When it comes to dressing for a formal occasion, one of the most essential elements for men is a good pair of dress shoes. But with so many options to choose from, how do you know which ones to go for? Should you opt for oxfords or loafers? And what about the different brands available? In this article, we will explore some key factors to consider when buying dress shoes and discuss popular styles and brands that are loved by men worldwide. So, if you're in need of some guidance on finding the perfect pair of formal shoes, keep reading to find all the answers you seek.


What To Consider About Dress Shoes


Following the emergence of a more casual dress code for men post-pandemic, men's dress shoes have also evolved. According to Turner, oxfords are no longer as popular as derbys and loafers, as simple designs have become more versatile and appealing.

Fit: Dombroski emphasizes the importance of considering foot shape rather than just shoe size. He advises focusing on fit, highlighting that foot length, width, and depth go beyond a specific size. It's also recommended to get professionally measured at a shoe store if you haven't done so in a while because feet tend to elongate and widen over time.

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

  • Remove the shoe's liner, stand on it, and visually check if it accommodates the length and width of your foot without causing rubbing on the sides, front, or heels, as suggested by Friedman.
  • Try on shoes with the socks you plan to wear with them, as advised by Friedman.
  • If a dress shoe feels uncomfortable initially, it's best to move on. According to Friedman, if it's squeezing your toes, it's unlikely to improve with time and may cause blisters and prolonged discomfort.

Shoe Shape and Width: Not all shoes offer wider widths, so if you have a wide foot or prefer more room at the bridge, look for styles that can accommodate your needs. Rounded toe styles are generally more comfortable than pointed ones because they allow your toes to move naturally and function better.

Sole and Insole: Leather and rubber are commonly used for soles, with rubber offering more flexibility and springiness. Vibram rubber soles, in particular, are preferred for their durability and comfort in urban environments. Lug soles are also popular due to their ability to withstand different terrains. According to Dombroski, rubber soles absorb shock better and provide more traction and comfort for high-stress areas, such as the balls of the feet.

Insole liners play a significant role in comfort. They act as a buffer and can have cushioning and arch support built into them. It's advised to check for removable liners, especially if you use orthotics.

Slip-On Versus Lace-Up: Lace-up dress shoes are considered the most versatile because they allow for adjustments to achieve the desired fit and reduce slippage, as pointed out by Friedman. Slip-ons, on the other hand, can be a stylish and comfortable option for those in creative or casual fields. However, individuals with a high instep and voluminous foot may find slip-ons uncomfortable due to the lack of adjustability.


What Brand Of Office Shoes Are Most Comfortable?


The choice of the most comfortable office shoes depends on individual needs and the office environment. According to stylists and podiatrists, Allen Edmond's dress shoes are a top choice for most men. They offer a sleek silhouette and supportive fit that works well across various dress codes. Peter Millar's sneakers strike a balance between formal and laidback with athletic features, making them a more casual option. Cole Haan is another reputable brand that prioritizes comfortable construction combined with stylish aesthetics.


Do Most Men's Dress Shoes Come In Different Widths?


Several popular brands, including Johnston & Murphy, Allen Edmonds, Rockport, Stacy Adams, and Cole Haan, offer dress shoes in different widths. Another option to achieve a wider fit, according to experts, is to remove a shoe's insole to allow the foot more room to spread out. Dombroski recommends this method if a shoe doesn't come in a wide width, as it can potentially provide extra space if needed.


How Can I Tell If A Dress Shoe Fits?


Dombroski outlines a few guidelines for determining if a dress shoe fits correctly:

1. There should be approximately a quarter of an inch of room between the end of your longest toe and the end of the shoe to accommodate movement and swelling throughout the day. This space may vary for running shoes.

2. The shoe width should not feel constricting, allowing for slight toe wiggling.

3. Remove the shoe's insole and stand on it on the ground. If your foot fits within the outline of the insole, it's a good indication of a proper fit. If the fourth and fifth toes don't fit, it's advisable to try another shoe.


Can Men's Dress Shoes Be Dressed Down?


Yes, men's dress shoes can be dressed down. Rounded, English-style toes, pebbled leather, and chunky soles are considered casual and versatile. Dress shoes such as derbys, brogues, slip-ons, or loafers can be worn with a variety of outfits, including denim, khakis, and dress pants.




If you're looking for a versatile dress shoe for formal occasions, consider oxfords. They have a "closed-throat" construction, with the leather around the laces meeting at the base and sewn into the vamp. This sleek silhouette ensures a polished look suitable for professional or formal events.

