Looking sharp and stylish has never been easier with our guide to the best dress shoes for men. Whether you're dressing up for a fancy night out or just want to elevate your everyday style, we've got you covered. From classic oxfords to trendy sneakers, we've handpicked the top brands and styles that will have you stepping out with confidence. So get ready to put your best foot forward and explore our curated selection of the finest dress shoes for men.


If you only have one pair of dress shoes in your wardrobe, consider getting an Oxford. It's a versatile style that can work for formal occasions, such as big work events or black tie affairs. The "closed-throat" construction of an Oxford, where the leather around the laces meets at the base and is sewn into the vamp, gives it a sleek silhouette. You can easily identify an Oxford by looking at the top of the shoe near the eyelets – if it forms a "V" shape instead of parallel lines, it's an Oxford.

The Oxford


The Oxford shoe is a classic dress shoe that is known for its elegance and sophistication. It typically comes in black and features closed lacing construction. The most common style is the cap toe, which has a capped toe and can be worn for various dressy occasions. Another type of Oxford is the wholecut, which is made from a single piece of leather and often showcases unique patina techniques.

Traditional monk straps

Marco II Monk Strap ShoeVersatility is the key factor when it comes to formal shoes. Jim O’Brien, co-founder of Cleobella, recommends the single monk strap style for its ability to be dressed up or down for various occasions. He also praises its comfort, making it an excellent choice even for long hours of wear.

Cole Haan

Cole Haan is known for its high-quality men's dress shoes, which are highly regarded by style experts. GQ highlights the brand's Split-Toe Oxford, noting the comfort provided by Cole Haan's proprietary Grand soles. The shoes are praised for their durability and versatility.

Dress Boots

Dress boots offer a slightly rugged alternative to dress shoes while maintaining a refined style. They come in various styles, including lace-up options and ankle boots. Dress boots are ideal for fall and winter, as they provide added traction and durability in inclement weather.

  • An EVA midsole and cushioned footbed add comfort to a sturdy rubber outsole designed for all-season wear.
  • These classic boots are crafted from finely crafted leather and feature a shock-absorbing insole.
  • Made with high-quality materials, these boots offer both ruggedness and style.
  • Dress up these luxurious leather boots with a wool suit or pair them with chinos and a chambray shirt for a more casual look.

The Best Plain-Toe Dress Shoes

If you're looking for a dependable pair of dress shoes that will last, you'll need to invest a bit more. These shoes are designed to be durable and versatile, suitable for various occasions. Alden's plain toe blucher is a legendary silhouette made from high-quality Horween shell cordovan. It's a classic style that can be worn with both casual and more formal outfits. Magnanni's handmade plain-toe derbies are a more affordable alternative that still offers excellent quality and style. Beckett Simonon's whole-cut dress shoes, made from a single piece of leather, are another great option known for their craftsmanship and affordability.

The Best Wingtip Dress Shoes

Wingtip dress shoes, named for their wing-shaped broguing, are a luxurious and sophisticated choice. Church's Chetwynd wingtips, made in the UK with premium leather, exemplify the brand's commitment to craftsmanship and urban style. You can also find excellent wingtips available online, even from unexpected sources. These options provide great value for their quality and style.

Edward Green

Edward Green Piccadilly Leather Penny Loafers

Edward Green Chelsea Cap-Toe Burnished-Leather Oxford Shoes

Edward Green is a renowned Northampton-based shoe maker that produces exceptional dress shoes. Each pair is handmade with precision using the finest calf leather. The brand's commitment to high-quality craftsmanship is evident in every detail. With a range of luxury classics, including Chelsea Oxfords and Piccadilly loafers, Edward Green is a top choice for those seeking refined and stylish footwear.

The Best Monk Strap Dress Shoes

Monk strap dress shoes are a bold and fashionable choice. Known for their distinctive buckles, they add a touch of sophistication to any outfit. John Lobb's double monks, crafted in the UK with silver buckles and a Goodyear-welted rubber sole, make a powerful statement. They are perfect for pairing with a chalky peak lapel suit or cream-colored slacks and a dress shirt. Suitsupply and Ralph Lauren also offer exceptional monk strap options, representing a global take on this classic style.

The Best Dress Shoes for a Night Out

Toga Virilis' brogues offer a unique twist on the classic dress shoe. These shoes combine style with a touch of rebellion, featuring kiltie detailing and silver-tone hardware. They are perfect for adding a bit of edginess to your dress shoe collection and elevating your overall look. When choosing dress shoes for a night out, look for subtle yet stylish accents that make a statement and stand up to wear and tear.


