We often discuss the most timeless pieces of menswear. Is it the double-breasted suit? A piece that came to life in the 1930’s inspired by the naval reefer jacket and has returned to prominence seems like the obvious choice, and maybe it is. However, style starts from the ground-up, and so today I’m going to address the wingtip. Falling under the larger category of Brogue shoes, it is characterized by its multi-piece, leather uppers which start at the cap-toe of the shoe and fan around like a widows peak hair line back around to the side of the shoe. Resembling almost a “W” at the toe, the wingtip traces origins back to Ireland or Scotland.
This historic piece of menswear has lasted the test of time, and become such a staple in modern design that we now find variations of it applicable to every sartorial situation and every dressing dilemma. Today I will explore 3 vastly different types of wingtips, and I how sport ‘em all uniquely.
Saturday Swag, Saturnight Sharp
This pair of Generic Surplus Leather Wingtip Sneakers has been in my arsenal for about 2 years, and while this pair begins to fade, I just ordered a new pair in black. These shoes deserved the re-order for one reason only, versatility. Pair em with Jeans like these Levi’s 511’s, a white T-Shirt, Shawl Collar Cardigan, and a Barbour Coat for a Saturday Spring Brunch. Then, throw em together with a deep blue suit, a pattern spread-collar shirt (gingham perhaps), and go out with a sharp, yet understated and casual look.
Traditional Wingtips have truly lasted the changing trends. The design, wing-curve, and perforated detailing have for the most part stayed consistent. This pair of red brick-brown wingtips from Antonio Mauritzi updates the tradition with a more dominant sole, for an authoritative edge. I wear these with forest green cords, this striped, contrast collar shirt, tie, and a charcoal wool suit jacket for a weekday office look. On Summer Fridays go casual with a pair of cuffed Jeans, a striped collarless shirt, and a waist-coat for a refinely laid-back office look. You’re going straight to the Hamptons afterwards anyway, right?
These black dress shoes may not strike as the traditional definition of a wingtip, lacking the iconic w-curve, but the perforated detailing on the toe definitely call to mind the historic shoe. It’s updated with a modern shape, not too pointed, but sharply curved for sleek elegance. Wear this with the full charcoal grey suit from above, White Spread-Collar, and a grey knit tie for special evening events that require a sharp, traditional look with a hint of detail.
When in doubt just wing it.