A Guide to Comfortable Dress Shoes for Men

Are you searching for the perfect pair of men's dress shoes? As you begin exploring all of the options, you're sure to find plenty of styles, designs, and materials.

The key to choosing a pair that you'll reach for time and time again is to make sure the shoes you pick don't just look good. They should also feel good.

Formalwear can often be restrictive, rigid, and stuffy, but that doesn't have to be the case. Today, we're sharing how to find the most comfortable dress shoes for men so you can transform your closet, one step at a time.

Start With High-Quality Materials

When it comes to men's shoes, there's only one material you need when you want to achieve a dressier style: genuine leather. Leather not only looks sophisticated and timeless, but it also ages well and maintains its shape over time.

While it might seem as though all leather shoes should look and feel the same, that's not true. Be wary of any "leather" shoes that feel suspiciously smooth and are shinier than your bathroom mirror. These are signs that the material isn't genuine, and likely contains a plastic base.

Looking for a sturdy pair that stands up to the test? Start with our Piqure Leather Dress Shoes! Made of real leather, these shoes are designed to conform to your foot, offering an excellent fit and unmatched comfort with each step. Available in black, blue, or brown, they're sure to become the most classic and best-loved part of your wardrobe.

Check the Toe and Heel

Men's fashion shouldn't have to be painful to look great. When picking out your next pair of dress shoes, pay attention to the shape of the toe box and the height of the heel. These are two areas where you can begin to feel tension if the shoes aren't properly designed and fitted to your foot shape.

At the toes, the shoe should walk the line between sharply pointed and squared off. Neither of those styles will give your toes the room they need to comfortably move around as you walk.

A gentle, soft curve at the toes is best, and that's exactly what you'll find with our Wingtip Gatsby Dress Shoes. The tip is perfectly curved, the stitching is supreme, and the laces are meticulously well-aligned. These shoes offer top-of-the-line comfort and style, combining insane quality with a sleek look that goes with all of your best formal wear.

For the heel, try to stick with less than one inch of height. A lifted heel is not only uncomfortable to walk in, but it can also change the overall aesthetic of your look.

That said, you do want some height to your heel, especially when wearing dress shoes. Super-flat shoes are fine in more casual settings, but more formal options usually include a slight degree of lift. All of the dress shoes in our shop meet this criterion, with some heels more defined than others.

Research the Lining and Insole

The quickest way to ruin a great new pair of dress shoes is to stink and sweat in them all day. You want your feet to stay cool and comfortable, no matter how many miles you log with your new kicks.

If possible, find a pair of shoes that features a built-in liner designed to be super breathable and ultra-soft. Moisture-wicking materials can make sure your feet stay dry, even in the most humid conditions.

For inspiration, check out our Respirer Leather Dress Shoes. Designed to look and feet more like business-casual sneakers than formal footwear, they include a liner that's even softer and airier than most sportswear shoes! For extra breathability, we even added a specially designed insole to promote constant air circulation.

Respirer Breathable Leather Shoes Brown

Opt for an Orthopedic Pair

Gone are the days when orthopedic footwear looked like orthopedic footwear! Today, you can find top-quality styles that look formal and refined but are also fitted with special features designed to make them the most comfortable shoes you've ever owned.

That was the balance we struck with our Oxford Derby Orthopedic Leather Shoes. Designed to look like top-shelf formalwear, you'd never know that these shoes were actually designed for all-day wear, with strategic additions to maximize comfort and support.

Designed in the U.S. and endorsed by professional shoemakers, these genuine leather dress shoes are durable and meant to last. They're also wildly comfortable, with features that include:

  • Breathable materials
  • Orthopedic heel
  • Slip-resistant bottom

Available in a wide range of sizes, including wide-width, our Oxford Derby shoes are perfect for any occasion. You can choose between three different color options, so you can always find a pair to match your ensemble!

Man walking up stairs in Oxford Derby Orthopedic Leather Shoes

Find the Right Fit

Finally, let's talk about sizing. It can be hard to shop online for shoes if you can't try them on in person, which is why it's important to start with the right source. When you shop with Gatsby, we offer a 30-day satisfaction guarantee and lightning-fast shipping, which makes the returns process easy.

Still, you want to strive for the ideal fit, right out of the box.

To get there, start by checking our sizing guides.

Dress Shoe Size Chart Comparison

It also helps to know your exact shoe size! If you've never measured your foot before, this quick guide can show you how. When your shoes arrive at your doorstep, here are two ways to check the size for accuracy:

  • Try them on in the afternoon or evening, because your feet swell a little throughout the day
  • Wear the type of socks you normally wear with dress shoes

Keep in mind that men's leather shoes are designed to keep their shape and won't stretch too much. If they feel too tight when you first put them on, don't expect them to fit correctly after an initial break-in period. It's best to stick with pairs that feel great as soon as you slip them on!

Shop Our Selection of Comfortable Dress Shoes for Men

Now that you know a little more about how to find the right pair, are you ready to find your new favorite pair of dress shoes? Instead of searching all over town or the internet, start with us!

At Gatsby, we offer a wide selection of comfortable dress shoes for men. As you click through the choices, you're sure to find a pair that fits your style, suits your needs, and exceeds your expectations.

If you have any questions as you shop, feel free to reach out to our team!

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Crafted By Professional Shoemakers

Our shoes are designed, tested, and endorsed by our team of professional shoemakers. We craft our shoes with the highest comfort and quality available.

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If you want to exchange or return your shoes, we offer a full 30-day guarantee so that you can try all of our styles worry-free!