Loafers have gone through a transformation and are no longer considered too casual for a suit. Penny loafers and bit loafers are the most popular styles. Penny loafers feature a strap with a cutout that can hold a penny (though the origin of this practice is debated). Bit loafers feature a metal piece across the foot for added style. Loafers are now sleek and stylish, making them suitable for even the sharpest formal attire.

The Loafer


Loafers, often considered casual shoes, deserve a place on this list of dress shoes. The modern-day loafer is believed to have originated from the moccasins worn by Norwegian fishermen. G.H. Bass commercialized the shoe in the 1930s, introducing the "Weejun" style. Today, loafers come in various designs, including penny, tassel, horsebit, and Belgian loafers. They are best suited for relaxed tailored outfits and can be an excellent choice for the summer season.

The Derby/Blucher


Derby shoes, also known as bluchers, are often confused with Oxfords. The main difference lies in the lacing style. While Oxfords have closed lacing, Derbies feature open lacing, with the eyelets sewn directly onto the upper. This gives the Derby shoe a less formal look compared to the sleek proportions of an Oxford. However, Derbies can still be worn with suits, especially when paired with unstructured blazers and tailored trousers. The suede buck is a variation of the Derby, with the shoe constructed in nubuck.

The Brogue


The term "brogue" refers to the decorative punched leather pattern applied to shoes and can be found on both Oxfords and Derbies. There are various types of brogue styles to be aware of. The wingtip brogue features an "M"-shaped pattern of brogueing on the upper and is commonly applied to Oxfords. The semi-brogue is a less decorative style with brogueing along the seam of the toe cap. The longwing brogue extends the perforated detail all the way back to the heel. Generally, the more brogueing a shoe has, the less formal it is. Rugged outdoor boots often feature elaborate brogueing, while smarter Oxfords have minimal brogueing limited to the toe cap.

The Best Men’s Dress Shoe Brands

Crockett & Jones

Crockett & Jones Sydney Suede Loafers

Crockett & Jones Lace-Up Leather Derby Shoes

Another well-established shoe maker in Northampton, Crockett & Jones has been a leader in the British luxury shoe industry since 1879. Each pair of their shoes goes through a meticulous handmade process that includes over 200 separate operations and can take up to eight weeks to complete.

Crockett & Jones offers a wide range of classic dress shoes and dress boots that provide great value compared to other luxury brands. Their suede summer loafers are always stylish, and their Oxford shoes are an excellent choice for business attire, as they hold a Royal Warrant.

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The Best Brogue Dress Shoes

The brogue style of dress shoes is named after the distinctive perforations, or "broguing," found on the toe and edges of the shoe. Trickers is a brand that stands out with its exceptional brogue shoes. They specialize in refined dress shoes that are durable and stylish, often featuring robust Dainite soles that can withstand years of wear. Their Bourton derby shoe in rich black is specifically designed to elevate your navy suit from a corporate uniform to a stylish statement. These shoes can be paired with a tailored outfit or a casual combination of a gun check blazer, cashmere turtleneck, and dark indigo denim.

Many brands offer quality brogue shoes at affordable prices. Thom Browne's longwing brogues are a popular choice, while Thistle Shoes creates brogues inspired by traditional Scottish footwear, incorporating steel quarter tips and all-terrain rubber soles for durability and versatility.

Baudoin & Lange

Baudoin & Lange Sagan Classic Plain

Baudoin & Lange Sagan Classic Tassels

Baudoin & Lange played a major role in revitalizing the Belgian loafer style with the launch of their iconic Sagan loafer in 2015. Handmade in East London, their shoes have a luxurious and supple feel, resembling slippers more than traditional loafers. They are the perfect choice for relaxed yet elegant summer footwear, pairing well with linen or cotton tailoring.

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Berluti 1895 Venezia Leather Oxford Shoes

Berluti Lorenzo Scritto-leather Penny Loafers

Berluti was founded in 1895 by Italian shoemaker Alessandro Berluti and has grown into a globally recognized luxury fashion brand. While their footwear business remains a core focus, Berluti also offers a range of other fashion items. They are renowned for their handpainted patinas, which give each shoe a unique appearance. For those looking for truly distinctive dress shoes, Berluti is the ideal brand to explore.


