Oxfords, Derby’s, Monk Straps, Chelsea’s and Chukka’s. What?! As a man, it’s imperative to maintain a well-dressed appearance, but not everyone knows what dress shoes pair best with each occasion. From business professional to casual to weekend wear, knowing what style of shoe fits the dress code for the outing makes all the difference in conveying your knowledge and self-awareness to the outside world. There’s a lot of shoes out there for those looking to enter the market, and if you desire to perfect the art of discerning shoe styles that, at least to the untrained eye, appear somewhat similar in style and taste, we’re here to help.
That’s why we’ve gotten together to pull several of the essential styles to complement any man’s wardrobe. And don’t worry, we’ve included a few classic examples of each. So, let us facilitate this first step in upping your gentleman’s game, who knows, you may even impress a few people along the way. Dive into our list of the 27 best dress shoes for men below.
Commonly referred to as one of the most elegant types of men’s shoes, the Oxford was first made popular by the students of Oxford University around 1825. Before then, men’s footwear was dominated by boots. Soon, these lower cut shoes became the norm among gentlemen of the time.
The biggest determining factor of the Oxford is the lacing system. The Oxford features a closed lacing system, as opposed to an open lacing system (more on that later), meaning the leather upper is stitched to the rest of the shoe, unlike its Derby counterpart. Other characteristics include low heels and exposed ankles.
Hugo Boss Eveprim Cross Grain
Crafted in Italy, these Oxford shoes were built with the same quality and precision as the Hugo Boss’ renowned tailoring. They’re undoubtedly elegant with a modern feel thanks to its cross grain leather construction.
Johnston & Murphy Melton
These imported leather beauties feature a leather sole and a heel measurement of 1.25″. Also, its goodyear welt construction allows the leather to mold to your foot shape, increasing comfort and facilitating a custom fit.
Grenson’s uncompromising commitment to exquisite style and quality are made apparent in these Oxford shoes. Featuring a genuine leather upper, brogue pattern throughout, and overall leather lining, these imported shoes are covered in class.
The derby, similar to the Oxford, is defined once again by its lacing system. While the Oxford features a closed lacing system, the derby hosts an open lacing system in the form of two quarters that are sewn onto the vamp.
The roots of the shoe aren’t entirely clear. Some trace it back to the 14 Earl of Derby, who had oversized feet and requested his cobbler create the open lace style to help him fit into his shoes. Whatever the case, many attest to the comfort of the derby shoe from the open lacing system, and similar to the Oxford, they suit just about any formal occasion.
OSF34 Tracker Shoe
Manufactured in the UK out of 100 percent leather, the tracker shoe combines the best of classic and contemporary shoe design. Its leather upper pairs quite well with the robber sole, giving the shoe a surprising dose of attitude.
H by Hudson Hadstone Canvas
This classic style shoe strives to innovate and push traditional boundaries while adhering to the style’s roots. The “H” hosts a canvas upgrade from previous designs, waxed contrast laces, and a full leather sock liner providing comfort and style.
PS by Paul Smith
Made in Portugal and handcrafted from calfskin leather, these derby shoes feature a cap-top design, leather sock liner, and contrast waxed laces. Clearly a nod to excellence, these beautiful shoes also host branded back seams and a leather sole.
Here’s where we find comfort over fashion. While they certainly aren’t the most elaborate looking shoes, at least when compared to others in this list, they serve an important purpose: driving assistance. That’s because they’re typically lightweight and feature grippy soles with traction extending up the back of the heel.
The extra grip is meant to provide stability and control while working the pedals of a standard (manual) transmission without compromising comfort on longer drives. What’s also great about drivers is that, chosen correctly, they’re great summertime slip-ons that are both breathable and light.
Tod’s Gommino Leather Driving Shoes
You know a pair of shoes will exhibit quality when they undergo a 100 step process during construction. Each meticulously crafted black leather driving shoe adds elegance to any weekend getup boasting both durability and comfort.
Cole Haan Howland Penny
You’d be hard-pressed to find a more classic driving shoe than the Howland Penny. Comprised of a calfskin upper, contrast stitching and signature hardware detail at the heel, you’ll be cruising through the rolling hills of the UK in your Aston Martin in no time.
