As the country slowly starts to reopen, some sense of daily life and normalcy is sure to follow. When it does, we’ll all have to ditch the sweats, hang up the comfy hoodies, get a much-needed haircut (hopefully) and try to right the ship. While some are thriving in their work-from-home atmosphere, others are excited to dress up and look their best again.
Just as every house needs a foundation, a solid outfit stands upon a good pair of dress shoes. The best men’s dress shoes are versatile, comfortable and durable. They’re items worth investing in, especially when you find a pair you like. But the truth is, you might end up buying multiple pairs. That’s because there are a lot of different kinds of dress shoes, and they can suit different settings. Plus, there are a variety of color options, with black being the most formal and brown being more versatile for different suit colors.
Men’s Dress Shoe Styles, Explained
There are a lot of different kinds of men’s dress shoes, and they vary considerably in terms of style and formality. Even in today’s dressed-down environment, it’s still important to be mindful of which styles are appropriate for which setting. That’s why we’ve broken down some of the most common styles of dress shoes, and many of these styles can be found on our list.
- Oxford: Arguably the most traditional style, Oxford shoes are characterized by “closed lacing” with eyelets under the vamp instead of on top, creating a more streamlined and formal look.
- How to wear it: Oxfords look best with a traditional suit and are too formal for jeans.
- Derby: Derby dress shoes are similar to Oxfords, but they have “open lacing,” with eyelets on top of the shoe.
- How to wear it: Derbies are slightly more casual than Oxfords, and many derbies are versatile enough for suits as well as jeans or chinos.
- Wingtip: A wingtip can be an Oxford, a derby, or even a boot. They’re characterized by stitching that’s shaped like a wing, and they often have an ornate perforated medallion design on the toe. The perforation itself is called broguing.
- How to wear it: Wingtips are more casual than plain-toe Oxfords, and some wingtips can be worn with more casual pieces.
- Loafers: Loafers are among the more casual shoe styles that are still commonly worn with suits. They’re laceless shoes that are meant to be slipped on. They come in various styles including penny and horse bit.
- How to wear it: Loafers are inherently more casual, but they still look great with a suit. More casual penny loafers can also be worn with jeans, too.
- Tuxedo shoes: Tuxedo shoes are often made from patent leather, which is leather that’s been coated to have a high gloss finish. They come in lace-up or loafer styles. Another kind of tuxedo shoe is the velvet Venetian slipper.
- How to wear it: Patent leather tuxedo shoes should pretty much only be worn with a tuxedo.
- Dress boots: Dress boots are short boots with a more pointed silhouette, as opposed to taller, round-toe work boots. They come in lace-up, Chelsea and wingtip styles.
- How to wear it: Dress boots look great with a suit or jeans. If you’re wearing them with a suit, make sure the pants drape nicely over the shaft of the boots and the boots don’t create lumps under the pants.
While normally finding the perfect dress shoe takes a little time, we’ve compiled a list of the best dress shoes for men that are great in nearly all types of settings for nearly every foot.
1. Ace Marks Luke Wingtip
The first priority dress shoe that every man needs to have in his closet is a brown wingtip oxford shoe. Now, Cole Haan used to crush the competition with their “Air Giraldo,” but after Nike sold Cole Haan in 2012, they discontinued the style not too long after, leaving guys in search of the next big thing. For this writer, the Ace Marks Luke Wingtip is the ultimate solution. Born right at the time of the Cole Haan sale, Ace Marks offers affordable luxuries — but, really.
This shoe is hand-made in Italy from supple, yet, durable leather with a full calf-skin lining from heel to toe. The shoes are incredibly flexible and don’t take much time for a foot to warm up to the shape. What I most appreciate about this shoe is the generous amount of room in their D (medium) width. Even though they’re available in an E (wide) width, the D width won’t make you feel claustrophobic upon the first wear. Style these with any kind of business or dress-casual attire. They look just as good with a suit and tie as they do with cuffed up chinos and a camp shirt.
