Written by Ben Chuang

Dress shoes are an essential aspect of your outfit if you choose to wear a suit. I know from personal experience that classic dress shoes can sometimes be uncomfortable, especially if I have to wear them all day.

That's why comfort is one of the key factors I consider when shopping for dress shoes or dress boots. I've done extensive research on various dress shoe styles to compile this list of the best dress shoes for both comfort and style.

 

Introduction to Men's Dress Shoes

Men's dress shoes are a cornerstone of a well-rounded wardrobe, embodying the intersection of style, sophistication, and functionality. Whether you're attending a formal event, navigating the corporate world, or simply aiming to elevate your everyday attire, the right pair of dress shoes can make a powerful statement.

Unlike casual footwear, dress shoes are designed to complement suits, dress pants, and other formal wear, ensuring that you not only look polished but also feel more confident. As with any investment in your wardrobe, choosing the right dress shoes requires an understanding of the various styles, materials, and design elements that set them apart.

While it may seem like a straightforward decision, the world of men's dress shoes is rich with options, each catering to different tastes and occasions. From the timeless elegance of Oxfords to the contemporary flair of monk straps, there’s a dress shoe style and matching collared shirt for every man.

In this article, we’ll explore the most popular styles, delve into the importance of material selection, and examine the design elements that can transform a simple shoe into a statement piece.

 

Classic Styles: Oxfords, Derbies, and Loafers

Oxford Shoes

When it comes to classic dress shoes, Oxfords, Derbies, and Loafers reign supreme. These styles have stood the test of time, each offering a unique blend of formality and versatility.

The Oxford shoe, characterized by its closed lacing system, is perhaps the most formal of the three.

This design creates a sleek, streamlined silhouette that pairs perfectly with a suit and professional dress shirt. Oxfords are often the go-to choice for black-tie weddings and other occasions where sophistication is key.

Derby Shoes

Derbies, while similar to Oxfords, feature an open lacing system, which provides a slightly more relaxed fit.

This subtle difference makes Derbies a bit more versatile, allowing them to be dressed up with a suit or dressed down with chinos or khakis for a business casual look. Loafers, on the other hand, are a slip-on style that combines comfort with elegance.

Their laceless design makes them an excellent choice for both formal and business casual settings, particularly in the warmer, summer months. Whether paired with dress pants or dark jeans, loafers offer a stylish yet understated option for men who value ease and versatility.

 

Modern Choices: Monk Straps and Brogues

While Oxfords, Derbies, and Loafers represent the pinnacle of classic men's footwear, modern styles like monk straps and brogues bring a fresh perspective to the world of dress shoes. Monk strap shoes are distinguished by their buckle closure, which replaces the traditional laces found on most dress shoes. This design element not only adds a touch of flair but also provides a secure fit.

Monk straps are available in single and double-buckle variations, with the latter offering a more striking visual appeal. These shoes are ideal for men who want to make a statement without sacrificing the formality of their outfits.

Brogues, on the other hand, are known for their decorative perforations, which add a layer of complexity and visual interest to the shoe. Originally designed as outdoor shoes in Scotland and Ireland, brogues have since evolved into a stylish option for formal wear.

The level of broguing can vary, with full brogues (or wingtips) offering the most intricate designs, and quarter brogues featuring more subtle details. Brogues can be worn with a wide range of outfits, from tailored suits to smart casual ensembles, making them a versatile addition to any wardrobe.

 

Best Men's Casual Dress Shoes

1. Allen Edmonds Newman Penny Loafer

The Allen Edmonds Newman Penny Loafers in Antique Bronze Leather is a top choice for the best men's casual dress shoes. Crafted from premium leather, this loafer combines classic style with modern comfort.

These penny loafers, with their sleek silhouette and subtle detailing, offer a versatile option that can effortlessly transition from the office to a casual night out, pairing easily with a short sleeve button up shirt. The cushioned insole and flexible rubber sole provide all-day comfort, making it perfect for men who value both style and ease.

Featured Review:

"I recently replaced my tried and true AE Cavanaugh loafers with a new pair. Upon comparison, the new loafers offer a more forgiving fit in the mid-foot area. The leather is a bit stiff at first, but after a week of wear, they are breaking in nicely. I expect them to last a long time, and I'm already receiving compliments on them. For sizing reference, I wear a size 9 in Nike, and for AE, I went with size 8D, which fits perfectly." - Christopher G.

2. Allen Edmonds Liverpool Chelsea Dress Boot

The Allen Edmonds Liverpool Chelsea Dress Boot in black leather is an elegant and versatile choice for those seeking a refined yet contemporary look. This boot features a sleek silhouette with a smooth leather upper, complemented by a flexible elastic side panel for easy wear.

The Goodyear welt construction ensures durability, while the cushioned insole offers comfort for all-day wear. The Liverpool Chelsea Boot combines classic style with modern functionality, perfect for smart casual occasions. These shoes also appear in our best chelsea boots for men guide.

