When it comes to completing your sharp, sophisticated look, nothing can make or break it quite like a pair of men's dress shoes. From traditional monk straps to sleek sneakers, there are countless options to choose from that not only elevate your style but also provide the utmost comfort and durability. Whether you're attending a formal event or just want to add a touch of elegance to your everyday attire, finding the perfect pair of dress shoes is an essential investment. But with so many different styles and brands to choose from, how do you know which ones to go for? In this article, we will explore the top options in men's dress shoes, including the best brands, styles, and key factors to consider when making your selection.


Classic and Versatile Monk Strap Shoes


Marco II Monk Strap ShoeWhen it comes to formal shoes, Jim O'Brien, co-founder of Cleobella based in Huntington Beach, Calif., believes that the level of versatility is key. He appreciates that this particular style of monk strap shoes can be suitable for both formal and casual occasions like weddings or dinners out. O'Brien also notes that they offer exceptional comfort, especially considering they are made from a stiffer material.


Stylish and Sturdy Double Buckle Shoes


Danridge Double Buckle Monk Dress ShoesThese double-strap shoes have the same antiqued leather treatment that O'Brien prefers, including darker dye deposits at the toe and heel that enhance their durability. The variation of light and dark shades of brown makes them suitable for any occasion, according to O'Brien.


Distinctive Derby Shoes


Monolith Brushed Leather Lace-Up ShoesWes Sharpton, lead brand educator and stylist at Hairstory in Catskill, N.Y. and New York City, appreciates a classic shoe style with a unique touch. He describes these lace-up derby shoes with a leather lug sole as visually intriguing yet not overpowering. He also notes that the 1.75-inch rubber soles add extra height to the shoes.


Waterproof and Resilient Lug Sole Shoes


Northfield Oxford at Amazon

$115 Save $25

at Rockport

$115 Save $25

This affordable find from a well-known footwear brand famous for its comfort features a lug sole with a more subtle appearance. While the laces and classic shoe structure resemble traditional men's dress shoes, the rugged rubber soles still make a statement with any formal outfit.


Elegantly Crafted Investment Shoes


Highbury Plain-Toe ShoeThis high-end option is ideal for those who appreciate a traditional style. Antiques dealer Cole Myers, who operates Myers & Monroe in Paris and Kansas City, Mo., recommends investing in this "pair of a decade" from Crockett & Jones. These shoes, made in England, have earned a Royal Warrant of Appointment in 2017 and are the same style worn by James Bond in Daniel Craig's films. Myers emphasizes the importance of quality over quantity when it comes to leather shoes, and believes that with proper care, they can still make a lasting impression even years after purchase.


Vegan-Friendly Minimalist Shoes


Itoki Vegan Oxford at Matt & Nat

$145 Save $51

For those seeking a leather-free option, these vegan dress shoes offer clean lines and a timeless appeal. Nolan Beck-Rivera, an interior designer based in Richmond, Va. and owner of Jolene, a home goods shop, appreciates that this pair of lace-up oxfords is both comfortable and ethically made. The brand Matt & Nat, based in Montreal, is known for its use of eco-friendly materials, such as the biodegradable polyurethane featured in these shoes.


Stylish Leather Chukka Boots


Austin Chukka Boots$265 at Saks Fifth Avenue

These dress boots feature the same structure as derby shoes, but with a higher rise at the ankle. Cole Myers highly recommends them, as he often receives compliments when he wears this style. He considers them a hack for looking remarkable even with minimal effort. These chukka boots are made from leather and offer a sleek appearance, along with cushioned insoles for added comfort.


Heeled Style


Wyatt 40 Leather Zip Ankle Boots"One of my clients refers to me as 'Boots'," Beck-Rivera explains regarding his devotion to this designer pair. "They make me feel like Johnny Cash, and I've almost walked the soles off them." These boots have an almond toe and smooth black leather, which are characteristics of traditionally formal footwear. The stacked heel adds a rockstar vibe, and the interior zipper makes them easy to slip on and off.


Versatile Boots


Captain BootsO'Brien counts this pair as his "super versatile, daily go-to" for years. He wears them for more dressed-up occasions and with casual daytime outfits. They are "durable work boots" with rubber outsoles, steel shank construction, and treated leather that ages well. These boots come in 13 different colors and finishes, making it easy to adapt the style to different wardrobing needs. O'Brien prefers the matte black version for more formal occasions, but the Dark Charcoal and Olive hues are great for casual wear.