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Derbies are slightly less formal than oxfords but are still versatile. They pair well with various suits and can also be worn with jeans or tweed trousers. The open-throat silhouette, with the leather running parallel and over the vamp, adds a touch of modernity to any ensemble.

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Brogues refer to the decorative detailing on dress shoes, originally designed to drain water. They often feature perforations and come in various styles, including longwings and shortwings. The perforations can be found on cap-toes, derbys, oxfords, monkstraps, or even ankle boots. Brogues allow for personalization and add character to your footwear.

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Loafers were once considered too casual for formal wear but have since become acceptable with suits. Penny loafers and bit loafers are common styles. Penny loafers feature a strap with a cutout that was traditionally believed to hold a penny. Bit loafers have a metal piece across the foot for decorative purposes. Loafers are a stylish slip-on option suitable for both formal and casual occasions.

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Chukkas offer versatility and can be either casual or refined. The key is to choose a streamlined silhouette with a narrower toe and clean lines. Chukkas typically have a shorter boot height, making them suitable for pairing with suit trousers. Look for chukkas with a not-too-chunky sole for a sophisticated appearance.


Chelsea Boots


Chelsea boots have a rich history, from being popularized by British trendsetters to becoming a global shoe style. They are ankle-height boots made of leather or suede that can be worn throughout the year and for various occasions. Chelsea boots look particularly stylish when paired with a fitted suit featuring tapered trousers.


Monk Straps


With their unique design, monk straps provide a secure fit without laces. They feature one or more straps that fold over the vamp and fasten with buckles on the ends. Originating in the 15th century and worn mainly by monks, monk straps have evolved over time. Modern iterations come in different materials, colors, and designs, making them a popular choice for those seeking a reserved yet elevated shoe style.


Vegan minimalist


Shop the Itoki Vegan Oxford for at Matt & Nat

For those who prefer a cruelty-free and minimalist approach to fashion, the Itoki Vegan Oxford is the perfect choice. Made by Matt & Nat, a popular Montreal-based brand known for using eco-friendly materials, these dress shoes are crafted with biodegradable polyurethane. The clean lines and timeless design make them versatile and suitable for any occasion. Not only are they stylish, but they are also comfortable to wear, according to Nolan Beck-Rivera, an interior designer and owner of Jolene, a home goods shop based in Richmond, Va. He appreciates that these shoes are ethically made without causing harm to animals.


Leather chukka boots


Find the Austin Chukka Boots for $265 at Saks Fifth Avenue

Classic and sophisticated, the Austin Chukka Boots are a popular choice among boot enthusiasts like Myers. These boots feature a higher rise at the ankle, giving them a chukka-style silhouette. Myers receives regular compliments when wearing these boots and considers them a "hack" for looking effortlessly remarkable. The leather uppers provide a sleek appearance, while the cushioned insoles ensure comfort throughout the day.


Heeled style


Upgrade your footwear collection with the Wyatt 40 Leather Zip Ankle Boots for 3 at MyTheresa

Sharpton, known for his daring fashion choices in the beauty industry, loves to add personality to his outfits. He praises these Wyatt Western Zipped Boots for being amazing in both style and comfort. The almond toe, smooth black leather, and stacked heel give the boots a formal yet rockstar-inspired vibe. The interior zipper makes them easy to slip on and off, while the rubber Vibram soles provide added comfort. Sharpton prefers the white version of these boots, as it adds attitude to any look.


Versatile boots


Discover the Captain Boots in Terracotta for $199 at Thursday Boot Company

When it comes to versatility, the Captain Boots from Thursday Boot Company are unbeatable. O'Brien, who considers them his daily go-to pair, wears them for both dressy occasions and casual daytime outfits. These boots are not only stylish but also durable, thanks to their rubber outsoles, steel shank construction, and treated leather that develops a beautiful patina over time. With 13 different colors and finishes available, you can easily adapt these boots to suit your personal style and wardrobe needs.


Statement slip-ons


Make a statement with the Leather Chelsea boots for 3 at MyTheresa

For those seeking a bold and fashion-forward look, the Leather Chelsea boots are the perfect choice. These boots, available at MyTheresa, feature a sleek design and are praised by Beck-Rivera as being comfortable and stylish. The rubber Vibram soles provide excellent traction, while the white color adds attitude to any outfit.


Sleek sneakers


Upgrade your sneaker game with the Soft 7 City Sneaker in Cognac for $159.95 at Amazon

For those who want to elevate their casual looks, the Soft 7 City Sneaker by ECCO is a perfect choice. These leather sneakers offer a refined take on the classic sneaker style and are free of any busy accents or logos. Personal stylist Rayne Parvis recommends wearing these sneakers as a dress shoe alternative, especially in brown. Clients praise their versatility and comfort, with some even opting to replace the insert cushioning with their own orthotics for added support.


