How to Choose Comfortable Dress Shoes for Men

Dress shoes were synonymous with looking good, but not always with feeling good—at least, not until the recent past. Thankfully, many comfortable and even orthopedic dress shoes for men have hit the market in recent years, offering many options for professional men. Follow our seven suggestions below to choose a comfortable pair of men’s dress shoes.

  measuring foot size

Get your feet measured.

The first step to choosing comfortable dress shoes for men is selecting the right fit, and the first step in choosing the right fit is knowing your true size. You can measure your feet on your own at home using a tape measure, or you can use the metal devices commonly found at shoe stores the next time you’re out shopping. If you’re struggling to measure your feet on your own, get someone to help you or seek out a shoe professional.

Try out a wider shoe.

If a shoe is too tight across the laces (or across the top of the foot, if the shoe doesn’t have laces), don’t automatically reach for a larger size. In many cases, you don’t need to fully size up, as the shoe will then be too long and slide around. You may simply need a wider version of the same size. Men’s extra wide dress shoes give you the width you need across the foot so you can walk in comfort, without the top of the shoe pinching your foot.

adjusting orthotics sole 

Don’t ignore arch support.

No matter how great a shoe looks, it will be extremely uncomfortable to wear if it doesn’t provide the proper arch support. As you try on the shoe, be honest with yourself if it gives you enough cushion. (If it doesn’t, you can add some inserts; more on this below.) Arch support is especially important if you’re looking for men’s dress shoes for plantar fasciitis, as this involves inflammation of the tendon along the bottom arch of your foot. Properly supportive shoes can help treat plantar fasciitis pain in the short-term and even prevent it.

Make sure the heel doesn’t slip.

Blisters, rubbed skin and other unpleasant minor injuries are usually caused by shoes that are too loose and thus chafe against the skin. Make sure to try on the shoe with the type of socks you would normally wear with it and then walk around to determine if the heels slip or not. When in doubt, opt for a thinner sock, as a thicker sock will artificially pad the heel so you won’t be able to tell how much the heel of the shoe really moves.

Watch out for thick seams.

While thick seams and lots of top stitching add a decorative touch to dress shoes, they can cut into your foot as you walk if the leather and stitching are stiff enough. Not every dress shoe with distinctive seams has this problem, especially if the leather has been treated so it’s on the softer side, but if the shoe has a lot of stitching, it’s worth trying it on and bending it to make sure the seams conform to your foot rather than cutting into it.

 dress shoes

Look for adjustable features.

The shape and size of your feet can change slightly from day to day, whether it’s due to swelling or just wearing extra thick socks in winter. Shoes that have some kind of adjustable features—whether that’s laces, Velcro straps, buckles, zippers or elastic inserts—will help you accommodate these minor changes so you can stay comfortable whenever you wear your dress shoes.

Consider inserts, custom or otherwise.

Comfortable dress shoes for men don’t always come ready-made out of the gate. If you’ve found a shoe that has an otherwise perfect design and fit, but the sole doesn’t offer enough support, all is not lost. Insoles, orthotics and shoe inserts can help provide extra cushioning and support in an existing pair of shoes. You can buy an orthotic insert that is designed to fit in any type of shoe or use your custom orthotics to add support that’s exactly tailored to your individual feet.

If you’re looking to buy a pair of comfortable dress shoes for men, look no further than this guide. These seven guidelines will help you choose the perfect pair that will keep you looking and feeling good all day long.

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