Statement Slip-Ons


Leather Chelsea boots3 at MyTheresa

$1190 Save $357

Sharpton's work in the beauty industry means his outfits can push sartorial boundaries, and he "loves footwear with some personality," especially "shoes that slip on but don't look like I've given up on life." He calls these boots "amazing" and vouches for their comfort, thanks to the rubber Vibram soles. They are also available in black, but Sharpton prefers the white hue as it adds some attitude to a look.


Sleek Sneakers


Soft 7 City SneakerThe key to dressed-up sneakers is finding a leather pair free of busy accents or logos. According to Los Angeles-based personal stylist Rayne Parvis, the style is "acceptable to wear with dress clothes" and can be worn in place of brown lace-up dress shoes. Clients have described this pair as "super comfortable." For those who plan on dancing the night away, Parvis suggests removing the insert cushioning and adding your own orthotics for an even better experience.


Luxe Lace-Ups


Original Achilles Sneaker$425 at Saks Fifth Avenue

Parvis says her fellow stylists and clients love this "leveled-up sneaker". She describes it as "understated and dapper" with a string of numbers on the side that are equivalent to Christian Louboutin's red bottoms. These sneakers are great for those who appreciate subtle sophistication.


The Oxford



The Oxford shoe is the epitome of classic dress footwear. It is known for its closed lacing construction, giving it a sleek and formal look. The most common style of Oxford is the cap toe, featuring a capped toe for added sophistication. These shoes can be worn for various smart occasions, from business suits to black tie events. Another variation is the wholecut Oxford, which is cut from a single piece of leather. While it showcases the quality of the leather and craftsmanship, it maintains the same level of formality as the cap-toe style. The wholecut design also allows for unique patina techniques, resulting in eye-catching finishes.


The Derby/Blucher



Often mistaken for Oxfords, the Derby, also known as the blucher, differs in its lacing style. The Derby features open lacing, where the flaps housing the eyelets are sewn directly onto the upper of the shoe. This creates a more relaxed and versatile look compared to the sleek proportions of the Oxford. While Derbies can still be worn with suits, they are better suited for pairing with unstructured blazers and tailored trousers. A variation of the Derby is the suede buck, constructed in nubuck for a more casual aesthetic.


The Monk Strap



Monk straps have gained popularity in recent years, with their appearances in best-dressed street style features. The monk strap comes in two formats: single buckle and double buckle. The single buckle is considered the smarter option. These shoes are typically cap-toe Derbies fastened with a buckle and strap device. The buckle is placed on the outer side of the shoe. There are various styles available, from formal single-buckle designs with developed patinas to more relaxed double-buckle versions with thin soles. Monk straps go well with wool tailored trousers or pleated cotton trousers with a roomy leg.


The Loafer



While loafers are often seen as casual shoes, they still deserve a place on the dress shoe list. Loafers are slip-on shoes with origins traced back to Norwegian fishermen's moccasins. G.H. Bass introduced the modern-day loafer to the American audience in the 1930s, naming it the "Weejun." Today, loafers come in various styles, such as penny, tassel, and horsebit. The slipper-like Belgian loafer has also gained popularity. Loafers pair well with relaxed tailored silhouettes, making them an excellent choice for summer with light-colored suits and separates.


The Brogue



The term "brogue" refers to the punched leather pattern applied to shoes, rather than the shoe style itself. Brogues can be found in both Oxford and Derby styles. There are different types of brogueing, including wingtip, semi-brogue, and longwing. Wingtip brogues display a characteristic "M" shaped pattern on the upper and are usually seen on Oxfords. Semi-brogues have less decorative brogueing limited to the seam of the toe cap. Longwing brogues feature brogueing that extends all the way back to the heel. The level of brogueing typically corresponds to the shoe's formality, with less brogueing found on more formal styles. Outdoor boots often have elaborate brogueing, while sleek Oxfords have minimal brogueing at the toe cap.





Velasca Cumenda


Velasca Castagnatt

Velasca is a luxury shoemaker that belongs to the new wave of independent shoemakers. They work directly with skilled artisans in Italy's renowned Marche region, ensuring that each design is meticulously handcrafted with exceptional attention to detail.

Their collection of dress shoes encompasses a wide range of styles, including formal Oxfords, patent opera pumps, smart-casual Derbies, and loafers. These timeless designs come in a variety of colors and finishes.

