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A Man’s Guide to Wingtip Dress Shoes

A Man’s Guide to Wingtip Dress Shoes


Full Brogue.

One in the same?

What’s the difference between that and a quarter brogue, long-wing brogue, and a semi-brogue?

When can you wear wingtips, and with what?

Answering all those questions is what this article is about!

The wingtip shoe is instantly recognizable, but its function and the details of its form have changed over the years, from its peasant origins to 21st century updates and interpretations from some of the top shoe houses in the world.

What Is a Wingtip?

In broadest terms, a wingtip is any shoe in which the toecap is extended with low “wings” that reach around the side of the shoe.

Get much more specific than that, however, and you start encountering exceptions.

Most wingtips – but not all – are brogued, meaning they have decorative perforations along the edges of the toecap, and often in other places as well.

Many wingtips – but not all – extend the wings all the way around to meet at the back of the shoe, creating a low band of leather that circles the shoe where the upper meets the sole.

And some wingtips, but certainly not all, opt for a “two-tone” color scheme wherein the body of the shoe is one color and the toecap with its wings another.

So there are many varieties, but they all share one defining feature: an extended toecap with wings that reach around the sides of the foot.

Where Does the Wingtip Style Come From?

Paul Evans Wingtip BroguesWingtips are part of the brogue family. Traditionalists and people who want to sound smarter than you will still insist on calling them “full brogues.”

That’s not wholly accurate, since shoes with wingtipped caps but no broguing have been around for centuries, but take it as a polite nod to history: the “wingtips” that entered mainstream British style, and from there American style as well, back in the early 20th century, were descended from the Irish and Scottish walking shoes known as brogues.

Brogues were heavy shoes of thick leather with holes punched all the way through, to allow water to enter and then flow back out when the wearer was crossing boggy country.

That may sound unpleasant to modern ears, but in a world without waterproof coatings and machine stitching, walking inevitably meant wet feet, and brogues at least allowed them to dry faster.

Fashionable shoemakers eventually got hold of the style, and a whole family of shoes with decorative hole punching on the surface (but not all the way through the leather) evolved.

The wingtip, or full brogue, was the most decorated and least formal member of the family:

Dress shoe Guide Brogues wide 1

  • Quarter brogues have a toecap seam lined with decorative perforations, but no other brogueing.
  • Semi-brogues have brogueing along the toecap seam, and also on the top of the toecap leather, but not anywhere further up the shoe than the toecap.
  • Full brogues extend the toecap with wingtips, and have brogueing both on top of the toecap and along the seams, and often on the body of the “wings” as well.
  • Longwing brogues is a term sometimes used to set apart wingtips where the wings meet at the back of the shoe, forming a complete circuit of the shoe. They are a subset of the wingtip style.

Any or all of these can also sometimes (but not necessarily) feature decorative edging or serrations along the seams, particularly the toecap seam.

Paul Evans Wingtip Brogues

How Formal or Casual Are Wingtip Dress Shoes?

Wingtips are a historically casual style, particularly the two-tone “spectator shoe” variety wherein the uppers and the toecap are contrasting colors.

These were historically leisure shoes, and the visually “busy” style means that in today’s fashion language they’re still more casual than a sleeker, non-perforated Oxford or other dress shoe.

That said, they’re not sneakers, either. Wingtips are smack in the middle of casual dress shoes (or dress-casual shoes, if you prefer).

You shouldn’t wear them in serious and high-formality business settings, or to somber affairs like funerals, but other than that they’re fair game for wearing with suits, slacks and sportcoats, or even just jeans and a casual collared shirt.

A lot will depend on the color and design of the shoe. A black wingtip with narrow wings that stop midway around the foot and a single line of small perforations is relatively dressy; a two-tone shoe with white uppers and oxblood wings that go all the way around the foot is much more casual.

In general, the more holes the shoe has and the bigger the wings, the less formal it is. But color can play a part too – black will always be a bit dressier than brown, and other colors like red and white will always be on the low end of formality.

Should I Buy a Pair of Wingtips?


If you’re looking for your first pair of really good dress shoes, the answer here is no – a wingtip shoe style is not where you want to be starting.

It’s a striking look, and it can be a great one with the right outfit, but it’s not as versatile as a pair of simple Oxfords. You should not be using wingtips as your go-to shoe for every occasion that demands leather dress shoes.

If, however, you’ve got a more staid pair or two for dressy occasions, a pair of wingtips can be a nice step in expanding your dress-casual options. They add a nicely relaxed and fun-loving air to a social/leisure outfit.

Think of them as shoes that say “off the clock, but I still care about how I look.” (They might be worn on the clock too, of course, particularly in relaxed but well-heeled sectors like the tech industry, but for most people’s purposes wingtips should be social clothing first, and business clothing distant second or not at all.)

The Wingtip In Conclusion

Modern interpretations have given you a lot of options to choose from if you go the wingtip route, ranging from scaled-down versions that flirt with business formality to truly exotic, neon-colored two-tone showpieces.

Find one – or two, or several – that fit your wardrobe and your personality, and go to.

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