We independently evaluate all of our recommendations. If you click on links we provide, we may receive compensation. Shopping Fashion Shoes The 10 Best Men's Dress Shoes The Cole Haan Original Grand Wingtip Derby won our top spot By Michelle Rostamian Michelle Rostamian Michelle Rostamian is a beauty, wellness, and lifestyle writer with nearly 10 years of experience in the beauty industry and bylines at PEOPLE, Byrdie, Real Simple, InStyle, and more. She began her career in the beauty industry as a publicist and content writer representing makeup and skincare brands as well as industry professionals. She formerly was a social media marketer. Michelle graduated from the University of California, Los Angeles with a B.A. in Communications. People Editorial Guidelines and Alyssa Brascia Alyssa Brascia Alyssa Brascia is a staff shopping writer for PEOPLE with two years of experience in the digital media industry. Her expertise lies in the realm of fashion and beauty, where she covers the best products that your wardrobe and makeup vanity need like the best lip oils, boyfriend jeans, workout sets, ballet flats, and more. People Editorial Guidelines Updated on July 30, 2024 02:00PM EDT In This Article View All In This Article Our Top Picks Reviews Others We Tried What to Know Behind the Scenes Why Trust PEOPLE? What Is PEOPLE Tested? Photo: People / Karen Chen Finding the right pair of men's dress shoes is quite a conundrum. You want something high-quality, long-lasting, and aesthetically pleasing, but oftentimes, you'll have to sacrifice comfort and fit for these features. We set out to defy the odds and search for the best comfortable men's dress shoes that truly have it all — testing out 22 pairs of men's dress shoes and narrowing it down to 10 options that all scored highly on fit, comfort, quality, and value. The Best Right Now We get it — dress shoes aren’t cheap. If you want to get right to the good stuff, we rounded up the best deals on our winners below. Cole Haan Original Grand Wingtip Derby is 40 percent off on Amazon Clarks Tilden Cap Oxford Shoe is up to 36 percent off at Amazon Clarks Bushacre 2 Chukka Boot is 40 percent off at Amazon Mephisto Edlef Slip-On is $100 off at the Nordstrom Anniversary Sale Stacy Adams Dickinson Cap-Toe Oxford is up to 43 percent off at Amazon "Whether your foot is wide or narrow, the shoe should be comfortable, and there should be room to wiggle your toes a bit," says William D. Spielfogel, New York-based podiatrist and medical advisor to The Good Feet Store. We also found excellent options for those looking for men's dress shoes for wide feet or anyone who stands all day at work or events. Whether you're a fan of an ankle boot style of dress shoe or prefer an Oxford shoe — we’ve got you covered. Below, the best men's dress shoes PEOPLE Tested. Our Top Picks Best Overall: SALE Cole Haan Original Grand Wingtip Derby at Amazon $170 $113 Jump to Review Best Budget: Dream Pairs Bruno Moda Oxford Wingtip Dress Shoes at Amazon $43 Jump to Review Best Under $100: SALE Clarks Tilden Cap Oxford Shoe at Amazon $90 $40 Jump to Review Best Oxfords: Ace Marks Cap Toe Oxford at Acemarks.com Jump to Review Best Oxfords, Cheaper: Cole Haan American Classics Montrose Oxfords at Colehaan.com Jump to Review Best Investment: Magnanni Corey Oxford Shoe at Magnanni.com Jump to Review Best Boots: Thursday Boot Co. Cavalier Chelsea Boot at Amazon $190 Jump to Review Best Casual: SALE Dr. Scholl's Sync Oxford at Amazon $85 $60 Jump to Review Best for All-Day Wear: SALE Stacy Adams Dickinson Cap-Toe Oxford at Amazon $110 $55 Jump to Review Best Slip-On: Mephisto Edlef Slip-On at Amazon $319 Jump to Review Best Overall Cole Haan Original Grand Wingtip Derby PHOTO: Nordstrom $170 $113 at Amazon $150 at Zappos View on Dsw.com Star Qualities No break-in period necessary Ample cushioning for optimum comfort Comes in a wide range of colors and sizes Red Flags Material may scuff on rough surfaces One wear of the Cole Haan Original Grand Wingtip Derby, and it's easy to see why it won our top spot. While testing this pair, we felt like we were walking on clouds — they required no break-in period, offered a supportive arch, and withstood walking and standing for a long period of time — we have the brand's proprietary Grand.OS technology to thank for that. This means that the insoles, outsoles, liners, and uppers remain flexible as you walk, dance, or stand, making the shoes incredibly versatile for different activities and occasions. Made with a leather upper and sturdy rubber soles, these high-quality shoes feel durable and long-lasting. They come in a wide range of sizes in all the color shades you need, including black, brown, blue, dark tan, and dark chocolate. One thing to watch out for: The leather material may scuff if it comes into contact with rough surfaces. These Cole Haan men's dress shoes have a round toe and classic lace-up style. They run true to