11 Best Wingtip Shoes for Men in 2020 – Buyer’s Guide & Reviews

best wingtip shoes

Popular since the beginning of the 19th century, brogue shoes were originally worn in the Highlands of Scotland, UK. They were characterized by the perforated holes on the front and sides of the leather. The holes meant that men working out in the countryside could walk through streams and rivers, without their shoes soaking up the water.

Now a staple of men’s fashion, the wingtip is the traditional brogue’s younger, trendier brother. In this article, we’re going to discuss: what are wingtip shoes, different types of wingtips, how and when to wear them, and, ultimately, review the best wingtip shoes for men of 2020.

So, we already know that brogues were the starting point of this shoe style, with the perforated holes being their defining characteristic, but what are wingtips and why do we call them that?

Simply put, wingtips are a particular style of brogue, but rather than having the holes go across the shoe, as is typical for classic brogues, the wingtip refers to the pointed shape that appears on the cap of the shoe, so-called because it resembles the wings of a bird.

A common misconception is that wingtips are formal dress shoes, only to be worn on the fanciest occasions, but we’re about to put that myth to bed. Wingtips are an essential part of any man’s wardrobe. Stop letting them gather dust at the closet’s back, waiting for the next wedding or funeral. It’s time to bring those fellas out and let them be the star of the show.

Different Styles of Wingtips

The great thing about these shoes is that they’re versatile and can be worn with a host of different outfits.

Even though the name refers to a brogue style, wingtips themselves have multiple designs and levels of formality. A general rule of thumb is: the more holes, the more casual the shoe.

Traditionally, formal dress shoes were made using one piece of leather, so the leather in question had to be as close to perfect as possible, and perfect equaled expensive. Therefore, something like a classic Oxford shoe, which is made with one piece of leather and may or may not have a plain or perforated line going across the top of the shoe-cap, are more expensive and considered a more formal style.

Whereas wingtips can use up to four leather pieces, making them more cost-effective to produce and are therefore considered more casual. Now let’s break that down a little bit more:

  • Traditional wingtip: these will have the perforated ornamentation (holes) going around the base until the shoe-waist and coming to a point on the top of the shoe-cap. They may also have ornamentation around the top-line (throat) of the shoe.
  • Longwing: Like the traditional wingtip, they will have the same pointed design on the shoe-cap, but the ornamentation on the base will continue to the back of the heel. These are considered less casual than the classic wingtip. Remember: more holes equals more casual.
  • Two-tone wingtips: this refers to having two colors on the same shoe, usually with the outer-pieces contrasting with the base color. These are considered more casual still, as a pair of plain black or brown shoes is immediately more formal than shoes with more than one color.

How to Wear Wingtips

We’ve already established that wingtips are casual shoes, right? So you could swap out your sneakers for wingtips and wear them with shorts, correct? Absolutely not. While wingtips are considered more of a casual style, they are still dress shoes and therefore are semi-formal. Let’s use the term “casual dress shoe” from now on.

When to Wear Wingtip Shoes

So when do you wear casual dress shoes? If you take weddings, funerals, and black-tie galas off the table, you’re left with most professional and social settings where casual dress shoes and, therefore, wingtips would be a perfect choice.

Brown wingtips are probably the most versatile, as you can wear them with almost every color pants. Try a pair of brown wingtips with dark denim jeans or light-colored chinos for a casual-yet-smart occasion. Or dress them up a bit with wool pants or a suit. Just avoid black suits, as they would be considered too formal and would work better with a classic Oxford shoe.

From office drinks to family dinners, wingtips are your go-to choice for any smart-casual event. And, if you want to add a bit of panache to your outfit, consider a two-tone shoe to bring a bit of flair to proceedings.

What to Look For When Buying Wingtips

When shopping for any shoes, you’re looking for the perfect combination of quality, comfort, style, and price. It is no different when looking for the perfect pair of wingtips. Consider the quality of the soles; the leather used to make the body of the shoe, whether is has a cushioned inner lining etc. Designer fashion brand doesn’t necessarily mean better, but making sure your shoes have been well made by a reputable manufacturer, using high-quality materials, is key to investing in the right pair of wingtips.

Now, let’s look at 11 pairs of the best wingtip shoes that you could add to your collection today.