2. Church’s Dubai Polished-Leather Dress Shoes
Legendary English shoemaker Church’s has been in the business since 1873, and while a lot has changed since then (the brand is now owned by Prada), these shoes are still made in the UK. These cap-toe oxford shoes are a more formal pick that works well with a navy suit, but the brown color also works well with a more casual piece like a tan or light beige suit. They’re Goodyear-welted, meaning the soles can be replaced. You can also get them in black.
3. Bruno Magli Maioco Leather Oxford
BEST BLACK CAP TOE
I’ve known men who have worn the Maioco for 10 years straight. Why? Because it works for every foot and body type. The Bruno Magli Maioco is your classic black cap toe shoe for men who like a sleek, euro-style look. Sure, every brand makes their version of a black cap toe shoe, but the toe shape of this style is what sets it apart from the rest. Bruno designed the Maioco with the perfect almond toe shape, so it’s not too long and pointy nor too round and snub. This classic style is handmade in Italy with a Nappa leather upper, a full leather sole and a rubber heel for extra grip. Though they last for years, the Blake-stitched sole can be re-soled by your local cobbler after it wears down. Wear this with your suits or with a pair of black or dark wash jeans and your choice of white t-shirt.
4. Grenson Dylan Burnished-Leather Wingtip Brogues
Grenson is a British shoemaker with a serious pedigree, and the brand dates back to the 1800s. But they’re also brand not without a sense of fun. From chunky-soled hikers to sleek sneakers, Grenson dabbles in all sorts of footwear styles. Of course, they also have the basics nailed down, like these classic wingtip brogues. They have rubber-trimmed soles for added traction.
5. Allen Edmonds Crosby Street Split-toe Blucher
When it comes to American shoe brands, Allen Edmonds is undoubtedly one of the most iconic. Founded in 1922, the brand still offers American-made shoes. These stylish derbies are made in Allen Edmonds’ hometown of Wisconsin, using imported leather. These shoes are a great option if you’re looking for a proper dress shoe that still stands out from the pack. These shoes have a split-toe design and apron-stitching on the vamp. These shoes are discounted, so you’ll need to act fast, as some sizes are no longer available.
ON SALE NOW
6. Trickers Robert Full-Grain Leather Derby Shoes
THE OG BRITISH FOOTWEAR BRAND
Founded in 1829, Trickers is one of the oldest British shoemakers still in operation, beating out John Lobb, Grenson, and Church’s by 20, 37 an 44 years, respectively (but who’s counting?). But these derby shoes are surprisingly sleek and modern, with a slightly pebbled texture and a simple, unadorned upper. These shoes are made in the UK with full-grain leather, and they have rubber on the heel for added grip.
7. Johnston and Murphy XC Flex Longwing Derby
Johnston and Murphy is one of the best brands for affordable footwear, and this derby is a versatile option if you’re looking for something that you could wear with a suit or a pair of selvedge jeans. Admittedly, they’re not the most traditional shoes, but that’s part of what makes them cool. The thick, textured sole not only makes them better suited for walking on less-than-perfectly paved ground, but it also makes them a more stylish shoe, especially to wear with the looser kinds of silhouettes that are in style now.
8. Alden Cordovan Plain Toe Blucher
NEW ENGLAND ICONS
This plain toe blucher is a simple, streamlined shoe that would look great with a suit. But because of the slightly more casual derby-style construction of this shoe, it’s also an option that can suit more casual outfits. Alden was founded in 1884 and is one of (if not the) most respected American shoemakers still in business today. Yes, these shoes are expensive. But with premium cordovan leather construction, a Goodyear storm welt, and made-in-America manufacturing, these shoes are a worthwhile investment.
9. GH Bass Larson Weejuns
Jeans, chinos, suits and even shorts. Loafers are truly the shoes that can do it all, and Bass is the brand that can best lay claim to the creation of the slip-on penny loafer. The Bass Weejun has all the hallmarks of a classic penny loafer, including a leather panel across the top of the shoe with a small window (where people would store lucky pennies), distinctive “beef roll” stitching on the edges of the shoes, and mocassin stitching across the vamp. They’re an old-school shoe that’s back in style in a big way, and while they’re a little more casual than the average dress shoe (or even the average loafer) don’t be afraid to wear these with your favorite suits.