1901 Bermuda Driving Shoe
A driving shoe with ‘summer’ written all over it, each Bermuda is fashioned from soft, nubuck leather making this casual driving shoe a must have for everyone’s favorite season. Each pair also features shoe-inspired lacing at the topline, adding to its already handsome look.
Perhaps one of the most misunderstood shoes around, Brogues come from the process of broguing, or the ornamenting of shoes with heavy perforations or picking. Therefore, expounding upon the essence of the confusion, it stands that any shoe with perforations is considered a brogue, even if it fits the derby or oxford style.
The origin comes from Scotland and Ireland as a shoe suitable for wear while working in the outdoors. Originally, the purpose of the perforations in the shoe was to allow water to drain from the shoes. Today, brogues feature low heels, top caps, heel caps lace panels (like the Derby) and the presence of Broguing (or decorative) perforations.
Ted Baker Hann Dress Shoe
Made from imported leather and a synthetic heel, these dress shoes feature heels that measure about 1-inch. And in true brogue fashion, they feature a perforated trim and medallion toes with a lace-up vamp, allowing you to wear them with just about anything.
Cole Haan Lunargrand Wingtips
Who said a dress shoe can’t be comfortable? Outfitted with Nike’s Lunarlon outsole, these wingtips beg to differ. The imported oxford style shoes feature lace-up closures, blind eyelets and decorative brogueing at the seams. They’re sure to bring out the best in any outfit.
Church’s Downtown Suede Wingtips
Look to brands like Church’s for shoes that bring a contemporary flair to traditional styles. For example these ‘Downtowns’ are crafted from navy suede in the sleek oxford shape, set to red brick soles for a noticeable yet classy contrast.
There are many stories alluding to the origin of the loafer. However,the widely accepted theory is that of a Norwegian man who “borrowed” the style from Native American footwear (moccasins) thus creating a hybrid between that and Norwegian footwear. From here, there exists a multitude of off-shooting styles to choose from, depending on personal preferences.
Broken down, you can expect to find several common characteristics across the loafer style. For starters, these are laceless shoes in which the ankle is exposed. Many also feature a separate sole and an often low heel. The upper vamp boasts a moccasin-like construction and sometimes you’ll notice a saddle (a piece of leather across the vamp) on the shoes as well.
Alden Tassel Loafers
The Alden Shoe Company was founded in Mass. in 1884. Since then, quality has only improved for the oldest shoemaker in New England. And these U.S.-made elegant tassel loafers are a testament to this quality with a leather upper, lining, and sole providing both durability and comfort to loungers everywhere.
O’Keeffe Samuel Suede Penny Loafers
For those looking towards foundational wardrobe footwear, O’Keeffe certainly delivers. Handcrafted with the softest suede by Italian artisans, these penny loafers are set to last through frequent wear, perfect as a staple for any style. Rock them as evening wear or an impromptu Saturday at the office.
Abe Penny Loafer
Those who still value the virtues of humility in the absence of shimmer and shine will find solace in these comfortable yet classy penny loafers. Featuring a full-grain calfskin upper and handcrafted in Spain, these silent loafers are sure to provide comfort and reliability, because after all, isn’t that what it’s all about?
What sets the monk strap apart from other shoes discussed thus far is their versatility. Because of their simple yet sleek design they can be worn in multiple environments and in various settings. They fit any occasion from an important business meeting to a night out with your lady.
The monk strap origins date back many centuries to Europe, commonly worn by, yup you guessed it, monks, who were looking for shoes that offered more protection than the sandals they normally wore. They were also well-suited as a durable work shoe. In the centuries since, the monk strap evolved quite well to the versatile, classy men’s shoe it is today.
FRYE James Double Monkstrap
Keeping in line with tradition, the James Double Monkstrap offers a no-frills design in an imported all leather composition. Wear this shoe to either dress down a professional wardrobe or dress up a casual night out. The old school shape and feel of these shoes will no doubt add some swagger to your step.
Few things in this world strike affluence more that Italian leather. And it’s clear Billy Reid had this notion in mind when crafting these cognac calfskin monk strap shoes in Italy. Each shoe is finished with a cap toe and stitched to a leather sole and stacked heel. You’ll notice these shoes carry with them a serious “wow” factor.
