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The Best Men’s Wingtip Boots: From 1920s Gangster to Modern Boho Style

One of the guaranteed head-turners in men’s fashion is a statement-making boot. And while cowboy boots are trending and cap-toe boots are classic, perhaps no other style catches more eyes than the wingtip boot. According to Kory Stevens, Founder and Designer of Taft, the best men’s wingtip boots occupy a sacred space between dressy and casual attire.

“[A wingtip boot] combines and treads that line so well. A good wingtip boot/shoe can be worn on almost any occasion and not only fit in but also stand out with its intricate brogue detailing. It has a certain ruggedness stemming from its country origins that makes it a shoe that can do about anything,” Stevens explained.

An intricate and ornate style, wingtip boots are a derivative of the wingtip shoe, an icon from the Scottish Highlands, to which Stevens alluded. The original wingtip shoes featured holes that were carefully punched throughout the shoe to provide rapid drainage in an inevitably waterlogged Scotland that also allowed the shoe to dry faster. Today, this style is celebrated as one of the sharpest dress shoes amongst suited men.

Although wingtip boots are cool, owning a pair isn’t absolutely necessary — other styles can be worn. But rocking a pair comes with definitive upsides. One of the easiest ways to exponentially upgrade an outfit is by rocking a wingtip boot. This iconic, historic style offers a certain edge that isn’t found with a simple Chelsea boot or a bulky work boot. They’re much more attractive and scream “this guy knows what he’s doing.”

The Best Men’s Wingtip Boots At a Glance

BEst Men’s Wingtip Boot

Allen Edmonds Dalton Wingtip Dress Boots

Buy at Nordstrom $475 Jump to Details
Most Interesting

Taft Saint Boots

Buy Now On Amazon $350.00 Jump to Details
Best Fitting

Beckett Simonon Nolan Brogue Boots

Buy at BEckett SImonon $259 Jump to Details
Best Everyday Boot

Thursday Boots Wingtip Boots

Buy at Thursday Boot Co. $235 Jump to Details
Best Mixed Media

Taft Livingston Wingtip Oxford Boot

Buy Now On Amazon $295.00 Jump to Details
Best Splurge

Thom Browne Classic Wingtip Lace-Up Boots

Buy at Saks Fifth Avenue $830 Jump to Details
BEst Color Wingtip Boot

Bruno Magli Gleason Lace-Up Wingtip Boots

Buy at Bruno Magli $299.95 Jump to Details
Courtesy of Thursday Boot Co.
Courtesy of Nordstrom
BEst Men’s Wingtip Boot

Known for making some of the most comfortable dress shoes, the Allen Edmonds brand exudes class, function, and quality. Those are three defining pillars of the best boots for men, and that’s exactly what’s found in the Dalton Wingtip Dress Boots. Made with European leather in Port Washington, Wisconsin, the Dalton boot is ornately crafted with fine broguing on the wingtip itself and along the stitching throughout.

With heavy “Peaky Blinders” vibes, this is exactly the shape and style of a men’s wingtip boot that should be worn with a tailored suit as one strides through the streets of old Birmingham in the modern era. But truthfully, this boot is versatile enough to wear with anything.

Aside from premium quality, Allen Edmonds is also known for their wide range of sizes and shoe widths. The Dalton is available in sizes ranging from men’s US 5-16 and offers 10 different widths. For the best wingtip boots with the best fit possible, look no further.

Courtesy of DSW
Most Interesting

Coolest Feature: Taft is well-known for making some of the coolest-looking shoes today and their Saint Boot follows suit with its Bottega Vanetta-style basket weave.

ROI: Like Thursday Boot Co. and Beckett Simonon, Taft is another brand offering more awesome for less money. Taft products go the distance for years of wear.

Hot Take: This men’s wingtip boot is just so f##king cool it’s hard not to fall in love with them immediately. The basket weave style is not commonly found in this type of boot, let alone boots at all, which makes them infinitely more special.

Available in black and espresso up to a size 15, this boot is made with a full leather upper, a leather insole, and a leather outsole with rubber for traction. The Blake stitch adds a very refined edge to polish off the boot and allows it to be resoled in the future after wearing them all the time.

Courtesy of Beckett Simonon
Best Fitting

$259 $400 35% off

Buy at BEckett SImonon

Coolest Feature: Built on the same last as their popular Dowler Boot, this style is generous in the toe box for unbeatable out-of-the-box comfort.

ROI: While fine leather and handcrafted detailing can jack the price up on a nice boot, Beckett Simonon’s made-to-order business model cuts out the middleman, passing the savings on to the consumer. For the quality materials and craftsmanship here, it’s hard to find a better deal. The only downside is having to wait a month or two to receive them.