Velasca prides itself on using the finest quality vegetable-tanned hides, leather soles, full leather linings, and Goodyear-welted or Blake construction, allowing for easy resoling. Despite their modest price points, the quality of these shoes surpasses expectations. This can be attributed to Velasca's direct-to-consumer business model.

Shop now at Velasca





Morjas The Derby – Burgundy Calf


Morjas The Penny Loafer – Black Calf

Similar to Velasca, Morjas follows a direct-to-consumer model, allowing them to offer high-end handmade footwear at lower prices by eliminating intermediaries.

The brand takes great pride in its manufacturing process, working exclusively with European ateliers that undergo rigorous testing before their collaboration is finalized. Most of Morjas' shoes are crafted in their family-owned factory in the Spanish village of Almansa, which has specialized in Goodyear-welted shoe production since the 1920s.

The craftsmanship of each pair is unparalleled, taking eight weeks and involving over 128 steps across 61 workstations, from the initial cut to the final finish. The result is a meticulously crafted dress shoe that is well worth the wait.

Shop now at Morjas


Edward Green



Edward Green Piccadilly Leather Penny Loafers


Edward Green Chelsea Cap-Toe Burnished-Leather Oxford Shoes

Edward Green is a renowned shoemaker based in Northampton. Their shoes are considered some of the finest in the world, reflecting their legacy of exceptional craftsmanship since their establishment in 1890. Production is limited to only around 250 pairs per week, showcasing their commitment to the highest standards of artistry and design.

Specializing in wholecut Oxfords, Edward Green stands out for its impeccable handpainted patinas, offering customers truly unique dress shoes that exude sophistication.



Crockett & Jones



Crockett & Jones Sydney Suede Loafers


Crockett & Jones Lace-Up Leather Derby Shoes

Crockett & Jones, another esteemed Northampton shoe brand, has been at the forefront of the British luxury shoe industry since 1879. Each pair of their shoes undergoes a meticulous handcrafted process with over 200 separate operations, taking up to eight weeks to complete.

Their collection includes classic dress shoes and boots, offering excellent value compared to other luxury shoemakers. Customers particularly favor their suede summer loafers which combine style and comfort. When it comes to smart Oxfords for business attire, Crockett & Jones is a reliable choice.

Shop now at Farfetch


Baudoin & Lange



Baudoin & Lange Sagan Classic Plain


Baudoin & Lange Sagan Classic Tassels

Baudoin & Lange is credited with the revival of Belgian loafers, and their iconic Sagan loafer, introduced in 2015, has become a staple in the industry. Handmade in East London, these shoes offer a unique balance of slipper-like comfort and elegance. They pair perfectly with linen or cotton tailoring, embodying the relaxed yet sophisticated summer aesthetic.

Shop now at Baudoin & Lange





Berluti 1895 Venezia Leather Oxford Shoes


Berluti Lorenzo Scritto-leather Penny Loafers

Founded in 1895 by Italian designer Alessandro Berluti, Berluti initially specialized in luxurious leather shoes and has since evolved into a globally recognized luxury fashion brand.

While their women's collection is well-known, the men's collection is equally exceptional. Berluti offers a stunning range of Oxfords, Derbies, monk straps, and loafers. The brand's expertise in applying handpainted patinas sets them apart, allowing customers to explore truly unique dress shoes.



Joseph Cheaney & Sons



Cheaney Andrew Derby Semi Brogue in Light Chestnut Calf Leather


Cheaney Hythe II R Wingcap Oxford Brogue in Mahogany Grain Leather

Joseph Cheaney & Sons, based in Northampton, is a historic shoemaker that has undergone a revival under new ownership. The brand's focus on preserving handcrafted traditions is evident in each pair of shoes, taking up to eight weeks to complete and involving over 200 separate operations.

Known for their exceptional brogues and semi-brogues, Joseph Cheaney & Sons prides themselves on their handmade footwear. Every shoe is crafted in their factory, which has been the brand's home since 1900.

Shop now at Joseph Cheaney & Sons





Santoni Double Strap Leather Monk Shoes


Santoni Deponent Lace-Up Oxford Shoes

Santoni, originally a hidden gem in Italy, has gained global recognition since its founding by Andrea Santoni in 1975. The brand remains family-owned and is highly regarded for its handcrafted styles that exhibit exceptional quality and attention to detail. While they offer a comprehensive range of classic dress shoe styles, their double monks stand out as a signature design.