Cole Haan Cambridge Monk Oxford
The single strap monk is a classic European style. This particular design features a simple gold buckle with subtle brogue details on the soft leather upper. You’ll also find an elegant full leather outsole and lined leather and fabric comprised on this piece as well.
Though you wouldn’t know it at first glance, Chelsea boots are rooted in the Victorian era when J. Sparkes-Hall used vulcanized rubber to make boots for Queen Victoria. This made the boot easy to slip on and off due to the elastic and durable rubber material.
Today, the Chelsea is characterized by several defining features. Most have rounded toes and are at ankle length. Both the vamp and the quarters are made from a single piece of leather, giving the boot its smooth streamlined appearance. Also, the elastic strip tends to extend just below the ankle though not all the way to the sole. Again this allows for easy access and removal of the boot.
Now, though these Chelsea’s don’t feature leather, they still remain true to the style of the original. Made in Italy, these suede boots easily pull on and feature a rubber crepe sole, tapered toe, and elasticized ankle gores and pull tab for assistance. Don’t let the name fool you, these are anything but common.
Grenson is one of Britain’s most distinguished boot-makers, providing the Royal Kingdom with footwear since the 19th century. It’s these roots that make the Jacob Chelsea’s so authentic. And with premium upper leather, goodyear welt construction, and punched brogue detailing, you can’t go wrong here.
Snuff Rapello Suede
Let’s bring it back to the 21st century with these snuff suede and full rubber sole Chelsea boots. Each boot is goodyear welted, made to last, and get increasingly more comfortable over time. Its practical appearance will keep you warm in style. Wear them while bar-hopping on a mid-winter’s evening or a morning stroll.
Simply put, take the height of the Chelsea boot (about ankle length) add an outer lacing system and a leather or rubber sole and you have a classic men’s dress boot.
Originally designed for both the white and blue collar working man, these boots evolved over the years to the realms of both causal evening wear and urban hipsters. Featuring all leather vamps and quarters as well, you can be sure these boots will set off any wardrobe from the ground up.
Timberland Wodehouse Wingtip Boot
Featuring allover broguing detail, these round wingtip toed leather beauties come in medium brown and pair well with just about any outfit. In addition to the lace-up features, the Wodehouses come with a side zip closure to add extra snug value as well.
To Boot New York Stallworth Cap Toe
Here’s a glowing addition to any gentleman’s collection. Boasting hearty coloring and distinctive shine, these vintage-inspired boots will leave you feeling ready to hop on your Honda CX500 Cafe Racer and peruse the town.
Black Double Sole Lakeshore Boot
For those who like to paint it black, these black leather boots have your name written all over them. Each pair boasts oiled double leather Watercock soles, a stacked leather heel with dovetail toplift, and full calfskin lining. They’re also made in the USA – did we mention they’re black?
With an odd name, the word Chukka comes from the game of Polo; derived from the seven and a half minute Polo playing period called a Chukker or Chukka. Another derivative of the term is thought to be the Indian use of the word ‘chukkar,’ in the context of taking a leisurely stroll or walk.
In fact, the first Chukka boot was worn in the US in 1924 by the Duke of Windsor, who had visited India before his arrival in the states. Regardless, they soon took off in popularity, and by the 1940s and 50s Chukka boots were considered a comfortable alternative that could be worn as both casual and dress boots.
Classic Macalister Boots in Suede
This classic style is inspired by the crepe-soled boot worn by World War II British officers. They’re made from fine Italian suede and only get better as they age. J.Crew also left them unlined for a more casual feel.
Seavees Eye Chukka Boot
Made from 100 percent cow hide atop a crepe sole, these chukka boots will only get more comfortable as you wear them. It’s a classic ankle boot with a three-eyelet design, seamless toe, and contrast stitching for a smooth look and feel.
Featuring two eyelets and sleek leather, the Brady is the perfect complementary shoe to your best jeans. The footbed is also lightly cushioned for additional comfort and it’s lace-up closure allows for an adjustable fit for all foot shapes and sizes.
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