Luxe lace-ups


Indulge in luxury with the Original Achilles Sneaker for $425 at Saks Fifth Avenue

When it comes to sophisticated and luxurious lace-up sneakers, the Common Projects Original Achilles Sneaker is a top choice. According to Parvis, these sneakers are favored by both stylists and clients for their understated and dapper design. Instead of a logo, these sneakers feature a string of numbers on the side, which has become synonymous with the brand's exclusivity. Crafted with high-quality leather, these sneakers are a testament to fine craftsmanship and timeless style.


Cole Haan


Cole Haan’s men’s dress shoes have received high praise from style experts. According to GQ, the brand's Split-Toe Oxford, with its proprietary Grand soles, is renowned for its comfort and quality. Its unparalleled foot massagers have left customers reluctant to try any other brand.


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When it comes to sizing, DMARGE emphasizes that Cole Haan offers extended sizes and widths, eliminating the need to rely on age-old brands for high-quality men's dress shoes.

Plus, Cole Haan doesn't compromise on style for the sake of comfort. Trendsicle highlights the brand's ØriginalGrand Wingtip Oxfords, highlighting their grooved rubber soles that give them a trendy and youthful appearance. Despite their fun look, they still maintain a formal and sophisticated feel, making them ideal for long days on your feet.




Magnanni is renowned for its stylish and expertly crafted footwear. Brides notes that the brand offers a wide selection of stylish men's dress shoes, including lace-up shoes and buttery leather loafers. Each pair exudes quality craftsmanship and some even feature unique and eye-catching designs.

Magnanni's Vaughan Leather Oxfords have caught the attention of Men's Health, who praises their textured leather upper that adds a touch of style to any outfit. The Spanish shoemaker's meticulous hand-painted patinas have also not gone unnoticed, further justifying their price point.

Travel Leisure suggests the brand's Corey Oxford Shoe, highlighting its exceptional comfort. These shoes may not be as plush as a loafer or sneaker, but they still provide unrivaled comfort without sacrificing style. They exude an expensive and refined look, making them suitable for both formal and casual occasions.




Clarks may not be the first brand that comes to mind when thinking of men's dress shoes, but Luxe Digital highlights their extensive line of comfortable and affordable special occasion footwear. The brand manages to combine style, support, and budget-friendly prices, offering a range of perfectly designed dress shoes that look far more expensive than their price tags suggest.

Clarks' Tilden Cap Oxford Dress Shoe has been recognized by People as the best budget-friendly option. These shoes pair well with various dress pants, making them versatile for both work and formal events. Reviewers praise their exceptional quality, including tight stitching, versatile colors, and sturdy yet comfortable construction.

Esquire points out Clarks' Whiddon Pace Oxford Shoe, which combines a sporty design with a comfortable fit. Not only does it feature a bicycle-toe design, but it also has a removable Ortholite footbed that wicks away moisture and absorbs impact, ensuring maximum comfort throughout the day.


Allen Edmonds


What sets Allen Edmonds apart? According to DMARGE, the brand's commitment to comfort led them to employ new shoemaking techniques. They eliminated nails and the metal bar used under the instep, focusing on comfort and craftsmanship. This technique remains in use today.

Forbes hails Allen Edmonds' Park Avenue Cap-toe Oxford Dress Shoe as the most comfortable overall. These shoes are often recommended by stylists and podiatrists for their sleek silhouette and supportive fit. Despite their comfort-focused design, they maintain a minimalist and visually appealing look. They feature an updated low profile, leather-lined interior, cork insoles that mold to your foot, and are available in ten different widths.

Trendsicle spotlights Allen Edmonds' McAllister Black Wingtip Oxford Dress Shoe, describing it as the perfect dress shoe for pairing with suits or dark jeans. Its versatile style makes it suitable for various occasions, while its craftsmanship and attention to detail set it apart from other brands.


Beckett Simonon


Beckett Simonon prides itself on providing quality and affordable custom dress shoes. Brides points out that the brand offers a variety of different styles to choose from. Additionally, their made-to-order business model promotes smarter consumption, lean production with zero unsold inventory, and less waste, adding a layer of sustainability to their products.

GQ highlights Beckett Simonon's Valencia Wholecuts Shoe, emphasizing that they are crafted from a single piece of leather, a process that would typically cost five times more. These shoes showcase the brand's commitment to exceptional craftsmanship and quality.

