Wingtip Shoes Are the Versatile Footwear You Need Right Now

They'll Match Any Outfit, Mood, and Occasion

bird's eye wingtip dress shoes gray slacks

B. HARVEY / Stocksy

Despite its tradition in men's footwear, wingtips today have transcended the boundaries of shoe gender. Increased demand for wingtip shoes has resulted in more and more brands creating both women's and unisex offerings. Some of our favorite celebs and It-girls can be seen wearing this versatile style, and even though there are still plenty more pickings in the men's department, that shouldn't discourage you. Instead, think of it as motivation to learn how to convert men's and women's shoe sizes and multiply your footwear options tenfold. All that to say that no matter your taste or style, there are a pair of wingtips out there for you.

Have we piqued your interest in wingtip shoes yet? Keep reading to learn more—including our favorite styles.

What Are Wingtip Shoes?

Blue checked maxi skirt with black and white Dr. Martens wingtips

@nrk_0304 / Instagram

Before we go jumping ahead into when wingtips got their start and how this footwear trend is being worn today, let's pause to clarify what it is that actually constitutes a wingtip shoe. Wingtips have a characteristic pointed toe cap that spreads toward the sides of the shoes. This design creates a shape that somewhat resembles wings, hence, (you guessed it) "wingtip." The toe cap is usually ornamented with perforations of varying sizes, which although purely decorative nowadays, had a practical purpose at one point.

History of Wingtip Shoes

In a way, wingtips are the OG of Crocs. Their perforations were originally incorporated to allow water to drain from the shoes after walking through wet terrain. Known as brogues in Europe, they originated in 16th century Ireland as a type of outdoor country shoe that men would wear while hunting or shooting because they were sturdy and could handle the rugged landscape. In fact, brogue derives from the Old Irish word for "shoe:" bróg. And while they were not considered appropriate for any other occasion besides being outdoors, that changed by the end of the 19th century. The invention of Jan Matzeliger's shoe lasting machine in 1883 increased the production of shoes and decreased their cost, thereby ushering them into mainstream fashion.

In the early 1900s, wingtips became known as sporting shoes thanks to the Prince of Wales, who wore a pair of two-toned wingtips (a.k.a. "spectators" or "co-respondent") during a golf outing. Screen legends Fred Astaire and Gene Kelly also popularized the shoes in their famed dance routines. Actresses Katharine Hepburn and Marlene Dietrich made a statement—fashion and otherwise—when they dressed in this classic style typically reserved for men. The saddle shoe, a variation of the wingtip, features black or brown leather over the instep and emerged in the 1950s. It was made famous when Elvis Presley donned a pair in the film, Jailhouse Rock. Model Twiggy continued the women-for-wingtips trend in the '70s, which has recently been revived among fashionistas today.

Types of Wingtips

All wingtips are characterized by the perforated toe cap, but there are a few different types:

  • Full wingtips have a winged toe cap with a fair amount of decorative perforations.
  • Spectator shoes are a type of full wingtip that uses two-toned color combinations.
  • Longwing or American brogues look just like full brogues, but the wings extend the full length of the shoe and meet at the center seam at the back of the heel.
  • Semi or half brogues include decorative perforations that are just on the toe cap.
  • Ghillie brogues don't have tongues, but long laces that wrap around the ankle. This is a very traditional style that is worn with formal Scottish dress.
  • Quarter brogues feature perforations along the edge of the toe cap that isn't decorative. They are more understated and considered the most formal type of brogue, more so than semi or full brogues.

How to Wear Wingtips

Today's wingtips seem to have it all. Classic iterations (think: leather dress shoes) offer a timeless elegance that presents a stark contrast to their rustic past. Still, broguing may deter some traditionalists from wearing wingtips to a formal event; hence, the audible gasps when Prince William stepped out in wingtips at his royal wedding. Whether intentional or not, his fashion faux pas taught us something: Fashion follows no rules but rather, evolves.

Contemporary shoe designers are now crafting wingtips to suit any occasion. As such, they come in a wider range of materials, from leather to canvas, so you can dress up or down as you see fit. To us, they're the perfect show-off shoe that can pair well with any outfit or mood. So whether you're headed to the office or perhaps out on a date, consider wingtips to top off your look.

Shop Products

Best Overall

Dr. Martens platform spectator shoe

Dr. Martens

Dr. Martens 3989 Bex Smooth Leather Brogue Shoes ($140) takes a vintage look and gives it a breath of new life. The two-tone spectator is stylish enough but, when combined with a rubber platform, becomes head-turning—not to mention comfortable. We give it bonus points for being a unisex style.

Best Booties

Chelsea boot with broguing


The wingtip on this Bullboxer Ellie Wingtip Chelsea Boot ($55) adds an extra detailing that makes it stand out among just any old booties. They also hit the C-trifecta: casual, cool, and comfortable. While that's a win in itself, these Chelsea boots will also complement jeans, dresses, skirts—and then some—elevating your fall and spring wardrobes.

Best Oxfords

Pink metallic oxfords

Cole Haan

If you haven't slipped on a pair of Cole Haan ØriginalGrand Energy Twin Oxford ($180) yet, what are you waiting for? Wearing these shoes feels like walking on air. Meanwhile, the soft rosy hue gets some edge with a metallic finish. And since it's all about going monochrome these days, consider pairing with Millennial Pink hair.

Best Derbies

Black suede wingtip shoes with wooden heel and sole


We love these Ecco Sartorelle 25 Tailored Women's Shoe ($160) thanks to their versatility. They're formal enough to wear to the office while also being perfect for any post-work play. And don't be intimidated by the suede material, which is easier to clean and protect than you might think (the black color also helps).