Joseph Cheaney & Sons

Cheaney Andrew Derby Semi Brogue in Light Chestnut Calf Leather

Cheaney Hythe II R Wingcap Oxford Brogue in Mahogany Grain Leather

Cheaney & Sons, based in Northampton, was once owned by Prada but has now been restored to its former glory by two dedicated brothers. The brand specializes in handmade brogues and semi-brogues, all crafted in the same factory since 1900. Their shoes are known for their exceptional quality and attention to detail.

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Santoni Double Strap Leather Monk Shoes

Santoni Deponent Lace-Up Oxford Shoes

Santoni, founded by Andrea Santoni in 1975, initially gained fame as a secret treasure of Italy. Today, their handcrafted shoes are highly regarded for their exceptional quality and attention to detail. While renowned for their classic dress shoe styles, Santoni also offers a range of double monk strap shoes that display the brand's relaxed Italian style. Their shoes feature beautiful patinas on polished leather as well as woven leather and suede options, perfect for pairing with summer outfits.

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Salvatore Ferragamo

Salvatore Ferragamo Giovanni Leather Oxford Shoes

Salvatore Ferragamo Brown Gustav Loafers

Salvatore Ferragamo, a pioneer in shoe manufacturing, gained popularity in the 1920s with his comfortable and custom-made shoe designs for Hollywood stars. The brand is still headquartered in Florence, Italy, and remains a family-run business. While Ferragamo is well-known for its women's collection, their men's collection offers a range of exceptional dress shoes. From classic Oxfords to fashion-forward monk straps and loafers, Salvatore Ferragamo provides stylish options for every occasion.

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Allen Edmonds

Allen Edmonds stands out as a brand due to its innovative shoemaking techniques. Founded in America in 1922, Allen Edmonds revolutionized dress shoes by eliminating nails and the metal bar commonly found in other shoes, resulting in improved comfort. This technique is still used in their shoes today.

Allen Edmonds Men’s Park Avenue Oxford (allenedmonds.com) Forbes refers to Allen Edmonds Park Avenue Cap-toe Oxford Dress Shoe as the "Most Comfortable Overall," frequently recommended by stylists and podiatrists for its sleek silhouette and supportive fit. Unlike other comfortable dress shoes that may have orthopedic aesthetics, this lace-up oxford offers cushioning and forgiveness while maintaining a minimalist design. It features a low-profile silhouette, leather-lined interior, cork insoles that mold to your foot, and is available in ten different widths.

Trendsicle features Allen Edmonds' McAllister Black Wingtip Oxford Dress Shoe, which is a perfect choice to wear with a suit or pair with dark jeans for a stylish look.


When we talk about brogues, we're referring to the decorative detailing found on certain types of shoes. Originally, these perforations served a functional purpose, allowing water to drain out of shoes worn in Irish bogs. Now, they are primarily ornamental but remain a key feature of modern dress shoes.

Brogues are often referred to as wingtips, a term that stems from the decorative "wings" that extend from the toe of the shoe. Longwing brogues have wings that wrap around to the back of the shoe, while shortwing brogues wrap around to the mid-foot. However, brogue detailing can also be found on other types of shoes, such as cap-toes, derbies, oxfords, monkstraps, and even ankle boots. Ultimately, the choice of brogues comes down to personal preference.

Footwear, Shoe, Tan, Brown, Dress shoe, Oxford shoe, Caramel color, Cordwainer, Leather,

Monk Straps

Monk straps are a stylish choice that falls between traditional lace-up dress shoes and elegant loafers. These shoes feature one or two buckled straps on the upper, along with an additional layer of material held in place by the straps. They are particularly popular in warm weather and pair well with linen suits or lightweight dress pants.

  • The eye-catching bordeaux leather gives these shoes a premium look and feel, and the brogue detailing on the toe adds to their appeal.
  • Made in Portugal, these shoes are designed with a streamlined construction, while the polished leather adds a dressy touch.
  • The attention to detail sets these shoes apart, from the smooth single-monk strap design to the brogue cap toe perforations.
  • This pair is a splurge-worthy investment, meticulously built with over 200 steps.

What is the most comfortable type of dress shoes for men?

When it comes to choosing comfortable dress shoes for men, it's important to focus on specific features. Brad Schaeffer, DPM, a foot and ankle surgeon and expert podiatrist at New York City's Central Park SOLE, recommends looking for soft leather shoes with a wide toe box and removable insoles.

According to Schaeffer, the insole is the most crucial component for comfort as it provides support and stability with each step. A wider toe box helps relieve foot pressure and ensures a comfortable fit. Additionally, using insoles such as Dr. Scholl's can enhance comfort, provided that the dress shoes have removable insoles.