size and are a great value for the price. Overall, the Cole Haan Original Grand Wingtip Derby dress shoe stood out as our Best Overall for its comfort, styling versatility, and durability. Sizes: 6.5-16 | Colors: 6 | Material: Leather upper/leather and synthetic lining/rubber sole Best Budget Dream Pairs Bruno Moda Oxford Wingtip Dress Shoes PHOTO: Amazon $43 $37 at Amazon View on Brunomarc.com Star Qualities Footbed was comfortable for all-day wear High-quality look at a reasonable price Great starter dress shoe Red Flags Not much heel or arch support As this pair boasts the lowest price on this list, we were skeptical of how such inexpensive dress shoes could look and hold up after a few wears. To our surprise, these Dream Pairs oxford shoes were surprisingly attractive and comfortable to wear all day. We appreciated how sleek these shoes looked and figured they would be worth at least double what they actually cost — making this a great starter shoe for someone who wants a nice pair without overspending. If there’s one thing we could change, it would be the lack of arch and heel support. But everything else, from the surprisingly comfortable insole to the shiny faux leather, made us want to grab these in a few different colors (six, actually). For someone exploring their fashionable side while staying cost-conscious, this is the pair to snatch up. Sizes: 6.5-15, regular and wide | Colors: 6 | Material: Faux leather, rubber, plastic PHOTO: People / Henry Yung PHOTO: People / Henry Yung PHOTO: People / Henry Yung PHOTO: People / Henry Yung Best Under $100 Clarks Tilden Cap Oxford Shoe PHOTO: Amazon $90 $40 at Amazon $70 at Zappos $100 at QVC Star Qualities Specialty footbed provides great cushioning and minimizes shock Versatile style works with a variety of clothes Sturdy design will last for years Red Flags They run small, so order at least a half size up Many dress shoes with a budget-friendly price tag skimp on comfort and durability, but not this pair from Clarks. These dress shoes scored high across all attributes — especially comfort. They feature an OrthoLite footbed, which provides ample cushioning to minimize shock during walking. They were also significantly more lightweight (and not as stiff) as other dress shoes we tested. We also found these shoes to be solidly built and made to last. We also found that this style of dress shoe was easy to pair with other things from our closets. They complimented a variety of dress pants, including chinos and blue jeans, but are equally suitable for city commuters and those searching for formal event shoes. Overall, these dress shoes maintain exceptional quality given the price: The stitching is tight, the colors are versatile, and the construction is sturdy without being uncomfortable. The one downfall? They run small, so you’ll need to order at least a half size larger than your typical size when purchasing these shoes. Sizes: 7-15 | Colors: 7 | Material: Leather upper People / Daniela Galvez Best Oxfords Ace Marks Cap Toe Oxford PHOTO: Ace Marks View on Acemarks.com Star Qualities They run true to size Comfortable to stand in for long periods of time Waxed shoelaces hold their shape well Red Flags Required a break-in period of four to five wears A classic pair of Oxfords is suitable for a variety of formal styles, from tuxedos to full suits, as seen on the red carpet. These oxfords from Ace Marks are handmade in Italy and feature a handsome cap toe, ultra-soft calfskin leather, and blake-flex construction to ensure flexibility. We like that this pair has waxed shoelaces, which means that they will stay tied for longer — perfect for formal events that you anticipate will run long. The leather soles also provided good traction. It took about four to five normal wears to break these in, which is normal for this type of shoe and material. Still, the heels, toes, tops, and bottoms of our feet felt comfortable after several hours of wear and the material remained breathable and comfortable for extended periods of time. In terms of sizing, these were one of the few dress shoes that were true to size. We didn’t experience any uncomfortable pinching or chafing during wear and its stacked, flat heel didn’t cause any pain throughout the day. Overall, these Oxford dress shoes held up great during testing and exemplified top-notch stitching, construction, comfort, and fit. Sizes: 5-15 | Colors: 5 | Material: Calfskin leather People / Art Silverio Best Oxfords, Cheaper Cole Haan American Classics Montrose Oxfords PHOTO: Cole Haan View on Colehaan.com Star Qualities Comfortable insole needed little to no break-in period High-quality material is tough against typical wear and tear Versatile design is easy to style several ways Red Flags Honestly, no complaints here It’s rare that we don’t have a single critique when it comes to a new product that we’re testing, but alas, it happened with this pair of Cole Haan oxfords. The