Comparison Table

Product

Material

Price

11 Best Wingtip Shoes for Men in 2020 – Buyer’s Guide & Reviews 5

Material: Leather

Leather

The 10 Best Wingtip Shoes for Men of 2020

1. Stacy Adams Tinsley Wingtip Oxford

FEATURES

  • Buffalo leather upper
  • Breathable leather linings
  • Cushioned memory foam insole
  • Various colors options

Available in a wide range of colors, these classic lace-up wingtips are a great mix of quality and style at an affordable price. 100% leather means they will be comfortable and breathable, and with the memory foam cushioned lining, you’ll be able to bounce around all day in these.

PROS

CONS

2. Rockport Essential Details Waterproof Wingtip

FEATURES

  • Leather
  • Rubber outsole
  • Hydro-Shield® construction offers waterproof leather,
  • Rockport’s truTECH® lightweight comfort system

An affordable option, these longwings are an easy choice for a smart-casual shoe. They come in black, brown, and tan, so not the most exciting selection, but they are a firm favorite among buyers.

The style is a little rounder than some other options, giving them an even more casual look, which is great if you’re looking for shoes that pretty much go with everything.

PROS

CONS

3. Cole Haan Williams Wingtip Oxford

FEATURES

  • 100% leather uppers
  • Leather sole with wheeled welt and rubber forepart
  • Fully lined

Very well made and modestly priced, these are an excellent choice of wingtip for the man who likes to keep things simple and stylish. The classic shape and design is very elegant, with no frills or fusses, just very well-crafted shoes.

The selection on offer is only black or tan. While there’s no option to dazzle your date with an audacious color-combo, these are a testament to beauty in simplicity – absolutely classic wingtip shoes.

PROS

CONS

4. Lethato Wingtip Brogue Oxford

FEATURES

  • 100% Handcrafted
  • Argentinian full-grain leather uppers
  • Hand-painted
  • Cushioned insoles
  • Various colors options

Moving away from the old-school classic, we’re now talking about cool wingtip shoes. With a vast array of styles, you’re bound to find one that catches your attention and, with a selection that includes green, wine-red and purple, this could be your chance to dive into uncharted waters with your fashion statements.

Added details like golden metal shoelace tips and hand-painted soles mean these wingtips pack a little more punch than most others out there.

PROS

CONS

5. Allen Edmonds McAllister Wingtip Oxford

FEATURES

  • Lined premium calfskin leather upper
  • 6 eyelet lacing
  • 360º Bench Welt construction
  • CustomCork™ insole
  • Black Dainite rubber sole
  • Made in the USA

Raising the bar (and the price) is another collection of classic wingtip brogues. This revered and experienced manufacturer has been making shoes in Port Washington, WI, since 1922 and still uses the same workbench as they did almost 100 years ago.

As you would expect, the shoes are handcrafted and 100% leather. The selection is made up of the traditional color-scheme you would like to see from a classic shoe-maker and, if you’re a fan of supporting local business, these brogues are an all-American dream. Being high quality and US-made comes at a price, though.

PROS

CONS

6. Ecco Vitrus Wingtip Tie

FEATURES

  • ECCO hand treated calf crust leather
  • Soft leather lining
  • Rubber sole
  • Forefoot covered in cork layer
  • Molded inlay sole
  • FLUIDFORM™ technology 

A slightly more modern twist on the classic, Vitrus uses fluid foam injection technology to give your feet more comfort and support and, in their own words, creates “a perfectly anatomically designed platform that mirrors the contours of your foot.”

The materials used are more varied too: leather for the shoe body, a rubber sole, and cork-covered forefoot suggest that this company is trying to make their mark in the industry by modernizing the wingtip and bringing it into the 21st century.

PROS

CONS

7. Ted Baker Deelani Oxford

FEATURES

  • 100% leather
  • Rubber sole
  • Footbed decorated with seasonal artwork
  • Layered sole featuring Ted Baker geometric tread

Another purveyor of green brogues, Ted Baker, offers their clients a few more options, including a suede longwing. All shoes are 100% leather with a contemporary layered sole, and the laces are provided in two colors, giving these wingtips just a hint of modern-day energy.

Ted Baker’s shoes enjoy positive reviews across multiple platforms and are praised time and time again for their quality, style, and variety of sizes. Price-wise, they’re at the higher end of mainstream retail but without becoming overpriced.

PROS

CONS

8. Florsheim Allis Wingtip Oxford

FEATURES

  • Leather uppers and linings
  • Synthetic sole
  • Uses Florsheim’s Comfortech technology
  • Ortholite cushioned footbed

This manufacturer is another one to go down the route of comfort as its primary concern. Florsheim uses Ortholite technology, which gives the footbed an extra bounce, while a cushioned insole also provides more comfort for the wearer all day long.

