Most Comfort Men’s Dress Shoes of 2019

Most Comfort Men’s Dress Shoes of 2019

If you wear dress shoes all day, it may be worth spending a few dollars more for maximum comfort. Even if your day involves a lot of sitting, uncomfortable feet can ruin your mood and your productivity at the same time. Whether you’re looking for shoes for the office or for a social event, these Most Comfort Men’s Dress Shoes should treat your feet right.

Read: Men’s Dress Codes Guide For All Occasions

Before you make your selection; it’s best to take a few minutes to consider what is important in a dress shoe.

Here are a few criteria to keep in mind when shopping For Most Comfort Men’s Dress Shoes.


This should always be priority number one. Consider the sole, cushion, and other comfort factors.


Some men prefer penny loafers; others prefer a classic wingtip or oxford. There is no right or wrong, this is just your personal preference. Any classic men’s dress shoe style will do.


Leather shoes are the standard for men’s dress shoes, though you can find some styles in other materials, like suede.


Some cheaply-made shoes fall apart quickly while high-quality shoes can last for years or even decades when re-soled. Consider that before springing for the most inexpensive option.


When it comes to price, you have some flexibility. Browsing online shoe listings yields pairs below $20 and over $1,000. But you probably won’t find anything very good for less than $30. In the $40-$60 range, you will find some shoes that are wearable, comfortable, and stylish. But they likely won’t hold up for the long-term. The $60-$80 price range yields higher-quality shoes that should withstand regular wear and offer a balance between good value and high quality. And from $80-$120, you are getting into the lower tier of premium shoes. Here you should be able to find great shoes that last a long time; fit comfortably, and look good with classic styles.

While you can easily spend more than $120 on dress shoes, don’t feel like you have to. But if you are willing to stretch the budget; premium brands like Allen Edmonds bring the most comfort and quality you can get in a shoe. Depending on your needs and budget; you should be able to find a good shoe that fits your needs without overspending.

Brand name matters some of the time, but not always. Sure, you can spend a lot more on designer shoes, but in most cases, people won’t notice the label. Focus on the core qualities above and you should get the best results.

Most Comfort Men’s Dress Shoes

Read on for our selections of the Most Comfort Men’s Dress Shoes available online.

Best Overall: Allen Edmonds Men’s Carlyle Oxford


$395 BUY NOW

The Allen Edmonds Carlyle Oxford is the best overall dress shoe for men. Allen Edmonds is a company with roots going back to 1922 and offers some of the finest dress shoes in the world. The Men’s Carlyle Oxford is a class style with a plain, attractive finish.

The leather dress shoes set a high bar for comfort. The high-quality shoes should last for years even with daily wear. But they are pricey, so it is good to take good care of them to make them last.

With some things, you get what you pay for. That is the case with these ultra-high-quality dress shoes. These shoes generally run in the $300+ price range, so prepare for a little sticker shock if you’ve never looked at high-end dress shoes before. But if you try them on, you won’t ever want to go back.

Best Budget: Florsheim Men’s Montinaro Wingtip Dress Shoe Lace-up Oxford

Florsheim Men’s Montinaro Wingtip Dress Shoe Lace up Oxford



Florsheim is a great choice for budget dress shoes as they’re typically below $100. The Montinaro Wingtips come in black, tan, chocolate, and brown and feature a leather upper, synthetic sole, and hand-antiqued style details that show off the traditional wingtip features like the medallion toe.

The memory foam insole won’t hold up as well as traditional leather soles, so they are better for occasional use for dressy functions rather than daily wear.

Best Value: Cole Haan Men’s Lenox Hill Cap Oxford

Cole Haan Men’s Lenox Hill Cap Oxford


If you want a classic, well-made shoe without the high price tag of some luxury brands, the Cole Haan Oxford is the way to go. In the $100 price range, these shoes bring both high quality and great value. Cole Haan shoes also have a great reputation for long-lasting durability.