sleek exterior of the shoe immediately grabbed our attention, and we discovered that the material is as durable as it is sleek when it survived an encounter with puppy teeth without so much as a scratch. The comfortable footbed, which is made from EVA foam and is anatomically molded, made this pair super easy to wear all day long, whether commuting to work or standing for hours at events. Everything from supportive arches to sturdy laces indicates you'll get several years of use out of these. While $190 may sound high, these shoes are worth every penny. In fact, we’d go back for a second pair in another color. Sizes: 7–13 | Colors: 3 | Material: Leather, EVA PHOTO: People / Sarah Naftzger PHOTO: People / Sarah Naftzger PHOTO: People / Sarah Naftzger PHOTO: People / Sarah Naftzger Best Investment Magnanni Corey Oxford Shoe PHOTO: Magnanni View on Magnanni.com Star Qualities High-quality materials that will last Flexible from heel to toe Elongated toe box makes shoe more comfortable Red Flags They require a brief break-in period If you're looking to invest in a comfortable dress shoe that's equal parts modern and sleek, look no further than the Corey Oxford Shoe from Magnanni. The quality of these shoes is undeniable — the leather, soles, and heel look and feel as if a craftsman took great care to make them (spoiler alert: they did, hence the high yet fair price). They also have an elongated toe box for added comfort. Not only are they well-made, but they look good, too — boasting a polished appearance courtesy of a hand-painted finish that elevates any outfit in an instant. Aside from the classic cap toe (which is a wardrobe staple), this pair relies on an all-leather construction to ensure it is lightweight and flexible enough to not cause blistering or chafing. While these needed to be broken in during testing (much like most oxfords on the market), they were fully comfortable by the second wear. Sizes: 7-15 | Colors: 3 | Material: Leather PHOTO: People / Karen Chen PHOTO: People / Karen Chen Best Boots Thursday Boot Co. Cavalier Chelsea Boot PHOTO: Thursday Boot Co. $190 at Amazon View on Thursdayboots.com Star Qualities Easy to slip on and off Made from water-resistant leather and suede Features a non-slip outsole Red Flags We wish they were more cushioned Whether it’s a casual boot (like our favorite Dr. Martens) or a dressy fall boot, you can’t beat the style and function of a taller shoe. The best thing about a Chelsea boot like this pair from Thursday Boots is its sheer versatility: It can be dressed up for a more formal event or down for casual outings, as well as being worn daily if you work in an office setting. One of the first things we noticed when we took these out of the box was the elastic sides, which made them easy slip on and off during testing. These boots ended up molding to our feet nicely and didn't feel too loose or too restricting after the break-in period. However, a bit more cushioning would have made these more comfortable, especially if you will be standing for long periods of time. Though on the pricey side, the boots' well-made construction, comfort, and fit are enough to justify their price. Sizes: 6-16 | Colors: 6 | Material: Full-grain leather, suede (depending on color) People / Daniela Galvez Best Casual Dr. Scholl's Sync Oxford PHOTO: Amazon $85 $60 at Amazon $65 at Walmart $65 at Zappos Star Qualities Comfortable option for long periods of wear Easily mold to your feet; no break-in period Budget-friendly version of the classic style Red Flags The faux leather material isn’t the most durable You can't go wrong with having a classic lace-up Oxford in your arsenal, and if you're on a budget, this pair from Dr. Scholl's is a great option. Dr. Scholl’s sneakers are famous for their comfort, and we’re happy to report that their dress shoes are no different. They provide all-around comfort underneath the toes, at the ball of the foot, and at the heel thanks to a dense foam footbed. Though we’re drawn to this pair for its reasonable price tag and attractive style, its faux leather material may not hold up to standard wear and tear. But given its versatile styling options, ultra-comfy footbed, and attractive appearance, we can see ourselves repurchasing these when the time for a refresh comes around. Sizes: 8-15 | Colors: 9 | Material: Faux leather upper PHOTO: People / Jennifer May PHOTO: People / Jennifer May PHOTO: People / Jennifer May Best for All-Day Wear Stacy Adams Dickinson Cap-Toe Oxford PHOTO: Amazon $110 $55 at Amazon $80 at Zappos $115 at Macy's Star Qualities Comfortable enough for long periods of wear Molded easily to our feet, eliminating a break-in period Budget-friendly option for a high-end look Red Flags You’ll need to wear thicker socks to avoid heel chafing Dress shoes don't have to be uncomfortable, as evidenced by the Stacy Adams Dickinson Cap Toe Oxford. This pair was comfortable right out of the box, with enough