The rubber sole is flexible and durable, and they offer all of their wingtips in medium or wide width, which you don’t see in many brands. It could be said that this company has sacrificed an element of style to make their shoes so comfortable, with the designs and colors being very classic but lacking any type of verve or character.

PROS

CONS

9. Frye Jones Wingtip

FEATURES

  • 100% leather
  • Leather lined
  • Waxed fabric laces
  • Rubber sole
  • Waterproof

A very safe choice, these basic wingtips are great if you want something practical and comfortable to wear every day. With consistently good reviews, this brand is clearly using quality materials and making good casual shoes.

For a very comfortable and durable shoe, you can expect a relatively mid-range price tag too – middle-of-the-road price for a middle-of-the-road shoe.

PROS

CONS

10. Oliver Sweeney Aldeburgh

FEATURES

  • Calf leather uppers
  • Calf leather lining
  • Five eyelets
  • Leather sole
  • Made using Goodyear welted construction

Throwing their hat into the ring of luxury brogues, Oliver Sweeney brings us this beautifully crafted Oxford wingtip, complete with ornamentation on top of the shoe-cap.

Made using Goodyear welted construction, calf leather, and durable rubber soles, these should be the only wingtips you’ll ever need to buy. They enjoy positive reviews across the board, with buyers complimenting the style and quality of the shoes.

PROS

CONS

11. Paul Parkman Goodyear Welted Ghillie Lacing Wingtip Brogues

FEATURES

  • Made to order
  • Brown & camel hand-painted leather upper
  • Camel leather lining and inner sole
  • Ghillie lacing
  • Made using Goodyear welted construction
  • Double leather sole

If you love wingtips and really want to invest in your footwear, this could be the brand for you. Handmade to order, using Goodyear welted construction, double-leather soles, camel leather linings, and innersoles, the quality and attention to detail make these shoes something very special indeed.

The added detail of Ghillie lacing (which dates back to Celtic Scotland) gives these brogues that extra flash of style that may be lacking from your mainstream retailers. Let’s face it, these are not a cheap purchase that you pick up in the sales: these are expensive wingtip shoes. They are made to order and are priced accordingly, which puts them out of reach for some customers.

PROS

CONS

Frequently Asked Questions

Wingtips vs. Brogues: What’s the Difference?

Brogues are characterized by their decorative perforations across the cap and sides of the shoe. There are four main variations of this design: full or wingtip brogue, semi brogue, quarter brogue and longwing brogue. Therefore, a wingtip is simply a type of brogue.

Can You Wear Wingtip Shoes With Jeans?

Sure, you can, but remember to keep it simple. Slim or skinny jeans that cut off at the ankle work really well. Your wingtip shoes want to be seen, not ruffled up under a slack opening. Keep the simple but stylish look going all the way to the top with a t-shirt/blazer combo or a sweater.

Are Wingtips Shoes in Fashion?

Were they ever out of fashion? The beauty of the wingtip, and other brogues, is that they sit in the middle of casual and dressy, so they will always have a place in your wardrobe.

What Color Wingtips Should I Buy?

That’s a tricky one to answer. The most important thing to consider is: how will you be wearing them?

Black will always feel more formal and dressy than other colors. It’s a classic, but if you aim to complement a slightly more casual ensemble, you may find it a little restrictive. The next go-to classic is a brown wingtip. Brown fits well with the earth tones and goes great with jeans as well.

The beauty is that you don’t have to stick to one color: you could go for a subtle two-tone mix of deep and lighter brown together, for example, or if you prefer your style a little bolder, you might choose white in contrast to black or brown. The possibilities are endless!

Final Thoughts!

Buying shoes can be a bit of a minefield. There are so many styles, colors, and brands to choose from, so how do you know where to start?

If you’re someone who is looking for a good all-rounder, the wingtip could be perfect for you. You can go for the most casual style and play it safe with a simple tan design, or show off your extroverted side with a two-tone wingtip complete with cap ornamentation.

The best thing is that there’s a wingtip out there for everyone and, most importantly, for every budget. Wingtips have become a fashion staple for men for a reason: they’re comfortable, affordable, and, most of all, never go out of style.


Marilyn

Marilyn

Marilyn Chase writes fashion articles for luxury power houses that want to see their brands surge. Her articles have appeared in various North American and Western European websites. She contributes articles about design, craftsmanship and manufacturing techniques in fashion. Her articles focus on trends and research supported by first hand interviews and pictures. She is qualified by extensive experience and a degree in fashion from New York.

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