A Beginner's Guide To Men's Wingtip Shoes (2024 edition) (2024)

Whether you're dressing for work, a date, or just a weekend trip with the kids – men's wingtip shoes are a great option to help elevate your style without looking too formal.

But as with any item of clothing, you can't expect to look a million bucks if you just throw on a pair without knowing the style basics. There are rules you need to follow and key facts you need to know.

Don't sweat it; that's what I'm here for. Today I'm breaking out everything you need to know about wearing, styling, and looking fantastic in men's wingtip shoes.

By the end of this article, you'll discover:

1. What Is A Wingtip Shoe?
2. Wingtip Shoes History
3. Wingtip Shoe Formality
4. Who Should Wear Wingtip Shoes?

#1. What Is A Wingtip Shoe?

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

However, when you start to get into the technical details of this footwear style, you begin 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 is another.

What I'm trying to say, gents is that there are many varieties – but they all share one defining feature: an extended toecap with wings that reach around the sides of the foot.

#2. Wingtip Shoe History

Wingtips are part of the brogue family. Traditionalists will still insist on calling them “full brogues.”

However, that's inaccurate since shoes with wing-tipped caps and no broguing have been around for centuries. It's best to take this technicality with a pinch of salt and recognize that it's a polite nod to history.

The “wingtips” that entered mainstream style back in the early 20th century were descended from the Irish and Scottish walking shoes known as brogues.

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

Gross, right? To us, it might seem so, but in a world without waterproof coatings and machine stitching, walking outside often meant wet feet and brogues at least allowed them to dry faster!

Fashionable shoemakers eventually adopted the style, and a whole family of shoes with decorative holes on the surface was born.

#3. How Formal Is A Wing Tip Shoe?

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

The visually “busy” style means that they're still more casual than a non-perforated Oxford in today's fashion.

That being said, they're not sneakers, either. Wingtips are somewhere in the middle as a casual variant of formal dress shoes (or dress-casual shoes, if you prefer).

You shouldn't wear them in serious and high-formality business settings or too somber affairs like funerals. Instead, wear them with sports coats and slacks or just jeans and a casual collared shirt.

It's essential to be mindful of the color and design of the wingtip shoe:

• An all-black leather wingtip with narrow wings and a single line of small perforations is relatively formal.
• A two-tone shoe with white uppers and oxblood wings that go all the way around the foot is much more casual.
• Suede wingtip shoes are the least formal and should not be worn with a suit. However, they're great for casual summer outfits.

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. As with any shoe, black will always be dressier than brown.

The wingtip, or full brogue, is the most decorated member of the brogue family:

• Quarter brogues have a toe cap seam lined with decorative perforations but no other brogueing.
• Semi-brogues have brogueing along the toe cap 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.
• 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.

#4. Who Should Wear Wingtip Shoes?

If you're looking for your first pair of perfect dress shoes, avoid men's wingtip shoes.

It's a striking look and can be great with the right outfit. However, they're not as versatile as a pair of simple Oxfords for formal clothing.

You should not be using wingtips as your go-to shoe for every occasion that demands leather dress shoes.

However, if you already own a pair of formal dress shoes, a pair of men's wingtip shoes can be an excellent step in expanding your dress-casual options. They add a relaxed and fun-loving air to most social/leisure outfits.

Think of them as shoes that say, “Hey, I'm off the clock, but I still care about how I look.”

Modern variations of the wingtip have broadened the formality of this footwear style. There is a wingtip shoe for everyone, ranging from scaled-down formal versions to neon-colored two-tone showpieces.

Learning about wingtips is only the start. Click here to discover the other essential shoes a man must have in his closet.

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