Featured Review:

"The boots are quite superb in manufacture and a joy to look at. I wear a 10.5D in all Allen Edmonds but needed to purchase a pair in E as they are very slim fitting. A very versatile boot wearable with jeans, Chinos or a suit. A true staple for one’s closet." - Mark H.

3. Johnston & Murphy McGuffey Plain Toe

The Johnston & Murphy McGuffey Plain Toe in Tan Oiled Full Grain is an ideal choice for those seeking a stylish and comfortable casual shoe. Made from high-quality oiled full-grain leather, this shoe features a minimalist design with a focus on comfort. This shoe looks great when paired with a navy-patterned dress shirt.

The lightweight construction and cushioned footbed make it perfect for all-day wear, whether you're running errands or enjoying a casual day out. Its versatile look pairs well with jeans or chinos, especially if you're wanting to try a gray pants brown shoes outfit.

Featured Review:

"Just what I’ve been looking for. The quality is good. Comfort is good. Decent insole for my high arch. Fits well for my tricky wide feet. Speed of delivery good. It’s impossible to find wides in the brick-and-mortar stores anymore, so I’m thankful for this solution." - Roger W.

4. Allen Edmonds Trevor Plain-Toe Derby

The Allen Edmonds Trevor Plain-Toe Derby Dress Shoe in black leather is a versatile and sophisticated choice for the modern gentleman. Its sleek, plain-toe design offers a clean and minimalist look that pairs well with both formal and business-casual shirts.

Crafted with premium leather and a Goodyear welt construction, these comfortable dress shoes promise durability and long-lasting comfort. The cushioned insole adds to the comfort, making it an excellent option for all-day wear. As these shoes are also made in brown leather, you can definitely experiment with wearing a black suit with brown shoes.

Featured Review:

"This pair is for my daughter’s wedding, and as always, it’s a perfect fit with no break in period needed. This is my 20th pair of Allen Edmonds. Some are 40 years old and have been refurbished, and are still in service. Thank you for retaining your quality!" - Charlie S.

5. Johnston & Murphy Conard 2.0 Cap Toe

Elevate your footwear collection with the Conard 2.0 Cap Toe from Johnston & Murphy. This sophisticated black cap-toe shoe seamlessly blends classic design with modern comfort, featuring a sleek black full-grain leather upper and a refined cap toe for a polished appearance.

The Conard 2.0 is crafted with meticulous attention to detail, using premium materials and offering a cushioned footbed and flexible rubber sole for all-day comfort and durability. Perfect for the office or formal occasions, these high-quality shoes embody timeless elegance and professional style. And if you have too many pairs of black shoes like I do, get them in tan leather and try wearing a blue suit with brown shoes.

Featured Review:

"I've been wearing these almost a year. I've owned many shoes over the years that looked nice at first, but didn't last. I've gotta say that the Conard's have held up very well over the past year, and have retained their comfort. I wear them for work and they look sharp while being very comfortable. The only drawback is the laces that are starting to wear. Excellent shoe though." - Adam J.

Best Men's Black Dress Shoes

The Johnston & Murphy Melton Cap-Toe is a premium black dress shoe crafted from polished calfskin leather, ideal for formal occasions. It features a classic cap-toe design, Goodyear welt construction for durability, and a leather sole that provides a sleek finish.

The shoe is lined with soft leather for added comfort, making it a timeless choice that combines elegance with longevity. Perfect for everything from business meetings to black-tie events, the Melton Cap-Toe embodies the perfect blend of refinement and quality expected from Johnston & Murphy.

Featured Review:

"I really like the sleek design and how versatile they are, easily pairing with both formal and casual outfits. The quality of the materials and craftsmanship is evident, making the shoes not only stylish but also comfortable for extended wear. What I absolutely love is the attention to detail in the stitching and the overall durability of the shoes—they feel like they'll last for years. If there's one area for improvement, it would be the break-in period. The shoes were a bit stiff initially, but they became more comfortable after a few wears." - Carl N.

Material Matters: Leather, Suede, and Patent Leather

The material of a dress shoe plays a crucial role in its appearance, durability, and comfort. Leather is by far the most popular material, prized for its durability, breathability, and ability to develop a rich patina over time.

Full-grain leather, in particular, is the highest quality, offering a natural look and feel that improves with age. Shoes made from full-grain leather are an investment, often lasting for years with proper care. Calfskin leather is another popular choice, known for its soft texture and fine grain, making it a luxurious option for dress shoes. When wearing leather shoes, make sure to incorporate a matching belt.

Suede, while less formal than leather, offers a unique texture and a more relaxed aesthetic. Suede dress shoes are ideal for adding a touch of personality to your outfit, particularly in casual or smart-casual settings. However, they do require more maintenance than leather, as they are more susceptible to water and stains.