This lace-up leather shoe comes in tan, black, and brown color options. The soles are rubber with 1.25-inch heels. With these, you will look great, your feet will feel great, and you won’t break the bank.

Best for Comfort: Cole Haan Men’s Pinch Tassel Loafer

Cole Haan Men’s Pinch Tassel Loafer


Cole Haan’s slip-on loafers set a high standard for comfort and quality. If you want a slip-on dress shoe, you can’t go wrong with Cole Haan. The Men’s Pinch Tassel Loafer is one of the most popular tasseled dress shoes available today.

This reasonably priced shoe offers great value. It is made of leather with a combination of leather and rubber sole. It has a one-inch heel and moccasin-style toes that offer maximum comfort for long days on your feet or at your desk.

Best for Casual Events: Sperry Top-Sider Original Boat Shoes

Sperry Top-Sider Original Boat Shoes


These Sperrys set the standard for boat shoes, and are a trendy choice for brunch, afternoon drinks, or any casual gathering. They come with a competitive price tag and high-quality build. The shoes are all leather with a non-marking rubber outsole. Those are useful features for boating, but you can enjoy these shoes just as well on land.

The shoes feature a beveled heel, rawhide laces with rustproof eyelets, and slip-resistant soles. They are hand-sewn for the best quality finish. However, beware that some recent reviews indicate quality is not what it once was.

Best for Formal Events: Stacy Adams Gala Lace-up Oxford


Stacy Adams Gala Lace-up Oxford



You probably don’t wear your most formal shoes all that often, so it’s okay to save a few dollars here. The Stacy Adams tuxedo shoe looks great and is still affordable. It comes in black, white, red, navy, and gray. The patent finish will shine just like a shoe that costs 10x as much.

These handmade shoes have a synthetic sole and lace up the front. They use a lightweight construction that won’t weigh you down after a long wedding or business function. They combine a classic look with a bargain price but don’t be surprised if they don’t hold up as well as a more expensive pair.

Best Slip-On: Allen Edmonds Men’s Cavanaugh Penny Loafer

Most Comfort Men's Dress Shoes Cavanaugh Penny Loafer

BUY NOW $222

Allen Edmonds is making a second appearance on this list thanks to its ultra-comfortable, high-quality Cavanaugh Penny Loafers. If you enjoy the penny loafer look, this slip-on pair comes in walnut, black, and brown colors to best match your wardrobe.

These loafers are leather with a leather sole and stacked heel. Made in Wisconsin, USA, this shoe combines the classic style with contemporary designs to make it an effortless addition to any man’s shoe rack.

The penny loafer look works well with a suit, sportcoat, jeans, and just about any other style from casual to formal suit-and-tie occasions. With Allen Edmonds, you can’t go wrong.

Runner-Up, Best Slip-On: Steve Madden Men’s Dwellr Slip-on Loafer

Most Comfort Men's Dress Shoes Steve Madden Men's Dwellr Slip-On Loafer



Steve Madden is a well-known brand for both men’s and women’s shoes. Their slip-on loafers offer a simple elegance that is great for the office or social functions, and they work well with dress pants to dress up or jeans to keep it casual.

Steve Madden dress shoes are reasonably priced and offer a good value for the cost. You can count on a comfortable sole and high-quality stitching. They won’t last forever, but at this price point, you won’t mind replacing them once in a while.

Best Statement: Calvin Klein Men’s Atlee Ballistic Nylon Oxford

Most Comfort Men's Dress Shoes Calvin Klein Men’s Atlee Ballistic Nylon Oxford



These bright red Oxfords (they come in more neutral colors, too) make a statement the moment you walk in the room. These shoes are made of nylon with a synthetic, flexible rubber sole, and add a tasteful pop of color to any outfit.

The classic lace-up shoes also come in navy, black, gray, and toffee colors, all of which are generally work-appropriate and stylish. They are super lightweight and can handle both a day in the office and a night on the dance floor. Add a little flair to your daily wardrobe with something that goes beyond classic brown leather.