8 Best Casual Dress Shoes For Men – Easy Styling For 2024

First impressions always matter, so finding the perfect pair of casual dress shoes is a crucial endeavor for just about any man.

Let’s be honest, dress shoes are the gold standard when it comes to men’s footwear, but they’re often some of the least comfortable options in your closet. While sneakers might make it feel like you’re walking on a cloud, they feel out of place when attending nice events. So next time you’ve got an important meeting or a casual night out, why not throw on a shoe that will make a statement without sacrificing comfort?

Lucky for you, we’ve handpicked this list of the best casual dress shoes for men. Each of these options can serve a different purpose or fulfill a different lifestyle. Whether you’re looking to pick up something cheap or something expensive, this list should have you covered.

So, let’s step up your style with 8 of the best casual dress shoes for men.

Key Takeaways

To compile this list, I reflected on my experiences with each one of these brands and determined which shoe is best for which purpose. I also factored in style, material, and comfort because these are each important considerations for any shoe you buy. Overall, one of the best casual dress shoes for men is The Loafer from Amberjack. This is a modern take on the classic loafer, which is a staple of both casual and formal attire. Another great option is the Statesman from Thursday Boot Company with its slick and rugged design.

Why they’re great: The Loafer takes design cues from classic loafer styles and elevates them with modern technology. While these shoes may give off a formal appearance, they honestly feel more like sneakers when on your feet. This is due to the dual-function outsoles and heat-activated insoles which drastically increase comfort. Not to mention, these shoes feature many of the benefits associated with a typical pair of loafers, like the ability to be slipped on and off easily.

How to wear them: These loafers can be thrown on with most smart-casual outfits. They’d even look great with a pair of chino shorts and a short-sleeved button-up shirt during the warmer months.

Who are these for: The Loafer is for those who want a classic shoe design with a modern twist–something familiar, yet fresh.

Flaws but not dealbreakers: The profile of these shoes tends to run on the narrow side and they aren’t currently offered in wide sizes.

Sizes Available: 7-15 | Material: Full-Grain Leather/Suede | Colors Available: 11

Why they’re great: The Aurélien City Loafer is a unique take on the classic Loafer design. First off, this shoe has an ankle-high cut which essentially makes it a hybrid between a dress shoe and a boot. This loafer is also made with Aurélien’s supple “Softey” suede. Lastly, The smooth leather lining and refined rubber outsole ensure these shoes are comfortable for all-day walking.

How to wear them: These city loafers portray a distinctly European aesthetic. They can be thrown on with a classy polo and a pair of lightweight pants or shorts.

Who are these for: These are perfect for anyone desiring a unique and luxurious pair of shoes that also offer plenty of comfort.

Flaws but not dealbreakers: The City Loafers are only limited to 6 size options, so they might not be the best choice for men with larger or smaller feet than average.

Sizes Available: 40-45 | Material: French Calfskin Suede | Colors Available: 16

Why they’re great: The Velasca Baladüch shoe features a design reminiscent of a moc-toe boot, which is a timeless staple that will likely never go out of style. The chunky winter Vibram outsole is lightweight for its size, yet it offers a ton of traction in slippery environments. These shoes are also super easy to get on with an ankle-high cut that minimizes the need to untangle a web of laces.

How to wear them: These shoes are designed to be worn during the winter and in snowy climates. They might work as a fall shoe too, but they would likely be excessive for spring and summer.

Who are these for: These Baladüch shoes would be great for someone seeking reliable footwear to handle rain and snow. They’re also fairly chunky, so if you’re into that style, these could be perfect for you.

Flaws but not dealbreakers: These shoes may require some break-in time until they’re fully comfortable–especially with the smooth leather options which tend to be stiffer at first.

Sizes Available: 5-14 | Material: Smooth Calf Leather/Suede Calf Leather | Colors Available: 3

Why they’re great: These Bruno Marc Mesh Oxford Sneakers feature the classic oxford silhouette with a breathable mesh upper. The lightweight EVA outsole is flexible and supportive for plenty of time on your feet. They’re also available with a standard toe design or a wingtip toe design for some added style.

How to wear them: These shoes can be worn with casual outfits and smart-casual outfits. Throw them on with some jeans and a T-shirt or some slacks and a blazer for a more refined look.

Who are these for: These modern oxfords are for someone who wants a classy yet casual shoe to throw on for special occasions. They’re also designed to be worn in warm weather.

Flaws but not dealbreakers: As a low-budget option, it shouldn’t be much of a surprise that these sneakers aren’t made with the highest quality materials. They should likely be reserved for occasional outings but not for everyday wear.

Sizes Available: 6.5-13 | Material: Knit Mesh | Colors Available: 10

Why they’re great: The Steve Madden Fenta Fashion Sneakers feel like a mix between classic derbies and a pair of Vans. These shoes feature a minimalistic silhouette while incorporating a padded interior for continuous comfort. You’re also able to choose between a canvas-style fabric upper and a leather upper depending on your preferences.

