If you purchase an independently reviewed product or service through a link on our website, SPY.com may receive an affiliate commission.
With the world slowly reopening, a sense of returning to daily life and normalcy won’t be far behind. We’ll have to sideline the sweats, hang up the comfy hoodies, get a much-needed haircut (hopefully) and try to right the ship. While some thrive 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 various color options, with black being the most formal and brown being more versatile for different suit colors.
Men’s Dress Shoe Styles, Explained
There’s a wide range 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 types of dress shoes, and many of them 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 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 you can wear some wingtips with more casual pieces.
- Loafers: Loafers are among the more casual shoe styles still commonly worn with suits. They’re laceless shoes that are meant to be slipped on. They come in various types, including penny and horse bit.
- How to wear it: Loafers are inherently more casual, but they still look fantastic with a suit. You can also wear more casual penny loafers with jeans too.
- Tuxedo shoes: Tuxedo shoes are often made from patent leather, which has 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 than 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 boots’ shaft, and the boots don’t create lumps under the pants.
While usually 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 almost every foot.
1. Ace Marks Luke Wingtip
The priority dress shoe that every man needs to have in his closet is a brown wingtip Oxford shoe. This shoe is handmade in Italy from supple, durable leather with a full calfskin 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 we appreciate most about this shoe is the generous amount of room in its 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 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 Cap Toe Oxford
Legendary English shoemaker Church’s has been in the business since 1873, and while a lot has changed since then (Prada now owns the brand), 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 You can replace the soles. 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 its version of a black cap toe shoe, but this style’s toe shape 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, an entire 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 a white t-shirt.
4. Cole Haan Modern Classics Wingtip Oxford
This is about as classic of a Cole Haan silhouette as there is. The brand is classy, defining dress shoes, typically with more comfortable insoles. These shoes shed the old stereotype of wholly uncomfortable heels, offering long-lasting comfort when your calendar calls for all-day dress attire. While not a completely traditional brogue, the Modern Classics Wingtip Oxford is a modern take on it.
5. Bally Apron-Toe Leather Derby
This is Bally’s classic, sleek take on the derby. Of course, there’s always the designer route with men’s dress shoes. The nice thing about an apron-toe is that there isn’t much room to get crazy with the design (as some higher-end brands are wanton to do), and Bally’s offering is a prime example of high-grade materials in a timeless look. The added bonus of this coffee colorway is that it can be formal enough when needed and will also dress down quite nicely.
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 and 44 years, respectively (but who’s counting?). In any case, these derby shoes are surprisingly sleek and modern, with a slightly pebbled texture and a simple, unadorned upper. They’re made in the UK with full-grain leather, and they have rubber on the heel for added grip.
7. Johnston & Murphy XC Flex Longwing Derby
Johnston & 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 selvage jeans. Admittedly, they’re not the most traditional shoes, but that’s part of what makes them great. 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 looks great with a suit. However, this shoe’s slightly more casual derby-style construction also makes it an option for 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. G.H. Bass Originals Logan Flat Strap Weejuns
Jeans, chinos, suits, shorts — loafers are truly the shoes that can do it all, and Bass is the brand that can best lay claim to creating the slip-on penny loafer. The Logan Flat Strap 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 moccasin 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 Dante Patent Leather Derby
BEST FOR TUXEDOS
A good tux shoe calls for shiny patent leather, and the Dante is a great choice. There are two typical 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 lace-up derby from Magnanni is the former, and it embodies the formal look we normally associate with a tuxedo. It’s an excellent option for anyone suiting up in a tux who wants to stick to the most classic definition of evening formalwear.
11. R.M. Williams Comfort Craftsman Chelsea Boots
BEST DRESS BOOTS
Are you 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. Ideally, these shoes straddle the line between formal and rugged — the Chelsea boot has practical pull tabs, a high heel, and a cowboy-inspired shape. But the refined leather and streamlined silhouette make it a great option to wear with tailoring.
12. Common Projects Original Achilles Sneaker
BEST FOR SUMMER
One thing you may have noticed is, within the last decade, there’s been a significant shift to meshing aspects of business attire with elements of casual clothing. When done correctly, outfits look appropriate for both going to church or looking stylish court-side at a basketball game. We call this “smart-casual style,” and it’s here to stay. Where does Common Projects fit into this? You could probably credit the launch of sneakers with suits to the brand that still makes a shoe worth the envy. This shoe makes any suit look cooler and any casual outfit more refined. Basically, if a sneaker costs this much, it better look good with everything. Good for us all; this one does.
Read more: The Best White Sneakers for Men
13. Beckett Simonon Dowler Boot
BEST BANG FOR YOUR BUCK
The Beckett Simonon Dowler Boot is like New Orleans Saints backup quarterback Taysom Hill — both can make huge plays no matter how you use them. While Hill can score from the backfield and the slot, you can wear the Dowler boot 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. Beckett Simonon’s prices are lower because they’ve cut out all middlemen. For $239, 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 Jordaan Bit Loafer
THE ULTIMATE LOAFER
The Gucci Jordaan 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 your lifestyle changes. 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. Johnston & Murphy Hayes Tassel Loafer
THE TASSLE 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 reasonably new shoe style among dress shoes. 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 sure throwback aesthetic to the tassel loafer, and we’re very much here for it.
16. Allen Edmonds St. Johns Double Monk Strap
BEST BROWN DRESS SHOES WITH BEST OVERALL FIT
Enjoy extra flexibility and this gorgeous hue with this double monk strap shoe. The best brown dress shoes for men should match with any outfit worn. It shouldn’t be too dark, like black, nor too light, but somewhere in the middle. Allen Edmonds, a coastal Wisconsin brand that has made some of America’s best dress shoes for men since 1922, knows a few things about illustrious color. The Allen Edmonds St. Johns Double Monk Strap offers that extra bit of flexibility from the adjustable strap and comes in three standard colors. 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 seven to 14 and widths ranging from B (narrow) to EEE (extra wide). If you’re looking for an essential 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. Astorflex Greenflex Chukka
BEST DRESS CHUKKA
If you’re a short guy, boots can look a little … strange on legs with a sub-28 inch inseam. A styling trick we love is opting for a dressier chukka instead of a boot, which gives you that higher-top without the height of a full boot. Astorflex is an Italian brand that prides itself on using less harmful practices (when tanning leather, for example) and has a natural rubber sole for extra comfort on long days. Plus, these are the type of shoes that will get better with age.
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. This crisscross double monk strap is the next logical choice. 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. Its French calfskin leather upper and Goodyear welt sole ensure longevity and durability, while the leather lining and cushioned insole provides you with all-day comfort. These shoes are a cleaner look to focus on the crisscrossing of the straps, and they 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. Blundstone BL1900 Dress Ankle Chelsea Boot
Blundstones are an ideal way to blur the line between casual and dress. They’re durable, hardy and seem to always be a go-to pair for just about any boot need. This dressier option is a sly way to stay formal on days when the weather is inclement or you know you’re headed for a muddy field. The contour is excellent, the fit is everything you’d expect, and they look even better with a thin coat of oil or weatherproofing wax. This boot is a great alternative to round out your dress shoe lineup.