Trendy to Traditional: The Best Men’s Dress Shoes Right Now and How to Find Your Perfect Pair

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, as they can affect your mood, productivity and physical health in the long run.

Traditionally speaking, there are three colors and four major categories that make up “the basics” of what every man needs. Black, tan and chocolate brown are three of the most versatile colors for shoes without any limitations from the season or occasion. Lace-ups, slip-ons, straps and boots are the four primary dress shoe categories.

Despite popular regional belief, there are some styles guys wear as dress shoes that should not be worn for such occasions and reported to the fashion police immediately. These styles include, but are not limited to dock/boat shoes, driving moccasins and anything from Merrell (no offense to the brand, of course).


How to Spot the Best Men’s Dress Shoes

When shopping for a new pair of dress shoes, there’s a list of things to consider to ensure you buy the right product for your situation.

  • Cost – What’s your budget? Don’t be afraid to invest in a good pair of shoes, especially if you know they’ll fit. Depending on what you’re looking for, it is not unreasonable to spend in the ballpark of $250-$400 for a quality shoe that both looks great and will last for decades. Note: Designer prices don’t always mean better quality.
  • Occasion – Are these shoes for work? If so, what is the dress code? Is it a suit and tie kind of deal or do you have flexibility? Are you going to a wedding, a gala or a black-tie event?
  • Outfit – Do you wear suits throughout the week? Do you want a shoe that can be worn casually as well? Slim, straight or relaxed pants? What colors do you like to wear normally?
  • Size – Do you have an under- or over-sized foot? Do you have a narrow or wide foot? Do you want your feet to appear larger or smaller? Would you like a little height boost?
  • Season – Do you need something breathable? Do you need something water-resistant? Is a boot appropriate?
  • Location – Does it rain or snow a lot? Do you walk over cobblestones or other hard surfaces in your area? Would a rubber sole benefit you?
  • Foot Health – Do you deal with bunions, arthritis or plantar fasciitis? Do you need a hard or soft insole?

Wherever you land after asking yourself these questions, there’s a shoe that’s perfect for your foot. It’s real — you can count on that. While normally finding that shoe takes a little time, we’ve compiled a list of 10 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. Cole Haan ZeroGrand Stitchlite Oxford


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.


3. Bruno Magli Maioco Leather Oxford


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. Beckett Simonon Dowler Boot


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.


5. Gucci Bit 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.


6. Stacy Adams Donovan Slip-On


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.


7. Allen Edmonds Park Avenue


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.


8. Florsheim Tux Plain Toe Derby


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.


9. Taft Prince Double Monk Strap


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.


10. Common Projects Low-Top Derby Shoes


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.


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