flexibility that we could put them on without a shoehorn. The sole is more plush than the other dress shoes we tried, making these ideal to wear all day long. While our feet weren't sore after wearing this pair, there was some slight chafing in the back of the heel at the top seam (slightly thicker socks would later fix this). Most dress shoes have a reputation for being tight in the toes, but this pair has an elongated toe box that creates space for added comfort. There’s also padding in the sole and heel that offers additional anatomical support. This pair scored more points with its faux tanned leather and eyelet perforations — making the shoes look more expensive than they are. These shoes check all the boxes: comfortable, dressy enough for special occasions, and reasonably priced. Sizes: 7-16 | Colors: 5 | Material: 100% leather PHOTO: People / Alessandra Amodio PHOTO: People / Alessandra Amodio PHOTO: People / Alessandra Amodio The 15 Best Slip-On Shoes for Women, According to Testers, Stylists, and a Podiatrist Best Slip-On Mephisto Edlef Slip-On PHOTO: Amazon $319 at Amazon $319 at Nordstrom $319 at Zappos Star Qualities Plush footbed was exceptionally comfortable Durable rubber sole for offered flexibility and traction Includes elastic gore inserts for stretch Red Flags Could cause chafing if you don't wear them with the right socks When it comes to the Mephisto Edlef Slip-Ons, comfort is king. Though they look like an elevated everyday slip-on, these were as plush as slippers when we slid into them and required no break-in period. The footbed is made with a removable Cool-Air footbed for enhanced comfort — a feature that made all-day wear possible — and the soles include a shock-absorbing heel. Plus, the material is top tier: supple to the touch and holds its shape without being too rigid (we didn’t even need a shoehorn to get in and out of these). These molded extremely well to the shape of our feet and they come with elastic gore inserts, which helps stretch the shoe for wearers with wider feet. But because this foot-conforming design is like a second layer of skin, it’s important to wear the right kind of socks to prevent chafing — we’d suggest ankle socks for the best experience. Sizes: 7-13 | Colors: 3 | Material: Leather upper and lining/rubber sole PHOTO: People / Hang Pham PHOTO: People / Hang Pham Others We Tried Clarks Bushacre 2 Chukka Boot: This dressy boot had almost everything we were looking for — an attractive design, a mildly supportive footbed, and decently high-quality materials. Its low price is an incredible value for its high-end look, though we wouldn’t reach for these on long walking days because the footbed isn't as comfortable as others we tried. These are great for special occasions when you won’t be wearing them for too long and don’t want to spend more than $100. What to Know About Dress Shoes Comfort Comfort is important for all types of shoes, but particularly for dress shoes that you'll be wearing to a special event or work. According to Spielfogel, arch support is critical. "Many people have foot conditions such as flat feet, plantar fasciitis, bunions, and hammertoes, so it's very important to make sure there is appropriate arch support when wearing shoes so that you don’t aggravate these conditions," he says. Patrick Kenger, the personal stylist at Pivot Image Consultancy, says that the best time to try on new potential dress shoes is at the end of the day. "As you walk and go about your day, your feet will swell and expand a bit, so you want to make sure your [new] shoe accommodates your foot at all times." Ultimately, you'll know you have an ill-fitting shoe if your heel slips out the back, there's pinching at the toe box when walking, or it causes blisters, says Kenger. We felt like the Cole Haan Original Grand Wingtip Derby provided comfort, support, and style, making it our top overall choice. Price Dress shoes can be pricey, but they're a wardrobe staple that may be worth splurging on — especially for men who are just building their wardrobe with a clothing subscription box. "Leather isn't cheap, to begin with — couple that with the fact that you're on your feet all day and your shoes can impact your posture and comfort level, this is not an area you cheap out," says Kenger. At a minimum, you can expect good dress shoes to cost $100, however, the Dr. Scholl's Men's Oxford is a great option if you want a comfortable shoe on a budget. "There's a lot that goes into making a dress shoe, and there are many different material types and pieces to the puzzle," he adds. If you're ready to invest in a dress shoe, Kenger recommends seeking out brands that specialize in only making shoes to ensure quality and longevity. And, to prolong the life of your dress shoes, don't underestimate the power of a shoe tree. Style Dress shoes tend to tip on the fancier end of the scale, but there are still more casual options out there. While