ssense

How to Store Dress Shoes Properly to Extend Their Life

Now that you’ve settled into a comfortable pair of dress shoes or two, you need to take care of them. It’s tempting to just kick them into the closet and forget about them until the next special occasion, but there’s a better way. Take a few simple steps to greatly improve your shoes’ lifespan.

Shoe Trees

Woodlore Adjustable Men's Shoe Tree Pair
First, get yourself a pair of cedar shoe trees. If your dress shoes aren’t on your feet, they should be parked on an adjustable cedar shoe tree. Not only do they keep your leather shoes in good shape, they absorb moisture and reduce foot odor.

$17.99 at Amazon

Charcoal anti-odor inserts

Jason Markk Cedar Shoe Freshener
If you’re partially prone to odorous shoes, throw some cedar shoe fresheners into the mix as well. These Jason Markk small sachets filled with cedar shavings absorb odor and moisture. Bonus: they also deter moths and insects. Gently shake periodically to release aromatics as needed over time.

$12 at Need Supply Co.

Shoe Polish

Cole Haan Mini Deluxe Travel Kit
Every man should have a shoe shine kit. This version, by Cole Haan, is perfectly sized to take with you on your travels. It comes with all the accoutrements, from thee colors of shoe cream to a buffing brush and shine sponge, in a handy leather bag. Use it with regularity, and your shoes will look fresh for years to come.

$40 at Cole Haan

How to Pack Dress Shoes for Travel 

When packing your dress shoes, follow a few simple rules. Always place them at the bottom of the bag, for best weight distribution and to keep your shoes away from clean clothes. Pro-tip: place rolled socks in your shoes to help with form. If your shoes are particularly dirty, place them inside a shower cap, and always pack dress shoes in shoe bags.

Shoe Bags

Herschel Supply Co. Shoe Bag Set in Black
Many dress shoes come with a shoe bag to help with storage and transportation, but it’s smart to have some high quality shoe bags on hand. Herschel makes a chic black set, helpfully labeled, “shoe bag.”

$20 at Need Supply Co.

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