Patent leather, characterized by its glossy finish, is the material of choice for ultra-formal occasions. The shiny surface of patent leather shoes makes them a staple for black-tie events and formal ceremonies, where they are typically paired with tuxedos.

Choosing the Right Shoe for the Occasion

Selecting the right dress shoe for the occasion is essential for ensuring that your outfit is both appropriate and stylish. For formal events such as weddings, gala dinners, or important business meetings, a pair of classic Oxfords in black leather is the safest and most traditional choice.

Their sleek design and closed lacing make them the epitome of formal footwear. For slightly less formal occasions, such as office wear or semi-formal gatherings, Derbies or monk straps offer a bit more flexibility while still maintaining a polished look.

For more casual settings, such as weekend outings or business casual environments, loafers or brogues provide a stylish yet comfortable option. Loafers, in particular, are a versatile choice that can be easily dressed up or down, depending on the outfit.

When it comes to choosing the right color, black is always a safe bet for formal events, while brown or tan shoes offer more versatility for less formal occasions. The key is to match the shoe style and color to the formality of the event and the rest of your outfit, ensuring a cohesive and well-put-together look.

Care and Maintenance

Proper care and maintenance are essential to keep dress shoes looking their best and extending their lifespan. Regularly clean your shoes using a soft brush or cloth to remove dirt and dust, and apply a high-quality leather conditioner to keep the leather supple and prevent it from drying out.

Polish your shoes to maintain their shine and protect the leather, focusing on the cap toe and other high-wear areas. Store your shoes with cedar shoe trees to help them retain their shape and absorb moisture.

Avoid exposing them to excessive moisture or direct sunlight, and rotate your shoes to ensure even wear. By following these steps, you’ll preserve the elegance and functionality of your dress shoes.

 

Frequently Asked Questions about Men's Dress Shoes

What are the best men's dress shoes?

The best men's dress shoes combine style, comfort, and durability. When selecting dress shoes, you should consider classic options like Oxfords, Derbies, and Loafers. These styles are versatile and can be paired with a wide range of formal and semi-formal outfits.

Oxfords, in particular, are a timeless choice, known for their sleek design and closed lacing system, making them ideal for more formal occasions. Derbies, with their open lacing, offer a slightly more relaxed fit, perfect for business settings or less formal events. Loafers, on the other hand, are slip-on shoes that offer both comfort and style, making them a popular choice for everyday wear.

In terms of material, leather is the gold standard for dress shoes, offering both durability and a polished appearance. Full-grain leather, in particular, is highly regarded for its quality and longevity. However, suede can also be a stylish alternative, especially in more casual settings.

Which colour shoes is best for all dress for mens?

When it comes to versatility, black and brown are the go-to colors for men's dress shoes. Black dress shoes are the epitome of formality and can seamlessly pair with nearly any suit color, making them an essential part of a man's wardrobe.

Whether you're attending a formal event, a business meeting, or a wedding, black shoes are the safest and most traditional choice. They match particularly well with dark suits, including black, charcoal, and navy.

Brown shoes, on the other hand, offer more flexibility in less formal settings. They come in various shades, from light tan to dark chocolate, allowing you to choose the best match for your outfit. Brown shoes are perfect for pairing with navy, blue, or earth-toned suits.

They can also be worn with jeans or chinos for a smart-casual look. While black is generally more formal, brown shoes provide a versatile alternative that can be dressed up or down, making them a valuable addition to any wardrobe.

Who makes the best mens dress shoes?

Several brands are renowned for crafting the best men's dress shoes, each offering its own unique blend of quality, style, and craftsmanship.

Allen Edmonds is a standout brand, particularly known for its American-made shoes that combine traditional craftsmanship with modern designs. Their shoes are often Goodyear welted, meaning they can be resoled multiple times, making them a long-term investment.

Brands like Johnston & Murphy also offer a wide range of styles that cater to both classic and contemporary tastes.

For those seeking luxury, British brands like Church's and Crockett & Jones are synonymous with high-end, handcrafted shoes that are both stylish and durable.

These brands are often chosen by men who value timeless elegance and are willing to invest in footwear that will last for years.

What are the best quality mens dress shoes?

The best quality men's dress shoes are typically made from full-grain leather, which is the highest grade of leather available. This material is prized for its durability, ability to develop a rich patina over time, and resistance to wear and tear.

Shoes made from full-grain leather not only look better with age but also offer superior comfort as they conform to the shape of your foot.

Brands like Alden and Allen Edmonds are known for using high-quality materials and time-honored construction techniques, such as Goodyear welting, which adds to the durability and longevity of the shoes.

In addition to material and construction, attention to detail is a hallmark of high-quality dress shoes. This includes hand-stitched seams, leather linings, and carefully designed lasts that provide both comfort and a refined silhouette.