A lesser-known style of brogue shoe, longwings are very similar save for the toe ornamentation that wraps around the entire shoe. Longwing shoes are of particular interest to shoe enthusiasts as an intriguing and rustic alternative to more common styles.

This guide will provide you with a detailed overview of longwing shoes including:

You can scroll down to read the guide in its entirety or use the links above to jump ahead!

Perspective View Of Longwing

What Are The Best Longwing Shoes For Men?

In this section of the guide, we explore our top-rated longwing shoes. You can use the menu below to easily jump between the entries. Otherwise, scroll down to discover them all.

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1. Johnston & Murphy Conard [Best Value]

Johnston & Murphy Conard Wingtip Longwing
  • Color: Black, Mahogany
  • Material: Calfskin Leather
  • Pricing: $170 [Buy From Zappos]
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Crafted from calfskin leather, the Johnston & Murphy Conard wingtips offer excellent value for money. The high-quality broguing is subtle yet elegant and leaves a detailed finish and ornamentation for the shoe.

2. Bostonian No. 16 Longwing [Premium]

Bostonian No. 16 Longwing
  • Colors: Burgundy, Black
  • Material: Leather
  • Pricing: $480 [Buy From Zappos]
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Made in the USA, the Bostonian No. 16 Rhodes is a more premium Longwing option. Made from American tanned leather, they’re constructed using a Goodyear leather welt.

3. J&M Collection Reece [Wholecut Longwing]

J&M Collection Reece Wing Tip Wholecut Shoe
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From the brand’s J&M collection, the Reece is a little different compared to the other longwings in this list. The shoe itself is has a wholecut design while the longwing ornamentation is achieved through perforations across the uppers. If you’re looking for an original longwing, this is an excellent choice.

4. Magnanni Vandar [Most Stylish]

Magnanni Vandar Longwing Shoe
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Another unique-looking shoe, the Magnanni Vandar is a Spanish-made longwing. With a design inspired by continental style, it’s much more streamlined and somewhat dressier than the traditional longwing shoes in this list.

5. Florsheim Kenmoor Wingtip [Goodyear Welt]

Florsheim Kenmoor Longwing Brogue
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Available in smooth black or cognac pebbled leather, Florsheim’s Kenmoor is somewhat more premium than their usual offerings. Both versions are made from calfskin leather and are constructed using a Goodyear welt.

6. Dockers Hausman [Most Affordable]

Dockers Hausman Longwing Shoe
  • Colors: Butterscotch, Dark Tan
  • Material: Full-Grain Leather
  • Pricing: $90 [Buy From Zappos]
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An affordable longwing shoe, the Dockers Hausman comes in a variety of styles and materials. You can opt for a classic burnished tan leather. Alternatively, there are other options that combine different materials such as brown full-grain and tan suede.

What Are Longwing Shoes?

Top And Side View Of Brown LongwingA longwing is a style of brogue in which the wingtip perforations span the full length of both sides of the shoe, meeting at the heel counter. In other words, the “wing” tip is “long”er than your typical brogue, hence the term “longwing.”

“Longwing” is therefore not a structural element like oxford or derby, but rather an aesthetic one, such as brogue, bit, or bicycle toe.

It is worth nothing that more often than not, they are made in the derby style with open-throat lacing systems as opposed to the closed-throat oxford style. The detail can also show up on loafers, monkstraps, and other styles of shoe.

Available in nearly every color and material under the sun, longwings are a shoe style that can work with just about anything. Whether ready-to-wear or custom made, it’s good to have a pair in your closet.

Two Side Views Of Brown Longwing

History Of Longwings

Crimson Longwings Showing SoleLongwings’ history is tied up in that of the brogue: coming into existence centuries ago in Ireland and Scotland, brogues were shoes made for wading in water; the perforations were actual holes that would allow liquid to drain from the shoe when exiting a body of water.

The longwing hit its stride in the 1970’s, especially with the brands Florsheim and Alden. In the United States especially, it’s commonly worn as a business professional shoe with suits and ties. While this belies the wingtip’s heritage as a country shoe, there are versions that have the slim proportions of a dress oxford that pair nicely with suiting.

It’s also common to see longwings with chunky, casual proportions like double leather soles with wide welts, rounded toe shapes, and large heels.

Today, the shoe retains its popularity across various reputable men’s shoe makers.

Go Long(wing): How To Wear These

Though they’re all brogues, not all longwings are created equal. Some are dressier than others, meaning that there are some that will pair beautifully with jeans and casual trousers, while there are others that are great with suits.

Collage Of Brown Longwings With Jeans

It seems like rudimentary advice, but it’s worth repeating: use your best judgement when getting dressed. Your gut will know, learn to trust it.


Longwings occupy the same general space on the formality scale as full brogues as they are simply a different version of a full brogue. Like brogues, their proportions can either be slim or chunky, and you should adjust your attire to sync with this as needed. Some suggestions are as follows:

  • Jeans and casual trousers: Chunky longwings in suede or calfskin
  • Country suits (flannels, tweeds, etc.): Chunky longwings with rubber sole, preferably Dainite
  • Worsted wool suits: Slim longwings in calfskin or cordovan


Because longwings are made in every color from bone to black and in a wide selection of materials ranging from suede to nubuck and calfskin to cordovan, you can find a pair to fit an outfit twelve months out of the year.

Below, we offer some suggestions as to materials and colors by season. This list is not exhaustive, though, and we’d love to hear about anything else you’ve tried in the comments!

  • Spring: Any shade of lighter brown leather or suede: tan, oatmeal, British tan, caramel, nutmeg, etc.
  • Summer: White and off-white suede or leather (a longwing white buck is a great addition to a summer wardrobe)
  • Autumn: Crimson or tobacco-colored leather
  • Winter: Black, chocolate, and burgundy leather or cordovan

Longwings: Purchase Or No?

If you’re a guy who lives on a steady diet of jeans and button-downs or sweaters, we can’t recommend a chunky longwing enough. The proportions sync beautifully with casual clothing, and the pinking and perforations of the shoe add a lot of visual interest to such outfits If you tend to dress up a bit more, look into a pair that’s a bit more sleek and streamlined.

Either way, a longwing is a good fifth or sixth shoe to add to a collection.

What Next?

Now that you have learned about longwing shoes, check out some our related footwear guides for men:

Men's Longwing Shoe Guide
Reviewed by Michael D., on .
"Really helpful, thank you. I stumbled upon some longwings by accident but wasn't sure how you'd wear them. Thanks for this guide, I've picked up one of your recommendations."
Rating: 5.0 ★★★★★

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