oxfords are typically reserved for more formal occasions (especially if you wear them in black), a loafer, like the Clarks Men's Tilden Cap Oxford Shoe, is on the more casual side and is best paired with a suit that has a bit more flair (such as one with a pattern), says Kenger. Loafers can also provide more comfort and are ideal for men who favor slip-on shoes in general. "Derby shoes are also a bit more casual than the Oxford and a good go-to for business casual looks," notes Kenger. Finally, if you're looking for a dress shoe with a similar formality level and function as a loafer but adds an extra touch to your look, go for double monk strap dress shoes. People / Danielle Yersin Behind the Scenes Our PEOPLE Tested team tried out 22 pairs of dress shoes. For each pair of shoes, we looked at comfort, fit, quality, and value. Eventually, we narrowed it down to 10 of the best styles. To determine this, we checked in three separate times to record our thoughts on first impressions, after two hours of wear, and following a full day’s-worth of wear. Initial Impression: To get an initial impression, we wore the dress shoes right out of the box for 30 minutes and walked on a hard, flat surface. We looked at how flexible shoes were and if they molded to our feet well. We also considered whether it caused rubbing or chafing anywhere on our feet and sizing accuracy. Two-Hour Wear: For the two-hour wear, we wore the shoes consistently for a longer period of two to three hours of intermittent walking, movement, and standing (for instance, working, running errands, sightseeing, or dancing). We noted how comfortable the shoes were, their traction on various surfaces, their breathability, fit, and how well they would last during a longer event.Full-Day Wear: Finally, for the third wear test, we wore the dress shoes for a full day (at least eight hours). We inferred whether or not they were broken in, how well the tread held up, how comfortable and supported the soles felt and the level of quality of the construction and design.Evaluation: During all three test phases, we considered whether the shoes were immediately comfortable or had a break-in period, whether they had supportive soles, and how comfortable they were during short-term and long-term wear. We also took into account fit — including whether the shoes fit as expected, given shoe size and shape, and whether our feet felt restricted or loose within the shoe. When looking at the price of each dress shoe, we noted if we could defend the pricing for higher-end or lower-priced items and if we felt that the quality was higher than expected, given the cost. In the end, ten dress shoes passed each test, with each one having standout features related to comfort, durability, and material. Why Trust PEOPLE? Michelle Rostamian is a beauty, wellness, and lifestyle writer with nearly 10 years of experience in the beauty industry and bylines at PEOPLE, Byrdie, Real Simple, InStyle, and more. She began her career in the beauty industry as a publicist and content writer representing makeup and skincare brands as well as industry professionals. She formerly was a social media marketer. Michelle graduated from the University of California, Los Angeles with a B.A. in Communications. For this story, she evaluated the insights from our testers, who tried out 17 of the best pairs of men's dress shoes on the market. She compared their feedback on the fit, comfort, quality, and value of each pair of shoes, and ultimately narrowed the list down to those with the highest scores. She also sought expertise from William D. Spielfogel, a New York-based podiatrist, and Patrick Kenger, a professional personal stylist at Pivot Image Consultancy. This story was later updated by staff shopping writer Alyssa Brascia, who used the insights provided after new tests in 2024 to see which new styles were winners. Meet Our Experts William D. Spielfogel is a New York-based podiatrist and medical advisor to The Good Feet Store. Patrick Kenger is a professional personal stylist at Pivot Image Consultancy. What Is PEOPLE Tested? We created the PEOPLE Tested seal of approval to help you find the very best products for your life. We use our unique methodology to test products in three labs across the country and with our network of home testers to determine their effectiveness, durability, ease of use, and so much more. Based on the results, we rate and recommend products so you can find the right one for your needs. But we don’t stop there: We also regularly re-review the categories in which we’ve awarded the PEOPLE Tested seal of approval — because the best product of today might not be the best of tomorrow. And by the way, companies can never buy our recommendation: Their products must earn it, fair and square. In short, PEOPLE Tested provides recommendations you can trust — every day, every purchase. The 13 Best Flip-Flops for Men, Tested by Real People