Style Q&A: What’s the Deal with Wingtips?

The infamous dress shoe explained.

Please help out a confused teenager who enjoys reading Primer Magazine. What are Wingtip shoes and why are these shoes better and more expensive than regular dress shoes? – Jonathan

We’re glad to hear that as a young man you’ve chosen to focus on your footwear.  Many men, young and old, focus too much on building their wardrobe from the top down instead of the bottom up.  A proper wardrobe isn’t proper without proper footwear.  Forgive the repetition.

That being said, wingtips are only one of the many options a man should have in his footwear collection.  Contrary to popular belief among style novices, wingtips are actually more casual than they are formal, they shouldn’t be the first selection for a beginning dresser, and they don’t cost as much as other types of quality footwear in general.

In order to understand the value of wingtips one must understand their history.  “Wingtips” as they are most commonly referred to are actual a type of brogue.  Brogues were shoes originally worn in the Scottish Highlands which had holes or perforations punched into the leather in order to allow water to pass through the shoe without soaking into it. It is this brouging from which wingtips are formed.  The wingtip is named this way for its resemblance to the wings of a bird.

The traditional wingtip is slightly less formal than a plain and/or perforated cap toe shoe.  Its brouging produces a bulkier and less sleek appearance because it requires more than one piece of leather to be attached to another.

In the world of high quality footwear, “less is more” applies to decoration and the amount of leather used.  The more ornamentation and the more leather used to create a shoe the less formal it is.  Wingtips can use up to 3-4 different pieces of leather which means there is more chance for the leather to be imperfect as opposed to  whole cut shoe which only uses one single piece of leather which needs to be flawless since imperfections in the leather cannot be hidden.

There are several different types of brogues to choose from including semi, quarter, full (wingtip), or long.  Quarter brogues only have brouging on the toe and shoe waist.  Half brogues extend from the toe halfway back to the waist. Wingtips and long wings extend all the way around to the heel.

As you can imagine after our description of brouging, the longer the wingtip, the more casual it is.  By causal we do not mean that wingtips should be worn with shorts or that they are in the same category with sneakers.  We mean that in the category of dress shoes which are inherently more formal than casual shoes, wingtips fall in the middle of the pack when it comes to formality.

At the end of the day wingtips certainly should hold a place in the wardrobe of any well-dressed man.  It just shouldn’t be the first place.

style qa

Grant Harris is Owner & Chief Style Consultant at Image Granted; a Washington, DC based Image Consulting Company dedicated to solving the complex image, style & fashion issues of today's professional man. He has a healthy obsession with socks. Follow him on Twitter & Facebook.

  • Danno

    Thanks so much! I had wondered the same thing about wingtips. Solid article. Could you write one about the history and different styles of oxfords?

  • Bolo Yolo

    Great article. I like how you state that man should build his wardrobe from the bottom up. I heartily agree. My personal style is casual sporty.
    I believe in 3 styles for mans: casual leisure, casual dressy, and casual sporty. And it all start with the shoe. In fact, for me, it’s all about the shoe. I like comfortable casual shoes.

  • Jonathan

    Thank you so much for answering my question. Your article was a great insight into wingtips.

  • The Modest Man

    Nice overview of wingtips. Need to pick some of these up. I like those Rockports…

  • Christopher

    Those are all beautiful shoes and all in an amazing color. Good work there. I recently picked up a great pair from Too Boot New York and they look stunning.

    I did a really nice review of the company and the thought process behind buying good shoes on our site if anyone’s interested.

    But these are all great brands too. I’m partial to the Edmonds… as everyone is i’m sure. Edmonds is probably the most popular name in mens shoes at the moment. At least from the crowds I talk to about dress shoes.

    Great article Grant. Thanks for the work and the nice pictures.

  • Mark

    I just bought my first pair of nice dress shoes (allen edmonds strands).. I was planning on making these my primary brown dress shoe since my couple other pairs are junkers that I plan on recycling soon. Are you saying that I should have gone instead with a more classic shoe with less decoration and then move into brouging???

  • Grant

    @Danno – Glad you enjoyed it. I’ll discuss with Andrew and see what we can do.

    @Bolo – Interesting take on your catgories of style. Sounds like you have no use for business and/or formal wear. The life of leisure is a good life.

    @Johnthan – My pleasure, thanks for asking!

    @Christopher – I’ve seen Too Boot on several ocassions. There is one model I like in particular. It’s a suede split toe but the stitching is just a bit off and is unpleasing to the eye…at least mine anyway. I’d like to see your review. Please share.

    @Mark- Fr your first pair of good shoes you couldn’t have made a better choice when it comes to the brand. You’ve done well to take Andrew’s advice. However, I would’ve eased you into something more sleek and less busy for your first shoe. A plain toe, cap toe, or even split toe would’ve have been enough. These options are more versatile and less busy. However, you’ve made a great choice for the long haul. Now its just a matter of adding more quality pieces. Good luck on your journey.

  • Chris

    Thoughts on black wingtips? Are they sort of an oxymoron? (black being “formal” and wingtips inherently “casual”)

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  • Chris Jones

    Huh, you don’t often see wingtips without broguing… looks good.

  • Brandon

    Great Job. I am looking to buy my first pair of wingtips.

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  • Confused

    Explain why some Wingtips are normal foot length and others look like elf shoes or the shoes the Penguin wears in Gotham.They extend about 2 inches past the large toe. How do I know which are normal when ordering?

    • Andrew

      That’s a great observation. Generally you can tell by the length of the toe box, how much of a point the shoe comes to, or how much curve there is to the front of shoe. These things all suggest more clown shoes.

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  • Laura Salovitch

    I’ve always considered wingtips to be ‘business’ shoes (worn with a suit and tie). Have I been mistaken?

    • Andrew

      They are today considered dressy, but were originally sporting shoes. Menswear aficionados still consider them more casual than dressier alternatives, but most men do not know the distinction.

      • Red Dog

        Or care.