Schaeffer emphasizes that arch support and comfort are essential for both flat feet and high arches. Adding some cushioning to dress shoes can alleviate the rigidity often associated with them.

What makes a dress shoe formal?

A dress shoe is inherently more formal than casual sneakers, but there are key elements that define its formality. Opting for premium leather with a shiny, polished finish creates a more formal appearance compared to shoes made from burnished or hand-finished leather, which often have more texture and character.

For weddings or business formal settings, dress shoes made from flawless full-grain leather without visible scuffs or marks are ideal. However, in more business casual environments, you can be more flexible with your choice of dress shoes.

For instance, a pair of brown leather dress shoes or boots with brogue detailing or casual burnishing can be paired with tan chinos, a light blue Oxford shirt, and a lightweight navy blazer for a classic business casual look. The same combination can also be effortlessly styled with blue jeans in most settings.

Ultimately, having a couple of high-quality, versatile dress shoes in your rotation is a worthwhile investment for any man.

The Best Cap-Toe Dress Shoes

Looking for a versatile pair of dress shoes that can be worn to various formal occasions? Look no further than a black cap-toe shoe. These all-around winners ensure you'll never violate any obscure dress codes and can wear them with confidence. When it comes to quality and style, George Cleverly's shoes are in a league of their own. Hand-cut in England and featuring subtle detailing along the seams, they withstand the ever-changing trends of fashion. You can even wear them for a wedding or, if you so choose, be buried in them. Just make sure you get your hands on a pair.

While a leather lace-up will never provide the same comfort as a running shoe, the signature insoles from Allen Edmonds come pretty close. If you don't want to splurge on a dress shoe, Johnston & Murphy offers a classic cap toe at an affordable price.


When it comes to men's dress shoes, Clarks may not be the first brand that comes to mind. However, they offer a wide range of comfortable and reasonably priced special occasion footwear. Luxe Digital describes their shoes as combining style, support, and budget-friendly prices, with dress shoes that look more expensive than they are.

Clarks Tilden Cap Oxford Dress ShoeClarks Tilden Cap Oxford Dress Shoe has received "Best Budget" accolades from People. The shoes pair well with a variety of dress pants, including chinos and blue jeans, making them suitable for both city commuters and formal events. These dress shoes offer exceptional quality for their price, with tight stitching, versatile colors, and comfortable construction.

Esquire recommends Clarks Whiddon Pace Oxford Shoe as a sporty option that not only features a bicycle-toe design but also a removable Ortholite footbed that wicks away moisture and absorbs impact.

While some reviewers noted that certain styles run slightly small, sizing up should ensure a good fit.

Leather chukka boots

Austin Chukka Boots$265 at Saks Fifth Avenue

Dress boots with the same body as derby shoes but a higher rise at the ankle offer a versatile silhouette. They can be both dressy and suitable for more informal settings. Myers recommends this style and often receives compliments when wearing them. He describes them as a "hack" to effortlessly look remarkable, even with a casual outfit. These boots feature sleek leather uppers for a polished look and cushioned insoles for added comfort.

Versatile boots

Captain BootsO'Brien highly recommends these versatile boots, which he calls his "daily go-to" for various occasions. The boots are suitable for more formal events and can be paired with casual daytime outfits. Offering durability and comfort, they feature rubber outsoles, steel shank construction, and treated leather that develops a better look with age. With 13 different colors and finishes available, these boots can easily adapt to different outfit choices.

Sleek sneakers

Soft 7 City SneakerElevate your casual sneaker game by choosing a leather pair without excessive accents or logos. Such sneakers can be worn with dress clothes, offering both style and comfort. Personal stylist Rayne Parvis suggests wearing them as an alternative to brown lace-up dress shoes. Clients have praised this particular pair for its comfort, and it can be further customized with orthotics by removing the insert cushioning.


Derbies are a great casual option when it comes to men's dress shoes. They pair well with jeans, corduroy pants, and other slightly more relaxed trousers. The main distinction between derbies and Oxfords lies in their construction and lacing system. Derbies have open lacing, with shoelace eyelets sewn onto the top of the upper or vamp, which gives them a wider appearance.

  • These derby-oxford hybrids offer a straightforward design and come in wide sizes at an unbeatable price.
  • The athletic outsole and heat-activated insole provide both style and performance technology.
  • Burnished leather gives these shoes a unique look, and the tan color pairs well with blue denim.
  • Ethically handcrafted by artisans in Guatemala, these shoes feature a stacked leather heel and are fully resoleable.