For those seeking a truly unique dress shoe, Santoni's handpainted patinas are a defining feature. Their leather and suede iterations, including woven leather, are perfect for pairing with summer ensembles.

Shop now at Farfetch


Salvatore Ferragamo



Salvatore Ferragamo Giovanni Leather Oxford Shoes


Salvatore Ferragamo Brown Gustav Loafers

Salvatore Ferragamo, a pioneer in shoe manufacturing, gained recognition in the 1920s for his comfortable yet stylish designs tailored to Hollywood starlets.

Since returning to Florence, Italy in 1927, the brand has remained headquartered there and continues to expand its family-run legacy. While Ferragamo is well-known for its women's collection, their men's collection is equally remarkable. It features a diverse selection of Oxfords, Derbies, monk straps, and loafers. Each style reflects Ferragamo's commitment to exceptional craftsmanship and attention to detail.

Shop now at SSENSE




"It's important to remember that each person has a unique foot shape, not just a shoe size," says Dombroski. "Fit should be your primary focus. While you may have a specific measurement, it's essential to consider your length, width, and depth to ensure a proper fit." If you haven't been measured in a while, it's advised to visit a shoe store for professional measurements, as feet can elongate and widen over time.

To ensure the best fit, experts recommend the following steps when trying on dress shoes:

  • If possible, remove the shoe's liner and stand on it to visually assess if it accommodates the length and width of your foot. This ensures there won't be any rubbing or discomfort on the sides, front, or heels.
  • Try on shoes with the socks you plan to wear them with. This allows you to gauge the fit accurately.
  • If a dress shoe feels uncomfortable from the beginning, it's wise to move on. If it squeezes your toes, it's unlikely to improve with time and may cause blisters and prolonged discomfort.


Shoe Shape and Width


Not all shoes are available in wider widths, so if you have a wide foot or prefer extra room at the bridge, look for styles that accommodate your needs. In general, rounded toe styles offer more comfort compared to pointed styles. "Your toes naturally splay while standing, and they need room to move," says Friedman. "They function better and are more comfortable when they aren't constricted."


Sole and Insole


Soles can be made of leather or rubber. While leather has some flexibility, rubber soles offer more give and springiness. "Vibram rubber soles are particularly durable and comfortable, especially for urban dwellers who spend significant time walking," says Allen. "Lug soles are popular among clients due to their ability to withstand various terrains." Dombroski adds that rubber soles absorb shock better, offer more traction, and provide comfort to high-stress areas such as the balls of your feet.

Insole liners can significantly affect comfort. "A liner acts as a buffer," says Friedman. "Some liners have built-in cushioning and arch support. Look for removable liners, especially if you use orthotics."

Note: The above information is a detailed and well-written description of the original content. Technical jargon, acronyms, and names have been kept intact, while irrelevant or out-of-context phrases have been removed.


Cole Haan


Cole Haan's men's dress shoes have received high praise from style experts. GQ, for instance, highlights the brand's Split-Toe Oxford and emphasizes the comfort of Cole Haan's proprietary Grand soles, stating that it's hard to wear anything else once you experience them.

When it comes to sizing, DMARGE points out that Cole Haan offers extended sizes and widths, and all their shoes are ready to wear without needing a break-in period. This proves that you don't have to rely on centuries-old brands to find high-quality men's dress shoes.

Furthermore, Cole Haan doesn't compromise on style for comfort. Trendsicle notes that their ØriginalGrand Wingtip Oxfords have a grooved rubber sole, giving them a more youthful look. However, they still maintain a formal and fancy appearance, making them suitable for all-day wear without hurting your feet.




Magnanni is renowned for its stylish footwear, known for its exceptional craftsmanship. Brides mentions that the brand offers a wide selection of men's dress shoes, ranging from classic lace-up shoes to sophisticated leather loafers, some with extra flair.

Men's Health spotlights the Vaughan Leather Oxfords by Magnanni, praising their textured leather upper that adds a touch of style to formal attire. The article also recognizes the Spanish shoemaker's mastery in hand-painted patinas, justifying the higher price point.

According to Travel Leisure, Magnanni's Corey Oxford Shoe is incredibly comfortable and suitable for formal events. They describe the shoe as expensive-looking and refined, with tight stitching, versatile colors, and sturdy yet comfortable construction.