10. Magnanni Dorio Venetian Loafer
BEST FOR TUXEDOS
There are two common tracks you can take when choosing shoes for eveningwear. You can go for high-shine, patent leather. Or, there’s the laid-back but still-elegant velvet shoe. This Venetian slip-on loafer from Magnanni is the latter, and it embodies the formal yet somewhat louche look of a velvet shoe. It’s a great option for anyone suiting up in a tux who wants to make a fashion-forward statement without actually breaking any of the rules of formalwear. It’s available in black or blue velvet.
11. R.M. Williams Comfort Craftsman Chelsea Boots
BEST DRESS BOOTS
Looking to inject a little outback style into your tailored look? Go for R.M. Williams, a brand so Australian it enlisted Hugh Jackman as its global brand ambassador. These shoes straddle the line between formal and rugged perfectly — the Chelsea boot has practical pull tabs, a high heel, and a cowboy-inspired shape. But the refined leather and streamlined shape make it a great option to wear with tailoring.
12. Cole Haan ZeroGrand Stitchlite Oxford
BEST FOR SUMMER
After Nike sold Cole Haan, they needed a new focal point. One thing you may have noticed is, within the last decade, there’s been this style tsunami (more than a wave) of meshing aspects of business attire with aspects of casual attire. When done correctly, outfits look appropriate for both going to church or a looking stylish court-side at a basketball game. We call this “smart-casual style,” and it’s here to stay. Where does Cole Haan fit into this? Nike-made Cole Haan had previously designed the Lunargrand shoe, which combined a dress shoe upper with the Nike “Lunar” sneaker sole. In 2014, Cole Haan decided to run with this sneaker idea (pun intended) and developed the ZeroGrand — a new take on the dress shoe upper and a sneaker bottom, except this time, with lateral cuts for complete flexibility. It was a huge success and completely redefined wear-to-work shoes. The Stitchlite Oxford is an iteration of the ZeroGrand sole technology with Cole Haan’s signature woven upper material. These shoes are breathable, flexible and comfortable and are the ultimate summer dress-casual shoe. Grab the white and try them with a summer suit.
Read more: The Best White Sneakers for Men
13. Beckett Simonon Dowler Boot
BEST BANG FOR YOUR BUCK
The Beckett Simonon Dowler Boot is kind of like New Orleans Saints backup quarterback, Taysom Hill — both can make huge plays no matter how you use them. While Hill can score both from the backfield and the slot, the Dowler boot can be worn with anything from the most polished suit to the most distressed denim. Boots and suits are great together, and if you’ve never tried it, you must.
The Dowler Boot is constructed from a whole-grain, Argentinian leather that shines and cleans like no other with a Blake-stitched sole for easy future repairs. The leather is sturdy but soft enough to support your ankles comfortably and develops a gorgeous patina the more you wear it. All of Beckett Simonon’s prices are lower because they’ve cut out all middlemen. For $229, this luxurious-feeling boot is an absolute robbery. The Dowler Boot in Bordeaux, in my personal opinion, is the nicest looking and can be worn with your favorite dark grey or navy suit or simply with any fun suit separates. For casual looks, put on a pair of jeans and run wild.
14. Gucci Bit Loafer
THE ULTIMATE LOAFER
The Gucci Bit Loafer comes with decades of legendary design, top quality materials and a luxury price tag, but I’ll be damned if this isn’t the perfect loafer for both dressing up and dressing down. The ideal loafer has a balanced silhouette, can be worn all day and adapts to the changes of your lifestyle. The Gucci Bit Loafer’s vamp lies perfectly centered on your foot. The slim leather sole creates a more refined look. And the horse bit, no stranger in the loafer world, adds a shine that ties the whole outfit together. To wear the Gucci Bit Loafer like a boss, put on a slim suit with a tapered leg and a hemline above the ankle. For a dressed-up daytime look, try wearing this with a pair of flat-front shorts, a dress shirt and an unlined, lightweight blazer.