Chelsea Boots

From Queen Victoria to Mods to Daniel Craig, Chelsea boots have been favored by influential British trendsetters. Although they are associated with affluent neighborhoods in London, this style has become globally popular and democratic. These ankle-height boots, usually made of leather or suede, can be worn throughout the year and for various occasions. A fitted suit with tapered trousers is the perfect match for Chelsea boots, reminiscent of the iconic Beatles' style in the '60s.


Chukkas are a versatile option but can range from more casual to refined depending on the style. The key is to choose chukkas with a streamlined silhouette and elevated construction. Typically shorter than average boots, they have a narrower toe and clean lines that sit nicely under suit trousers. Look for a not-too-chunky sole to maintain a sophisticated look.


Magnanni is renowned for its stylish footwear and exceptional craftsmanship. According to Brides, Magnanni's collection offers a wide selection of stylish men's dress shoes with quality materials and attention to detail. Whether you're looking for classic lace-up shoes or something more sophisticated like buttery leather loafers, Magnanni has options that exude flair.

Magnanni Men's Carver dress shoesMagnanni Men's Carver dress shoes have caught the attention of Men's Health, which highlights their textured leather upper, adding a mile of dressy style. The Spanish shoemaker's craftsmanship and hand-painted patinas justify the price point.

Travel Leisure recommends Magnanni's Corey Oxford Shoe, noting its extreme comfort and refined look. Although they may not be as plush as loafers or sneakers, these shoes are fantastic for various formal events. They offer a sophisticated and expensive appearance, making them worth the investment.

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Venetian Loafers

The Venetian loafer is a shoe that exudes elegance and luxury. It is not meant for casual wear, but rather for leisurely occasions or formal events. Some versions are even referred to as smoking or dinner slippers. These loafers are distinguished by their simple, unadorned upper made of leather or velvet. They are the epitome of pure and understated luxury.

Prop styling by Miako Katoh

Photography by Allie Holloway

Headshot of Jonathan EvansJonathan Evans

Jonathan Evans is the style director of Esquire, covering all things fashion, grooming, accessories, and sneakers. He resides in Brooklyn with his wife and son. You can follow him on Twitter and Instagram at @MrJonathanEvans.

Headshot of Barry SamahaBarry Samaha

Barry Samaha is the former style commerce editor at Esquire. He has a wealth of experience in the fashion and grooming industry, having worked for Harper's Bazaar, Surface, and WWD, as well as overseeing editorial content at Tod's Group. He has contributed to various publications such as The Daily Beast, Coveteur, Departures, Paper, Bustle Group, Forbes, and more. Based in New York City, he is a shoe enthusiast who is constantly looking for more closet space.

Avidan Grossman

Avidan Grossman is the Style eCommerce Editor at Esquire. He specializes in men's fashion, shoes, grooming, and accessories. With his impeccable sense of style, he devotes considerable time to deciding what to wear. Even so, his parents are still unsure of what he actually does.


Scarosso Classic Monk Shoes

Scarosso George Patent Leather Slippers

Scarosso may be a relatively young brand, established in 2010 by Moritz Offeney and Marco Reiter, both from Germany. While the administrative work is conducted in Berlin, Scarosso embodies the essence of Italian craftsmanship.

The shoes are produced in various family-run factories located in the Montegranaro region, renowned for its heritage in luxury shoemaking. Scarosso's direct-to-consumer model allows the brand to offer high-quality shoes at more affordable prices, delivering genuine Italian artisanal craft to a wider audience.

Based on personal experience (the writer of this article owns multiple pairs of Scarosso loafers), Scarosso consistently provides excellent value for a diverse collection of classic dress shoes.

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In the world of men's fashion, finding the perfect dress shoes can be a daunting task. But fear not, as we have compiled a comprehensive list of the best dress shoes for every occasion. From classic Oxfords and sophisticated monk straps to timeless wingtips and sleek loafers, we have left no stone unturned in our quest for elegance and style. Whether you're heading to a night out or a business meeting, our top picks such as Cole Haan, Edward Green, and Crockett & Jones are sure to make a statement. And for those looking to add a touch of flair, we recommend the exquisite brogue dress shoes from Baudoin & Lange or the sleek Venetian loafers from Scarosso. So go ahead, step into sophistication with these top-notch dress shoe options that will have you stepping out in style for any occasion.