Hot Take: If comfort, quality, and fair pricing weren’t enough, then revel in the fact that Beckett Simonon also sources its leather for these boots (and all other products) from an Italian tannery awarded with a Gold Rating by The Leatherworking Group in efforts to bring ethical balance to the force of leather manufacturing.

For the wine lovers in the back, the Nolan Brogue Boot is one of the only year-round styles found in a color other than whiskey brown and licorice black — the brand’s distinct Bordeaux red. In person, it’s a deep bloody shade of handsome and is widely coveted by friends.

Read More: My Friends Keep Buying These Boots After Seeing Me Wear Them

Courtesy of Thursday Boot Co.
Best Everyday Boot

Coolest Feature: The Men’s Wingtip Boot from Thursday Boot Co. advocates for personal style with seven different colors to choose from in this one particular style. That’s insane.

ROI: With every pair of Thursday Boots SPY has tried, it seems they’re continuously slinging great quality boots for an equally as great price. Feel good about shopping here.

Hot Take: Thursday Boot Co. has taken a firm grip on the boot market with their handsome, easy-to-wear styles aplenty from plain-toe boots to cowboy boots and every style in between. This wingtip boot, like the rest from their collection, is built on studded rubber outsoles to compliment the brand’s sleek silhouettes.

While this boot toes the line between classic and modern, one certainty is that they’re even more versatile than MLB sensation, Shohei Ohtani. To rock these harder than Ohtani has rocked baseball, opt for some dark stretch denim and one of the best men’s t-shirts.

Read More: Thursday Boots Released a New Matte Black Combat Boot, The Titan, and It’s Sick

Courtesy of Nordstrom
Best Mixed Media

Coolest Feature: The Taft Livingston is the “Gangsta’s Paradise” of wingtip boots — immediately recognizable. Of course, this only works if the gangsta is Sherlock Holmes.

ROI: Taft is rising like Microsoft in the ’90s right now as they churn out styles that make guys drool. With the Livingston boot, not only is it a timeless style anybody would be happy to wear into 2030, but the lug sole will ensure they get there, boosting the sole’s longevity.

Hot Take: For anybody online window shopping through men’s wingtip boots, styles seem to blend together after the first hour. Most styles, while sexy, are plain. One thing that sets Taft apart as a brand is not being afraid to try stuff, and the Livingston Wingtip Oxford Boot is a prime example.

A boot with mixed media? Yes, please. This wingtip boot stands out like a very not sore thumb. It’s a compliment machine, as onlookers glare in confusion and then in immediate awe, asking, “where can I get a pair of those?”

The Glen plaid upper pairs beautifully with dark brown leather accents. The secret? A little splash of Burgundy. The red ties everything together on top of a Blake-stitched lug sole.

Courtesy of Nordstrom
Best Splurge

Coolest Feature: If coming from the mind of Thom Brown isn’t cool enough, this wingtip boot boasts a textured calfskin leather that catches light at different angles that makes them shine both literally and metaphorically.

ROI: North of $800, this is splurge purchase territory. Budgets aside, the boots’ premium Italian leather and craftsmanship are synonymous with quality goods. And the full rubber sole will only extend its life.

Hot Take: From the king of tailored style and the man who changed how guys wear suits (slimmer, shorter, cooler) comes a pair of luxurious wingtip boots fit for the man ready to add to his designer shoe collection. Alongside the textures calfskin leather is the Thom Browne signature tri-color pull tab featured on all his shoe styles. In black, this boot could be an everyday staple underneath an iconic Thom Brown 4-Bar Blazer and matching trousers.

Courtesy of Bloomingdale’s
BEst Color Wingtip Boot

Coolest Feature: The brushed olive suede of this wingtip boot from Bruno Magli pops hard with any neutral-based outfit.

ROI: Bruno Magli boots, along with their shoes, are known for comfort and longevity. With quality materials combined with a cushy crepe sole, These boots will last for years if properly rotated.

Hot Take: Playing true to the spirit of men’s wingtip boots, adding a pop of color can be the difference maker between getting noticed and being able to Irish exit. Opting for a bold statement instead of a classic leather color is a nice way to round out a boot collection. The olive suede is vivid in both the dead grey of winter or a sea of basic bros in their Allbirds and Patagonia vests.

Can You Buy Men’s Wingtip Boots Second Hand?

If a pair of wingtip boots is laying around a Buffalo Exchange, snag them. Because the style isn’t as widely offered brand new, that means the aftermarket for the best wingtip boots is even more limited.

Styles like the Allen Edmonds Dalton Wingtip Boot show up more frequently than others because its a continuative model, meaning it’s sold year-round. These hold their value well, averaging between $90 and $200 for a used pair on Ebay.

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