A quality pair of dress shoes is a wardrobe staple that shouldn’t be sacrificed for budget or comfort. That’s why we’ve combed through market research, in-house testing insights, and product descriptions to round up our favorite comfortable dress shoes for men. The brands featured here are backed by expert shoemakers and have a strong focus on quality construction that will stand the test of time.
We’ve also included a list of criteria to keep in mind when shopping for men’s dress shoes, including whether you’re looking for a high-fashion pair that skews more formal or if you want something more casual. Finally, we’ve thrown in a couple of dress shoe hacks and tips to help keep your investment fresh.
Ultimately, the best comfortable dress shoes for work are ones that can be worn with both your favorite chinos and your business attire. To make that possible, look for a style with a flexible sole that can bend and move with you, and a soft, folded tongue flap to prevent your foot from rubbing against the inside of your shoe. You’ll also want to avoid anything with a stiff or hard sole, and opt for one that has a slightly raised heel for added comfort while standing all day.
One of the most popular options is a lace-up oxford with a classic wingtip design. Cole Haan is a great choice, as they offer several styles with this construction and are made to last. They also have a comfortable OrthoLite footbed, which minimizes shock during walking.
Another option is to go with a loafer. You can find a few great pairs by Johnston & Murphy, who are known for blurring the lines between formal and casual. Their Griffin cap toe Oxfords are a good example, and they can be paired with either a suit or a pair of chinos.
You can also look for a pair with a double monk strap to add a touch of elegance. Magnanni is a brand that makes leather dress shoes for less than you’d expect, thanks to their direct-to-consumer sales model and an in-house team of artisanal craftspeople. Their Corey Oxfords are perfect for office-appropriate looks, and they feature both Blake and Goodyear welting for long-lasting wear.
If you’re on a budget, Dr. Scholl’s has a great pair of dress shoes for under $100. They’re benchmade in Italy, and their oxfords have the same comfort features as some of the more expensive options on this list.
If you’re willing to spend a little more, we recommend checking out Beckett Simonon. The brand offers both Blake and Goodyear welts, and their leather is some of the best on the market. They’re also benchmade by expert artisans, so you can count on them to be durable and comfortable. They also have a wide range of color options, so you’re sure to find a pair that suits your style. The only downside is that they run narrow, so you may need to size up a half size.