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Deep Dive: All About the Wingtip Shoe

Four pairs of wingtip shoes

Wingtip shoes are a classic look in menswear. They are characterized by a leather overlay on the toe that makes a W shape (or a wing shape). Over the years they have been a popular style of shoe, but they’ve got a long and convoluted history.

Depending on who you ask, the definition of a wingtip shoe might vary. We like to keep things simple, so we consider anything with the W shape on the toe a wingtip. We’ll dive into that more in a second.

Wingtip shoes are a statement on their own, usually indicating a certain level of style and knowledge about fashion. After all, wingtip shoes are not usually the first pair of dress shoes a guy buys.

We decided to dig into their roots and give some tips on how they should be worn.

What the heck is a wingtip shoe

Brogue shoe vs. wingtip shoe

Four wingtip shoes in a circle

This can get a little confusing.

Wingtip shoes are often referred to as brogues because a “full brogue” shoe incorporates a perforated wingtip shape on the toe. However, calling all wingtips “brogues” is not always technically accurate.

“Brogueing” refers to the perforated detailing on shoes. Sometimes those details are just on the toe, and sometimes they’re around the whole shoe. A brogue shoe does not always incorporate that wing shape.

Further, not all shoes with the wing shape are perforated. If there is no brogueing, the wingtip shoe is technically called an “austerity brogue.” We think it’s a bit confusing to call a shoe with no brogueing a “brogue shoe,” so we just call it a wingtip.

In essence, sometimes wingtip shoes have brogue detailing, and sometimes they don’t. Sometimes brogue shoes have a wingtip design, and sometimes they don’t. They are not always one in the same.

We think it makes the most sense to call any shoe with the wing shape a wingtip. Clear? Clear.

The origin of the brogue

Brogue wingtip shoes from the side

Brogue shoes date back to the 16th-17th century, originating from the Galeic word “brog,” which literally means “shoe.”

The perforations were added to thick, leather shoes in Scotland and Ireland to allow water to pass through as they were wading through boggy terrain. It was not acceptable to wear them anywhere other than in the countryside.

As is the case with many fashion trends, eventually the city folk caught on, and brogueing became an aesthetic choice rather than a functional one. What once was strictly a work shoe became a fashion statement.

The origin of the wing shape itself isn’t well known, but it’s assumed that the original function was as a reinforced toe cap which was stylized a little later on.

The Prince of Wales was seen sporting full brogues during a golf trip in the early 1900s, solidifying their place in the men’s fashion world. Later, we’d see other major cultural icons wearing the style, like Elvis Presley.

Today, they have their place on many men’s shoe racks, functioning as a crossover between dressy and casual footwear.

Tips on wearing wingtip shoes

While we don’t suggest that a wingtip shoe should be your very first pair of dress shoes, it is an excellent addition to any man’s wardrobe.

It’s not a formal shoe

Because a wingtip requires the overlay of leather to make the wing shape, it’s bulkier than most other types of shoes. This by default makes it a more casual shoe than many other leather shoes.

In fact, the more ornamentation a shoe has on it, the less formal it typically is. A full brogue--which has the wingtip design as well as brogueing details across the entire shoe--is the most casual of the bunch. Avoid wearing them to formal events or galas.

But they’re not strictly casual either

Just because the wingtip isn’t a formal shoe doesn’t mean it can’t be dressed up. We love it as a date night shoe or even as a wedding shoe for a guest. It can also be worn quite casually, making it particularly versatile.

Consider the colour

Light coloured brogue shoe

As is the case for most attire, a lighter coloured shoe is more casual, and darker is dressier. A dark brown or black wingtip shoe can easily be worn with most business suits. A lighter brown leather or suede wingtip looks extra slick with jeans or chinos.

Avoid wingtip shoes with different colours of leather unless you really want your footwear to be the main attraction.  

Balance the weight

The chunkiness of the wingtip shoe is crucial to how dressy or casual it is. An English pair is usually bulkier, and Italian wingtips are usually a bit more sleek. Make sure the weight of your trousers is evenly matched. In most cases, a super skinny jean isn’t ideal, nor is a dress pant on the tighter side. Aim for a relaxed trouser, and make sure the hem sits right at the top of the shoe.

Where to wear wingtip shoes:

  • At the office
  • Dinner dates
  • Business lunches
  • Job interviews
  • As a wedding guest
  • Market strolls
  • European vacations
  • Cocktail events

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So there you have it. What started as a purely functional shoe for wading through the bogs of Scotland and Ireland has evolved into the stylish, multi-purpose, footwear we have today. Check out our selection of wingtips and other footwear here. 


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