Lace Up With This Selection of the Best Wingtip Boots for Every Occasion

Best Wingtip Boots

Lace Up With This Selection of the Best Wingtip Boots for Every Occasion

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The idea of literally stepping into a new year in style has never been more important, or easier to achieve, and that’s especially true when you consider the best wingtip boots for men. Revamping your style in the throes of winter can be difficult when you’d rather slide into a pair of the comfiest at-home pants and lounge by the fire.

That being said, getting out and about in the world (and back to the office, and back to your favorite watering hole) requires something a little stronger and more stylish than slippers, even if you’ve found your favorite pair. Wingtip boots are a historic throwback (the perforations were originally useful in navigating wet ground in the Scottish Highlands), yet they’re surprisingly modern, functional and refined today.

RELATED: Best Winter Boots for Men

You’ll find options made from rich leather to team nicely with your favorite winter wool suit, as well as picks that wear well with chinos and jeans. Wingtip boots are more elegant than work boots, so they also pair up with office-ready and date night-friendly looks. And when you want to go more rugged with a cozy sherpa trucker jacket and slim black jeans, wingtip boots have your back. That is, when you’ve got the right pair — and we’re here to offer our suggestions accordingly, so lace ‘em on up and get out there this winter.

Allen Edmonds Dalton Wingtip Dress Boots

Allen Edmonds

Perhaps Allen Edmonds comes to mind right away when you think of stylish dress boots and shoes, right? They’ve been making refined and durable shoes in the U.S. for decades, after all. The Dalton Wingtip Boots are an impressive pair, with a sleek profile, a rich variety of leather options and the sort of design to be worn with jeans or a houndstooth winter suit in equal measure.

$399 at

Johnston & Murphy XC Flex Cody Wingtip Boots

Johnston & Murphy

When you want to toe the line (pun intended) between dressy and sharp yet comfortable, Johnston & Murphy frequently has you covered with its full line of dress shoes and sneakers. Here, they’ve translated that same technology into handsome wingtip boots featuring the brand’s XC Flexconstruction rubber outsole for a smooth ride and a grippy finish.

$198.95 at

Thomas & Vine Ryker Wingtip Boots

Thomas & Vine

For under $100, amp up your style in a sharp way with black leather wingtip boots that call to mind a pair that might be worn by the famed (fictional) British gangster Tommy Shelby in Peaky Blinders. The side zip detailing is visually interesting and makes them easy to step into when wearing thicker boot socks or dress socks. All that’s missing now is a grey tweed suit, an overcoat and a dram of whiskey.

From $89.99 at

Wolverine BLVD Wing Tip Boots


We’re willing to bet you know Wolverine’s famed work boots and plain toe leather boots quite well at this point, but what about the dressy-yet-still-rugged BLVD line? These are day-to-night boots to wear with everything from plaid wool dress pants and a cardigan to a rugged denim shirt and a thermal henley (cold beer at your favorite bar sold separately).

$199 at

Bruno Marc Dress Ankle Motorcycle Boots

Bruno Marc

You might not think of normally dressy wingtip boots as the sort of boots you can wear on the open road, but this affordable pair from Bruno Marc is built differently. The flexible rubber outsole actually absorbs vibrations and shock, and the sleek build wears well with slim moto jeans in any color.

From $42.99 at

Thursday Boots Wingtip Boots

Thursday Boots

Thursday Boots is as well-loved a men’s boots brand as any on the market, blending premium quality with agreeable pricing. That remains the case with these wingtip boots, the kind you can wear with chinos and a chambray shirt at the office, or with a thermal henley and slim black jeans on the weekend. The hand-finished full-grain leather is particularly impressive, and should break in nicely over time.

$235 at

Barbour Seaton Wingtip Boots


Barbour’s name is nearly unmatched when it comes to fashioning rugged gear for road trips and blustery weather in equal measure. That’s what makes these durable wingtip boots such a fitting complement to the brand’s waxed cotton outerwear. A blend of leather and textile on the upper gives them plenty of added toughness for both the city and the country.

$230 at

English Laundry John Wingtip Boots

English Laundry

It’s unique to see a pair of the best wingtip boots with a “longwing” design, where the wingtip detailing extends down the length of the shoe. In the case of these handsome burnished wingtip boots, the effect definitely works, turning them into an eye-catching pair of wear-with-anything dress boots.

$200 at

Gordon Rush Sutherland Wingtip Boots

Gordon Rush

Fine craftsmanship at an agreeable price can be tricky to come by at times, but with Gordon Rush, you get luxury-level quality without breaking the bank. The Sutherland Wingtip Boots, which are more of an ankle boot than a taller lace-up, drive home this point quite nicely, blending a premium leather upper (and a sharp traditional black colorway) with a sub-$300 price tag.

$295 at

TAFT Boots Wingtip Boots

TAFT Boots

Lacing up your boots for winter doesn’t have to be all about work. TAFT proves that quite handily with this fun and eye-catching pair of mixed-media wingtip boots, blending a hard-wearing Vibram sole with a handsome blend of rich leather and plaid wool detailing.

$236 at

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