The 9 best men's dress shoes for stepping out in style and comfort

Business Insider

10-06-2025

Dress shoes don't have to be stuffy or relegated to the odd wedding or other formal occasion you find yourself attending. They're actually a very versatile footwear category that can elevate your everyday style and still be appropriate for more formal occasions. Knowing what to look for in both the type of shoe and how they're made is key to finding a high-quality dress shoe within your budget.
This guide highlights some of the best in dress shoes for men, from the least formal — loafers — to the most formal, wholecut Oxfords, with some others that range between these two. That is, brogue wingtips, dress boots, Bluchers, and monk straps. We've also included both a high-end Oxford from the legendary American brand Allen Edmonds that's worth the monetary investment, and a more budget-friendly pair from Florsheim, which are still manufactured with high standards using time-tested techniques.
We've thoroughly tested these dress shoes that will have you looking sharp, feeling confident, and will last for years with a little TLC on your part.
Best Oxford: Ace Marks Wholecut Oxford
A wholecut Oxford offers one of the dressiest shoe options out there with its closed lacing system, refined profile, and sleek style that pairs well with everything from a tux to a business suit to more casual separates. Ace Marks offers an exceptional Plain Toe Wholecut Oxford, which the DTC brand handcrafts in Italy from a luxurious hand-dyed and burnished calfskin leather and includes key details like a leather lining, stacked leather heel, and Blake stitching so the shoes can be resoled when the time comes (although based on our testing these Oxfords that run true to size will last you years before you'll need it).
Best for comfort: Cole Haan Zerogrand Remastered Wingtip Oxfords
Cole Haan's Zerogrand Remastered Wingtip Oxfords masterfully combine the elevated style of wingtip Oxford dress shoes with the comfort of sneakers in one stunning package that doesn't require breaking in. I walked two miles in these straight out of the box and my feet felt fine, with no pinching, rubbing, or blisters — and they've only gotten more comfortable over longer wearing periods, including an eight-mile walk around Manhattan.
Best Brogue: Beckett-Simonon Yates Oxfords
The brogue dress shoe features perforated leather detailing, and whether it's a full brogue wingtip — with a point at the center of the toe cap and wings running along the sides — a half-brogue, with broughing at the cap toe, along the shoe's edges, and with a medallion, or a quarter brogue, which doesn't feature a medallion, these various iterations add visual appeal to your footwear. The Durant Oxfords are full-brogue wingtips handcrafted in Columbia under ethical conditions, feature full-grain Italian leather, gorgeous details and craftsmanship, break in easily, and are made to order, which allows the company to offer a superior shoe at a reasonable price. (Note: Beckett-Simonon shoes are made to order and include 150 steps in the manufacturing process, which means it can take between six to eight weeks for delivery, but it's worth the wait).
Best Loafer: Marc Nolan Abe Penny Loafers
Loafers, whether bit, tassel, or penny, are the warm weather shoes that offer an elegant way to dress up a casual outfit or make a suit seem a bit less stodgy, and the penny loafers from the DTC brand Marc Nolan do the job exceptionally well with 11 different options in eye-catching colorways and materials. They exude summer fun without losing a sense of sophistication thanks to their top-notch materials, like calfskin leather and sheepskin suede, and are easy to break in, very comfortable due to memory foam insoles, and can be worn with or without socks.
Best Budget Dress Shoe: Florsheim Midtown Cap Toe Oxford
Andrew Amelinckx
Florsheim's Midtown cap toe Oxfords nicely balance price with quality that, like all the footwear I've tried from the brand, hold up well, with the bonus that they're really comfortable for all-day wear and are available at Famous Footwear. For $125 you get a great looking dress shoe made from leather sourced from environmentally responsible tanneries with Goodyear welted construction (meaning it can be resoled), plus tons of cushioning, and they'll hold up well for years if properly cared for.
Best Luxury: Allen Edmonds Park Avenue Oxford
The word iconic gets thrown around a lot, but in the case of American heritage brand Allen Edmonds and its Park Avenue cap toe Oxford, it's an apt description and while they're considered luxury, the craftsmanship and top-notch materials justify the cost. They handcraft these timeless dress shoes in Wisconsin using 212 steps, European calfskin, Goodyear welting, and cork insoles that mold to the shape of your foot over time, making for a refined pair of Oxfords that deliver a comfortable wearing experience, will last decades, and can be recrafted down the road.
Best Dress Boot: Idrese Galahad Jodhpur boots
Idrese is a direct-to-consumer shoe company that handcrafts its footwear in Spain, and while it specializes in letting the customer design their own shoes and boots — that's what I did with a pair of Jodhpurs that I absolutely love and fit my feet perfectly — the company also has ready to wear items like the Galahad jodhpurs. Idrese uses supple Italian calfskin leather, Goodyear welting, and a sleek profile for an elevated take on this boot style that includes a strap and buckle near the top.
Best Derby: Moral Code Chase Derby
Best Monk Strap: Thursday Boots the Saint Double Monk Strap
With their rich history dating back centuries to their modern appeal as an alternative to less fashion-forward Oxfords, monk strap dress shoes — with their unique straps and buckles (one or two) rather than laces — look as good with a contemporary suit as they do with nice jeans, so they won't get dusty waiting for formal occasions to be worn. The DTC footwear brand Thursday Boots makes the Saint double-monk strap from sleek full-grain leather using Blake stitching, with straps that are sturdy, stay in place, and have a good range of adjustability for a tighter or looser fit — and all with a minimal break-in period.
What to consider when shopping
There are a few important factors to consider when looking for dress shoes that will last you years. The shoes should be made of high-quality leather rather than a synthetic material (unless you're morally opposed to it). The shoes should have either Goodyear welting or Blake stitching, rather than being cemented, as you see with sneaker construction. These two old-school techniques for attaching the upper to the sole, allow you to have them resoled down the line.
FAQs
What's the difference between Oxfords and Derbies?
Oxford have closed lacing, meaning the part of the shoe called the quarters, where the laces go, are sewn under the vamp (front part of the shoe) making for a sleeker shoe that's considered more formal than Derbies. The latter type of shoe has open lacing, meaning the quarters are sewn over the vamp, which gives the shoes a more relaxed look and allows for greater ease of movement.
How do I care for leather dress shoes?
There are a few simple steps to keeping your dress shoes looking sharp. Depending on how often you wear them, you should shine them every few weeks if they get heavy use or every few months if you don't wear them as often. First, clean them with saddle soap, then use a moisturizing cream polish, and if you're looking for a high shine, use a wax polish. Here are the six you should use.
Can dress shoes be resoled?
Quality dress shoes should be made with either Goodyear welting or Blake stitching, two methods for attaching the sole to the upper. Both of these methods allow for a professional cobbler to resole your dress shoes.
Are expensive dress shoes worth it?
It depends on what your needs are and whether you're willing to invest the money. If you can afford to, you should buy a well-crafted, timeless style of dress shoe rather than a cheaper fast-fashion pair that uses glue instead of Goodyear welting or Blake stitching. A high-quality pair can last years, if not decades, if properly cared for, while cheaply made ones won't last nearly as long.
How do I break in new dress shoes without pain?
There are a few tricks you can use to break in new dress shoes. If you aren't in a big hurry you can do it over several days starting by wearing them indoors for 30 minutes or so and then over the next few days, wear them for incrementally longer periods, both inside and outside. Comfortable socks also help and if you know you're prone to getting blisters on certain parts of your feet, you can stick adhesive bandages on the problem spot until your new shoes become comfortable.