Men's Health recognizes Beckett Simonon's Hoyt Monkstraps as the best monk strap shoes. These shoes offer a dressy option for work and are traditionally less formal than oxford shoes. Despite their less formal nature, they are still comfortable and stylish.


Edward Green


Edward Green is renowned for its exceptional dress shoes. Founded in 1890, the brand has been synonymous with handmade precision and the use of the finest calf leather hides. Each week, only around 250 pairs of shoes are completed, showcasing the brand's commitment to artisanship and attention to detail.

Forbes names Edward Green's Piccadilly Leather Penny Loafers as the most luxurious dress shoes. These loafers exude elegance and sophistication, making them a timeless addition to any wardrobe. Pairing them with a variety of outfits will elevate your style to new heights.

Edward Green's Chelsea Cap-Toe Burnished-Leather Oxford Shoes offer a unique and distinguished look. Their handpainted patinas set them apart, ensuring that each pair is truly one-of-a-kind. If you're in the market for a truly unique and high-quality dress shoe, Edward Green is the brand to explore.




Berluti, originally a leather shoe specialist, has evolved into a globally recognized luxury fashion brand. The company has never lost sight of its footwear business, continuing to produce top-tier wholecut Oxfords.

Mr. Porter showcases Berluti's 1895 Venezia Leather Oxford Shoes, highlighting their exquisite craftsmanship and attention to detail. These shoes exude elegance and sophistication, making them a statement piece for any occasion.

Berluti Lorenzo Scritto-leather Penny Loafers offer a unique and eye-catching design. With their handpainted patinas, these loafers are truly one-of-a-kind. If you're looking for a dress shoe that stands out and showcases your individuality, Berluti has the perfect options.


Joseph Cheaney & Sons


Joseph Cheaney & Sons, based in Northampton, is dedicated to preserving the artistry of shoemaking. Handmade in the same factory since 1900, Cheaney's brogues and semi-brogues are renowned for their exceptional quality and attention to detail.

Cheaney's Andrew Derby Semi Brogue is crafted from light chestnut calf leather, giving it a stylish and sophisticated appearance. These shoes are designed to elevate any outfit and exude timeless charm.

For those seeking a classic brogue, Cheaney's Hythe II R Wingcap Oxford Brogue offers a mahogany grain leather option. These brogues showcase the brand's commitment to traditional craftsmanship and are a testament to their legacy in handmade shoe production.

When it comes to quality, style, and craftsmanship, Joseph Cheaney & Sons is a brand you can trust.





Santoni Double Strap Leather Monk Shoes


Santoni Deponent Lace-Up Oxford Shoes

Santoni, founded in 1975 by Andrea Santoni, was Italy's well-kept secret until recently when it gained recognition from discerning shoe enthusiasts worldwide. The brand remains family-run and renowned for its exceptional craftsmanship and attention to detail. While Santoni offers a range of classic dress shoe styles, it is particularly acclaimed for its exquisite double monk strap shoes. This is not surprising since the Italian tailoring style exudes a more relaxed vibe compared to its British counterpart. In addition to the beautifully polished leather versions, Santoni also features intricately woven leather and suede variations that are perfect for pairing with summer ensembles.

Explore the collection at Farfetch


Salvatore Ferragamo



Salvatore Ferragamo Giovanni Leather Oxford Shoes


Salvatore Ferragamo Brown Gustav Loafers

Salvatore Ferragamo emerged as a pioneer in the shoe manufacturing industry, garnering fame among Hollywood starlets in the 1920s with his comfortable yet stylish footwear tailored to perfection. After achieving success, the shoemaker returned to Florence, Italy in 1927, where the brand's headquarters reside to this day. The Ferragamo family continues the legacy with their dedication to exquisite craftsmanship. While Ferragamo is widely recognized for its women's collection, its men's line is equally magnificent. The collection showcases a stunning array of Oxford and Derby styles, as well as more fashion-forward monk straps and loafers.

Discover the collection at SSENSE

When it comes to finding the perfect formal shoes for men, there are endless options to choose from. From classic Oxfords and Brogues to trendy sneakers and slip-ons, the possibilities are as vast as they are stylish. Not only do brands like Cole Haan, Clarks, and Allen Edmonds offer a wide variety of designs, but they also prioritize comfort, ensuring that you can look polished without sacrificing foot happiness. Whether you opt for the sleek sophistication of Monk Straps or the rugged durability of Chelsea Boots, there is a shoe out there that fits both your style and your needs. So why settle for anything less than footwear that makes a statement and stands the test of time? Step up your shoe game and step out in confidence.