Whether you call them wingtips of brogues, the ultra-stylish pointed dress shoe is a favorite of men everywhere. Why? It’s perfectly classic and undeniably fashionable, and they’re also built by companies that understand what gentlemen want: long-lasting, high-quality shoes that they won’t have to replace in six months like a pair of beater trainers. These are the best wingtip shoes, made by the best brands that are built to last through every board meeting and soiree that you attend. It’s time to suit up.
The Best Wingtip Shoe
Now there’s a mouthful. Wingtips are traditionally America southern-inspired in their design with designer holes throughout them, but Dream Pairs have put together a series of nine different styles and designs that really apply to every style. (our personal favorite are the Prince 6 Black version).
Made with classic style in mind, Dream Pairs Bruno Marc Moda Italy Classic Wingtip Shoes are made with an inexpensive faux leather, and feature a latex footbed for additional support on top of your 1” wooden heel. The latex isn’t perfectly sealed, so if you do have a latex allergy, this pair isn’t recommended for you. Rough leather laces rest on the front, while a thick stitching pattern around the platform really make every style shine. Reinforced heel cups offer support and ensure there’s no sagging with age, but just be sure to have a comfortable pair of socks to pair with these shoes. Feel free to wear them to work as office shoes.
1” wooden heel height
Faux leather lining w/ latex footbed
Durable leather lacing
Available in 9 different unique styles
- BrandDREAM PAIRS
Leather isn’t the most breathable material out there, but damn does it look good draped around your feet. That being said, Stacy Adams wanted to keep that lusty leather look that wingtips have, but they didn’t want an overly hole-ridden design. The result of that conflict was proper hole placement for perfect breathability in the toe box, and a style that doesn’t focus on them as a focal point.
Stacy Adams Tinsley Wingtip Lace-Up Oxford Shoes also have a cushioned memory foam footbed, so you’ll be able to sink into comfort after a few uses have contoured the foam to your foot shape. There’s a weird sizing system at work though because they direct you to order size-ups in certain circumstances instead of just making the shoes fit perfectly in the first place. Be sure to pay attention to ordering information. Choose from nine different styles and lace-up. With a five-way leather strip lacing system and a wide tongue, these dress shoes are easily adjustable and offer a wide range of comfortability. The wooden heel puts a bit more pep in your step and blends seamlessly into the exterior design.
Full leather construction
Criss-cross etching provides superior traction
1” wooden heel height
Each design is very breathable
- BrandStacy Adams
- Weight 12 ounces
Rockport is basically the go-between for formal and casual, and fall in a great price range at the same time. These shoes are fully waterproof right up to the tongue, you just have to ensure that they’re on nice and tight, so they don’t sneak between the tongue and upper. The heel isn’t normally built into the design like this (slight color change shows adding it on later), but Rockport’s Essential Details looks nice and cohesive.
That heel measures at 1.25”, so there’s a little more life in your step. There’s a great deal of attention in the traction padding on these shoes, which you can see in the outsole when you flip it over. Pressure-activated grid webbing allows you to prevent slippage and regain control a lot easier in less-than-ideal conditions. With a cushioned collar, there’s little to no ankle irritation from wearing these for extended periods of time. Hydro-Shield waterproofing allows you to walk with flexible comfort and full control, while the synthetic insole cushions nearly all the pressure that you receive from every step. They make a cool looking business casual shoes.
Comfortably padded collar for additional comfort
Heel w/ excellent traction measures at 1.25”
- ModelEssential Details WP Wing Tip
- Weight12 ounces
Never heard of Florsheim? After this, you won’t be able to forget about them. Slip into a den of comfort with a memory foam footbed, which contours to your foot shape after minimal use. You can rest assured that everything you’re doing is going to be padded and protected, especially when you look at the durable tongue and brogue upper.
Everything encases your foot in protection, but as we’ve said before, leather usually isn’t the most breathable thing that you could ever wear. That’s why Florsheim added SuedeTec lining in Montinaro Wingtip Dress Shoe, to add to their breathability and wick away sweat as it crops up. Evenly placed holes in the toe box of these shoes ensure little bursts of air keeping you dry at all times. Overall, it’s a solid construction. A leather design, slightly raised wooden heel, and a grand look in black or brown. The non-marking outsole keeps you in total control while walking in these beauties, while the classic oxford design keeps your style on point. For more casual look, check out our guide to the best dress sneakers and pick your perfect pair.
Fully 100% leather construction
Non-marking synthetic outsole
Memory foam footbed for a touch of added comfort
SuedeTec lining makes these ultra-breathable
- ModelMontinaro Wingtip Ox
- Weight12 ounces
It looks like Allen Edmonds Men’s McAllister Wingtip Shoes were carved out of stone; they’re flawlessly designed shoes that get some of the best points for aesthetics from any shoe manufacturer out there. The six-eyelet design keeps everything looking dapper as can be, while the intricate design around the entire shoe makes you stand out (in the best possible way).
As we climb down the list from the top, a few quirks will pop up. For Allen Edmonds, its their insoles. They’re made out of leather, so you know they’re going to hold up against the test of time, but they aren’t the most comfortable thing. You should purchase an additional insole to slip in for comfort and shock absorption. They hit home on style though, with five different unique designs and colors to choose from. Each still has that same nearly flawless stitching pattern on the platform, as well as the perfect collar support to make your days at the office a little more enjoyable.