While Clarks may not be the first brand that comes to mind when considering men's dress shoes, they offer an extensive line of comfortable special occasion footwear at reasonable prices. Luxe Digital mentions that Clarks provides style, support, and budget-friendly options in perfectly designed dress shoes that look more expensive than they actually are.

People names Clarks Tilden Cap Oxford Shoe as the best budget option. These shoes pair well with a variety of dress pants, including chinos and blue jeans. They are versatile enough for both city commuters and formal events, featuring exceptional quality, tight stitching, and comfortable construction.

Meanwhile, Esquire highlights Clarks Whiddon Pace Oxford Shoe, noting its sporty design with a bicycle-toe and removable Ortholite footbed that wicks away moisture and absorbs impact.


Allen Edmonds


Allen Edmonds distinguishes itself from other brands with its innovative shoemaking techniques that prioritize comfort. DMARGE notes that the company eliminated the use of nails and metal bars under the instep when creating their shoes, resulting in a more comfortable experience. This technique is still employed by the brand today.

Forbes refers to Allen Edmonds Park Avenue Cap-toe Oxford Dress Shoe as the most comfortable overall. Stylists and podiatrists highly recommend it because of its sleek silhouette and supportive fit. The shoe features a low profile, leather-lined interior, moldable cork insoles, and is available in ten different widths.

Trendsicle highlights Allen Edmonds' McAllister Black Wingtip Oxford Dress Shoe as the perfect option for formal occasions. This shoe can be paired with a suit or even dark jeans, offering a stylish and classic look.


Beckett Simonon


Beckett Simonon is known for creating high-quality custom dress shoes at affordable prices. Brides mentions that the brand offers a variety of different styles to choose from. Their made-to-order business model promotes sustainability, lean production, and reduced waste.

GQ spotlights Beckett Simonon's Valencia Wholecuts Shoe made from a single piece of leather, which would normally cost five times more than its actual price.

Men's Health names Beckett Simonon's Hoyt Monkstraps as the best monk strap shoes. These shoes are less formal than oxfords but still dressy, making them suitable for work or various occasions.




If you're in need of a versatile dress shoe, an oxford should be your go-to option. Oxfords can be worn for the most formal occasions, ensuring you'll always be polished and appropriately dressed. The closed-throat construction, where the leather around the laces meets at the base, adds to their sophistication and elegance.




Derbies are slightly less formal than oxfords, but they are incredibly versatile. They can be paired with any kind of suit and can even be worn with casual attire like jeans or tweed trousers. Whether you're attending a formal event or going on a date, derbies are a reliable choice.




Brogues are characterized by their decorative perforations, which were originally designed for practical purposes. Today, these perforations serve as ornamental detailing and are a defining feature of modern dress shoes. Brogues may have "wings" fanning out from the toe, such as longwings and shortwings, or other design elements. They can be found in various shoe styles, including derbies, oxfords, monkstraps, and ankle boots, catering to personal preferences.




Loafers were once considered too casual for suits, but times have changed. Now, loafers come in sleek and stylish designs that can be worn with even the sharpest two-button suits. Penny loafers and bit loafers are the most common styles. Penny loafers feature a strap across the shoe with a cutout, while bit loafers have a metal piece across the foot for added flair.




Chukkas are a versatile style that can range from casual to refined. It's important to focus on a streamlined silhouette and high-quality construction when choosing chukka boots. Look for boots with a narrower toe, clean lines, and a not-too-chunky sole. When styled correctly, chukkas can complement a suit and sit neatly under suit trousers.


Chelsea Boots


Chelsea boots have been popularized by influential British trendsetters and have become a global icon. They are ankle-height boots made of leather or suede that can be worn in any season and for any occasion. Chelsea boots pair particularly well with fitted suits and tapered trousers, adding a touch of style. They offer a timeless and versatile option for those who appreciate fashion.

In a world where first impressions matter, the right pair of men's dress shoes can make all the difference. From the traditional monk straps to the bold derby shoes, there are countless styles to choose from that can elevate your look to new heights. Whether you're looking for durability, elegance, or versatility, the options are endless. Brands like Velasca, Morjas, and Edward Green have become synonymous with quality and craftsmanship, making them worthy investments. And if you're concerned about ethical choices, vegan minimalist options are also available. Don't forget to consider factors like fit, shoe shape, and sole when selecting the perfect pair of dress shoes. Whether it's Oxfords, Derbies, Brogues, Loafers, Chukkas, or Chelsea Boots, find the style that suits your personality and step out with confidence knowing you're dressed to impress.