8 Best Wingtip Shoes (Review) In 2022

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.

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 men’s 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. 

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.

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.

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.

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.

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.

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.