How to wear them: These sneakers should feel right at home with a simple, casual outfit. You can rock them with a T-shirt and a pair of jeans or chinos.

Who are these for: These shoes would be a perfect fit for anyone who loves Vans but needs something slightly more sophisticated for certain occasions.

Flaws but not dealbreakers: The rubber sole is the weakest link of these sneakers and is often the first area to begin falling apart. You shouldn’t expect to use these shoes as a daily driver if you want them to last a long time.

Sizes Available: 7-17 | Material: 100% Fabric/Leather  | Colors Available: 8

Why they’re great:  These Cole Haan Zerøgrand Oxfords are some of the most comfortable casual dress shoes you can find. The knit mesh upper offers just the right amount of support and padding while regulating foot temperature as well. The EVA wedge outsole is also designed to support your feet with each and every step, regardless of where you go.

How to wear them: As Cole Haan puts it, these shoes feature a “wear-with-anything” design that makes them perfect for everything from formal to casual. They could be paired with a suit or just a simple button-up and slacks combo.

Who are these for: These shoes are a great option for anyone looking for a casual, yet stylish dress shoe that is, above all, comfortable.

Flaws but not dealbreakers: These shoes aren’t available in wide sizes and the leather tag on the back could cause blisters if worn without socks.

Sizes Available: 6.5-16 | Material: Stretch Knit | Colors Available: 2

Why they’re great: The Monterrey from Tecovas is a rugged yet sleek take on the Venetian loafer. The hybrid outsole incorporates rubber in key areas to provide traction while still featuring a classic leather design. The interior suede heel grip keeps your foot securely locked in place while remaining comfortable, even without socks.

How to wear them: These shoes are a perfect option to wear during warmer months. You can wear them with a pair of tapered chinos, and a polo or button-up shirt.

Who are these for: The Monterrey is great for anyone who wants a familiar, classy shoe to slip on at a moment’s notice. This shoe is also available in an average D width or EE for men with wider feet.

Flaws but not dealbreakers: Size is the trickiest part to nail down with these shoes–they might be too wide or too narrow depending on your feet. Regardless, there are still more sizes available than some other options out there.

Sizes Available: 7-15 | Material: Bovine/Suede | Colors Available: 4

Why they’re great: The Thursday Boots Statesman is a classic derby-style shoe with a touch of ruggedness. The “Army Track” rubber outsoles feature aggressive treading which not only gives these shoes excellent traction, but it makes them more versatile. Everything down to the durable Kevlar laces is built to last daily usage for years to come.

How to wear them: These shoes have a simple design that can be paired with a variety of different outfits. You can throw them on with a pair of chinos and a flannel, or even some dark denim and a jacket.

Who are these for: Whether you’re trying to catch the subway or head to the office, the Statesman is perfect for any daily endeavor–it would also make a great travel shoe.

Flaws but not dealbreakers: Due to the chunky soles, these shoes are relatively heavy if you’re accustomed to sleek dress shoes. Thursday Boots also doesn’t offer any wide sizes at this time.

Sizes Available: 6-16 | Material: Rugged & Resilient Leather/Waxed Horween Leather/Suede | Colors Available: 4

Buying Considerations For Casual Dress Shoes

Shoe Type

The type of casual dress shoe you choose is an undeniably important factor when finding the right choice for you. The most common types are loafers, derbies, and oxfords; however, there’s a whole world of options to choose from. Shoe type determines the kinds of outfits you can pair with your shoes and how frequently you’ll be able to wear them. Each shoe type has its own set of pros and cons, which you can assess depending on your personal preferences.

Material

Material is another big factor to consider when finding the best casual dress shoes for men. While full-grain leather is typically associated with standard dress shoes and boots, it can also serve well in casual dress shoes. Suede is another great option for its naturally laid-back style–it also tends to be more comfortable than many full-grain leather counterparts. Mesh uppers have become increasingly common over the years for their flexibility and breathability. They’re still very on-trend right now and it’s hard to beat the sock-like feeling of these shoes.

Comfort

Comfort is also crucial when throwing on a pair of casual dress shoes because that’s typically the whole point of wearing them in the first place. Many casual dress shoes incorporate modern sneaker technology to maximize comfort and provide a consistent experience. Rubber outsoles and foam insoles have seen plenty of technological development over the years, which goes a long way in creating a cozy environment for your feet to thrive. If you purchase a quality pair of casual dress shoes, they should only get more comfortable with time.

Why You Should Trust Us

As a writer at FashionBeans, I’ve done my fair share of research into men’s attire and style trends. I’ve also been putting these principles into practice for over a decade, trying out different brands and determining what’s best. This is no more true than in the expansive realm of footwear. So, I made sure to include only the very best on this list, narrowing down dozens of options in the process. Hopefully, these recommendations can inform you of what to expect when searching for the best casual dress shoes for men.

Final Verdict

In short, it’s hard to beat The Loafer from Amberjack because of its sheer flexibility. This is a comfortable, modern shoe that evokes the timelessness of classic loafers. On the other hand, the Thursday Boot Company Statesman Shoe is another solid choice to handle everyday life with ease.