Wingtips – They’re regularly featured as some of the best and most essential dress shoes for men. You’ll see them on guys wearing jeans on their day off, and then spot a pair gracing prince William’s feet on what is supposed to be a formal occasion.

Wingtips are visually more detailed than the typical dress shoe and usually receives much more compliments from women and, occasionally, other men. There are many types of wingtip shoes and these subtle differences makes it easier to personalize the right type to your style.

Wingtips and Their Close Cousins

Along with wingtips, three other shoe types make up the brogue family, bringing the total to five if you count two-toned spectators. The chief difference between all of them lies in the amount of broguing or perforations which adorn the heel cap and other parts of the shoe. The subtle, more subdued quarter brogues can pass as being business dress-worthy, especially if they’re black, while models which sport more holes steadily become more casual.

  • Longwings are the most developed of them all in terms of broguing. They sport a wingtip, and the wings span all the way from the toe cap to the heel, decorating it and making a heel cap unnecessary.
  • Wingtip shoes or full brogues are the most widespread and instantly recognizable because of the point that reaches out towards the laces, creating a “tip” on the vamp where the two wings which extend towards the shoe’s sides meet. Broguing is usually also present on the sides of the laces and along their seams.
  • Half brogues don’t have wingtips. Rather, their broguing outlines the toecap without reaching for the sides, and the cap itself has less perforations.
  • Quarter brogues’ main connection to wingtip shoes is the lightly brogued toecap. Usually just the strip that outlines it has holes while the rest of the shoe isn’t brogued at all.

Origins of the Wingtip Shoe

While today wingtips are that kind of shoe you’d dread to get even a speck of dirt on, the complete opposite was true for their ancestors. The first mention of brógs, simply translated from Irish as shoes, comes from the 1500s. Back then, they were made using two pieces of untanned leather and used almost exclusively as a countryside shoe throughout Ireland and Scotland. The perforations on these practical brogues were themselves there for necessity – a hunter going after birds and game or a soldier on the march would often have to do so while traversing swampy and wet ground. Since the shoes weren’t treated in any way they’d quickly have rotted away if water was left in them, so the holes helped a lot in getting them dry quickly.

Making brogues by hand was tedious work, and even though the process was made easier by the 1700s, they retained their original, limited use. Mass production saw them revitalized at the start of the 20th century, with VIP-s like the duke of Windsor making the two-toned variant a popular sight at sporting events, which is why they’re sometimes also called “spectators”. The public caught on when the likes of Fred Astaire started showing them off, and the phenomenon jumped the pond after WWII when returning American soldiers brought some home with them.

Wearing Wingtips Properly

Guys are often confused when figuring out when wearing wingtips is considered appropriate. This isn’t surprising since their appearance is a healthy mix of a gentlemanly, sophisticated leather build akin to more formal footwear and nostalgic decorations that bring you back to the dance halls of the 30s and 40s.

The fact remains though that the wingtip is a dress shoe in the casual sense. If you’re giving a presentation in front of a group of investors, you’ll want to wear something that fits the clean-cut, strong-lined world of business more like whole cut or cap toed oxfords. Then again, if casual Fridays or business-casual is the norm, wingtips won’t make you feel underdressed.

When it’s time to unwind over the weekend or step out on the town, that’s when wingtips really shine. A jazz club, your friend’s housewarming party and a lazy Sunday morning spent on the terrace of your favorite café are the wingtips’ natural environments. Pair them with a blazer or sports jacket in a dark tone such as navy blue or grey, and a pair of linen slacks, flannels, or dark blue jeans to make the look complete.

The wingtips’ material and color play a part in how formal they are too. Shiny boxcalf leather is the material of choice, but different, more casual options like suede are also fetching. More conservative colors include unavoidable black and dark brown, with oxblood and lighter shades of brown being equally popular.

Finally, two-toned wingtips or spectators can’t be pulled off by just anyone and are seen as the most extravagant of the bunch, especially if their colors are in stark contrast. True to their name, they’re best worn when spectating at an upscale sporting event such as a horse race, tennis match or golf tournament. Brighter tones work best with spectators – a pair of white or tan slacks and a light blue shirt topped off with a smart sports jacket bring out the best in them.

With the many options and styles of wingtip shoes to choose from, be sure to check out our review of the top men’s wingtip shoes.

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