15. Stacy Adams Donovan Slip-On
THE ELEVATED LOAFER
If you’re somebody who has a decent shoe collection, this is a style for you to consider. The tassel loafer, popularized less than a century ago by American brand, Alden, is a fairly new shoe style among dress shoes. In the world of slip-on shoes, sometimes things can get a bit boring. One way to spice things up is to add the tassel. It’s not a shoe to wear all the time, because it does leave a lasting impression, but it is something to pull out when you want to make a statement. The Donovan tassel loafer from Stacy Adams is a great, affordable option for warm weather months and lighter fabric outfits. For example, this type of loafer goes perfectly with tan linen suits or anything chambray. This also looks great with one of these slim chinos and a polo tucked in. There’s a certain throwback aesthetic to the tassel loafer and we’re very much here for it.
16. Allen Edmonds Park Avenue
BEST SHADE OF BROWN/BEST OVERALL FIT
The best brown dress shoes for men should match with any outfit worn. It shouldn’t be too dark, like black, nor too light, like tan, but the exact color of milk chocolate. Allen Edmonds, a coastal Wisconsin brand who has made some of America’s best dress shoes for men since 1922, knows a few things about illustrious color. The Allen Edmonds Park Avenue oxford is a staple for men’s shoes and comes in five standard colors as well as fun seasonal colors, including multiple shades of brown. Their “coffee” color is the perfect medium brown. It looks great paired with any shade of grey, blue, tan and more. Depending on the outfit, it even looks good with cuffed black chinos.
Like the wide range of colors, Allen Edmonds also manufactures a wide range of sizes. This shoe is available from a men’s size five to 16 and widths ranging from 4A (extra narrow) to EEE (extra wide). If you’re looking for a basic men’s dress shoe, this is a great pair to start with. They’re insanely durable, great for all-day wear and are sure to last for years.
17. Florsheim Tux Plain Toe Derby
BEST FOR FORMALWEAR
Sometimes, tuxedos or tuxedo-equivalent suits are a must. These occasions are best suited (pun intended) for patent leather shoes. Now, if you’re somebody like The Masked Singer host, Nick Cannon, you’re dressing up all the time and should opt for something swanky, maybe from Christian Louboutin to make a statement. For those of us who are not Nick Cannon, you probably only attend a formal event once or twice a year and just need something comfortable, nice looking and affordable. This patent leather derby from Florsheim ticks all the formalwear boxes and has a 4.8-star review from customers on Nordstrom. The most important factor when styling a formal shoe like this is how your pants break at the bottom. Plain toe patent leather shoes work for most guys because they look longer under the break of a pant leg whereas cap toe shoes can sometimes look short. For a cropped tuxedo pant, a smoking slipper might do well also.
18. Taft Prince Double Monk Strap
THE HEAD TURNER
Once your basic shoe styles are covered, you’re going to want something fresh that’s not a slip-on or an oxford. A monk strap shoe is the next logical shoe for your collection. Taft, since 2013, has created a steady and loyal following on social media that obsesses over their attention to quality, innovative design and excellent fit. This is a brand you need to know. Spanish-made Taft shoes are designed for dapper dudes who like that sweet spot between the trendy and traditional. The Prince double monk strap shoe from Taft uses a criss-cross strap mechanism, which is both atypical and sleek as hell. Its French calfskin leather upper and Goodyear welt sole ensure longevity and durability while the leather lining and cushioned insole provide you with all-day comfort. These shoes fit great right out of the box. Wear these with your favorite lightweight suit or with a pair of cuffed-up, dark-wash jeans and your go-to blazer.
19. Common Projects Low-Top Derby Shoes
BEST TRENDY DRESS SHOE
We love Common Projects classic Achilles sneakers, but don’t let those overshadow their other styles. Common Projects embodies the pulse of what’s on-trend, making some of the best dress shoes for men who like to live in the right now. One trend that’s held strong for the last few years is the wedge sole dress shoe, like Common Projects’ Low-Top Derby. An almond toe, this derby style shoe is a sure fit for all body types and outfit styles while giving you a slight height boost. They look as good with a straight fit pant as they do with a skinny cropped trouser, especially in monochromatic colors.