Full leather construction
Six-eyelet lacing system looks dapper as can be
360-degree welt design looks cohesive as can be
Leather insole keeps everything nice and sturdy
- BrandAllen Edmonds
- Weight4 pounds
Cole Haan has a way with shoes, and their wingtips are no exception. With a synthetic insole and unique brogue design on the outside, you’ll get a mixture of different features as you wear Cole Haan Men’s Cambridge Wingtips. Brogue perforations along the collar, upper, and grooved along the toe box will create a nice flow of air as you take each step.
Speaking of grooves, there’s a unique pattern of traction padding on the bottom. Grooves run from side to side along the bottom of the toe box for superior sticking power, while the heels of your wingtips are solid wood and give you a ton of support. There’s always a catch though, isn’t there? Limited sizes, and wide price gaps in between said sizes. The smaller your feet are, the more money you’ll save. Seam stitching is almost entirely invisible, and your collar provides some great support for your ankles. They would also make a nice and stylish pair of shoes for teachers.
Brogue collar for aeration
1.25” tall wooden heel
Rigid grooves for traction along the bottom
100% leather construction
- BrandCole Haan
- ModelCambridge Wing Ox
- Weight4 pounds
Tri tone isn’t just a fancy title; look at these glorious wingtips. You’re certainly not going to look like anybody else at the board meeting, but it’s done in a uniquely stylish way that won’t take away from the rest of your look. With a reinforced heel cup, you’re granted a ton of support without having to solely rely on the heel for stability.
They played it smart on the brogue design. Perforations trail around the edges of each tone, including the heel cup, so it looks like the leathers are cascading from the bottom to the top. It’s an intelligent move for aesthetics, but Asher Green didn’t just focus on how these look. Asher Gren Men’s Tri Tone Calf Leather Wingtips are comfortable as can be with a synthetic insole, but they don’t offer a ton of traction. The bottoms provide almost no slip resistance, so you’ll have to rely on your own center of gravity for that. Basically, don’t wear these on a rainy day. Instead, pick some of the best rain boots from our list that will keep your feet dry.
Tri tone design ensures you won’t look like anybody else at the shindig
Constructed with leather outer and a synthetic insole
Reinforced heel cup keeps you supported and comfortable
1.25” wooden heel height
- BrandAsher Green
- Weight4 pounds
It’s tuxedo time. These slightly glossy wingtips are best suited for formal affairs, but you can rock them at just about any time. Jean Yves Dress Shoe Wingtips are fitted with an E-Z anti-scuff feature, which allows you to buff them out fairly easily. The grooved heel acts as your traction on the bottom. The rest of it offers mild traction, but nothing that’s groundbreaking. With a five-eyelet design, you’ll be able to lace up and adjust your fit on the fly.
The upper also has a great feature that means it won’t show creases, even when your shoes aren’t stores properly (or your kids put their shoes on top of yours in a shoe storage and you don’t realize it until the next day), so it’s a nice little add-on to the list of features. They’re built to last for years with a bit of TLC.
Anti-crease upper design
Wide five-eyelet design
E-Z scuff cleaning technology
Grooved heel grants you a bit more traction on slippery surfaces.
- BrandJean Yves
Wingtip Shoe Buying Guide & FAQ
How We Chose Our Selection Of Wingtip Shoes
Brand – Shoes are one of the most counterfeited items in the world, because people are willing to pay big bucks for big brands. Well, branding is important, but so is authenticity. We’ve done our homework to ensure that these shoes come from genuine retailers with authorization to sell them, so you know you’re getting the best of the best with no questions asked.
On top of that, we also many authentic brands that just weren’t producing the best wingtips out there. It’s amazing what happens when you delve deep into the reputation behind top brands, and those didn’t make the cut for this list. We went hard on which brands would and would not make the list, and what’s left is the cream of the crop for you to choose from.
Price – Price will always dictate purchases, even if you’re after the best quality in the world. There are some shoes that just aren’t worth it, but you can’t deny that price doesn’t also attribute to the durability and quality of shoes, either. We’ve done our best to find the sweet spot in the middle, so you don’t have to dance between different shoes with vastly wide price gaps.
Reviews – User reviews aid us in determining what’s worth testing, and what isn’t worth our time. You wouldn’t believe how insightful some intelligible reviews can be when you’re trying to discover the merit of a brand or the quality of a product. We use this information to decide what we’re purchasing and testing ourselves, and it’s an integral part of our process.
Features To Look For In Wingtip Shoes
Comfort – Just because wingtips are stylish as can be doesn’t mean that you have to sacrifice your comfort for that classic look. You should absolutely factor comfort into your purchase, and thankfully, there are a lot of brands out there with cushioned collars, memory foam footbeds, and contoured insoles made of highly durable materials, all with the aim of making these shoes something you want to walk in, not just need to.
Quality – It’s a pretty ambiguous concept, but quality, in our eyes, comes down to how much stress a pair of shoes can take, its durability, when it will look worn-down, and how well comfort stands up over time. Quality is how you decide what a good price is, so pay attention to the design (not just aesthetics) of a shoe, the stability it offers for your ankles and arch, and how easy they are to clean and maintain. Avoid high maintenance products whenever possible.
Material – Materials are where it gets tricky. Leather is leather, right? Wrong. There’s suede, genuine, top grain, and the list goes on and on. Furthermore, when you’re talking about insoles, you’ll see synthetic pop up a lot. What’s that about? It just means anything that’s not a naturally-occurring material.
For instance, leather is naturally-occurring, so they would specify that, but with a synthetic insole you just have to include any synthetic material and you can call it a day. Pay attention to the fine details here, because materials matter.