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Wingtip Shoes: From Bogs To The Boardroom

The featured image is the Flair Wingtip Oxford in Navy.

The wingtip. It is a style every man should own. The wingtip shoe is a classic that never goes out of style. First worn in the rain-drenched Scottish Highlands in the 16th century, the perforations in the original wingtips were punched into the leather so water could pass through without soaking the shoe and allow it to dry out faster. Because of this rustic origin, wingtip shoes were considered a country, outdoor shoe.

The wingtip, of course, got its name as the perforations along the toe resemble the wing of a bird, thus wing tip. These holes are known as broguing. The name comes from the Gaelic word bróg, meaning shoe, and in the 1900s the word was used for any footwear you’d wear for a muddy ramble. Today the word is used to denote the holes punched in the toes, though it is often used to mean any shoe with detailing. Although most wingtip men’s shoes are formed by this broguing there are also wingtips created without broguing. A smooth toe cap that has that swoop of leather toward the heel resembling a wing are also wingtip oxfords.

Today there are numerous versions of the men's wingtip shoes. The long wingtip has perforations running from toe to heel while the short wingtip has perforations ending about halfway along the side of the shoe. Popular men’s wingtip shoes run from dress versions made in premium burnished leather, to men’s wingtip boots, and even hybrid sneakers with suede or textile designs and athletic soles.

It is this evolution of the style that makes it such a versatile addition to any wardrobe. Although they are not appropriate for the most formal occasions, wingtip dress shoes can be worn with everything from your best suit to your favorite jeans. And the more informal style of men’s wingtips like a colorful hybrid version with a contrasting wedge sole offer the versatility to wear to the office, a night out or weekend barbeque. 400 years ago, when a clever Highlander punched a series of holes is his shoes to keep his feet dry, little did he know that his new “wing tip” would endure and become one of the most versatile and beloved styles of the day.

Here are a few of our go-to wingtip styles for men:

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