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Best Steve Madden Dress Shoes: Chic, Cool & Affordable

Casual fashion may be the height of style today, but there will always be an occasion for a stylish pair of dress shoes. 

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Our Top Eight Steve Madden Dress Shoes

When that time comes, reach for one of these best Steve Madden dress shoes for a chic and affordable option for your formal wardrobe.

Steve Madden Men's Harken Chukka Boot

Best For Versatility

The Steve Madden Men's Harken Chukka Boot features two or three sets of eyelets, making it the perfect example of a chukka boot. The Harken boot comes in three attractive colors, including a head-turning Steven Madden dress shoe brown tweed option.

PROS: This shoe is made of 100 percent genuine leather. The Harken boot will continue to become more comfortable and will mold to your foot and age well over time.

CONS: Chukkas can be a difficult style to wear and this particular style can be tight at the toes for wearers with wider feet.

  • Fit: Sizing is better for those with narrow feet and the shoes tend to run slightly large. 
  • Comfort: Once these shoes are broken in, fans rave about the comfort and ease of these Steve Madden dress shoe slip-ons.
  • Durability: Devotees claim they never retire these chukka boots and instead demote them for more casual purposes once they’ve worn them for a while. 
  • Value: Men’s dress shoes in 100 percent leather can come at a premium price, but these long-lasting shoes are a good value. 

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Steve Madden Men's Harpoon Oxford Shoes

Best For a Classic Look

The Harpoon Oxford Steve Madden dress shoe offers a no-nonsense option. An oxford shoe represents the signature silhouette for traditional men’s formal footwear.

PROS: This pair comes in two gorgeous shades of brown, a traditional medium-tone tan color and deep, red-brown color called Wood. 

CONS: It may take some trial and error to find a shoe that fits perfectly, including outside of your standard shoe size.

  • Fit: Steve Madden offers this dress shoe in extended men’s sizes, from 14 to 17.
  • Comfort: A solid rubber sole helps ground this signature shoe and provides additional comfort and safety when walking in slippery or wet environments. 
  • Durability: These shoes are also all-leather and boast a long life. The patina will wear nicely and evolve with age.
  • Value: This versatile shoe carries you effortlessly to formal occasions like a wedding or graduation or a more casual weekend dinner date. 

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Men's Yorkk Loafer - Best Steve Madden Dress Shoes

Best For Comfort

If you are looking for a sturdy walking dress shoe, the Steve Madden Men's Yorkk Loafer provides comfort and classic style. 

PROS: Those who need a slip-on shoe can still show up in style with the Yorkk Loafer from Steve Madden.

CONS: This style of shoe is notorious for its narrow shape. A loafer style may not work for you if you have a wider foot or high instep.

  • Fit: This narrow loafer fits some feet well, particularly narrow feet with a low or medium instep.
  • Comfort: Loafers provide one of the most comfortable options for a men’s dress shoe. This slip-on style promotes effortless sophistication for men’s dress shoe shoppers of any age.
  • Durability: The rugged sole of this loafer elevates this shoe from getting too close to bedroom slipper territory. 
  • Value: A more casual, slip-on style, this loafer ranks as one of the more affordable types of men’s dress shoes available.

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Steve Madden Men's Hestonn Shoes

Best For a Shoe Enthusiast

The Steve Madden Men's Hestonn dress shoe looks like many of the men’s formal footwear options you may see on the street today. However, with its durable leather and classic style, this shoe is a wardrobe staple. 

PROS: This chukka boot is versatile, trendy, and long-lasting. Many devotees purchase pair after pair of these Steve Madden men’s dress shoes.

CONS: The Hestonn shoe does not come in any Steven Madden dress shoe black or dark shade, but does have three shades of brown.

  • Fit: The chukka style can be narrow in the toe box and some experience discomfort with a high-top style of boot. 
  • Comfort: Many wearers claim to wear these shoes constantly and replace them when needed. The leather construction molds to the wearer’s foot for a bespoke footwear feeling.
  • Durability: The Tobacco Suede version of this boot requires special suede care to maintain its color and stability. 
  • Value: The long-wearing nature and versatility of these men’s dress shoes present a strong value for these men’s dress shoes.

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Steve Madden Men's Jagwar

Best For a Rugged Look

The Steve Madden Men's Jagwar offers a unique and fashionable alternative men’s dress shoe. 

PROS: The unique color design features a darker toe and heel for a contemporary appearance.

CONS: There is only one color available for the Jagwar oxford shoe.

  • Fit: Classic oxford shoes normally fit true to size. This dependable men’s dress shoe offers a standard fit you can count on, without the traditional challenges of wide or narrow feet.
  • Comfort: Like most men’s dress shoes, consider breaking in these shoes before trusting them for a long duration of wear.
  • Durability: Another 100 percent leather shoe, this shoe will last for years and evolve to fit you better each time.
  • Value: Because of its unique appearance and limited colors, this men’s dress shoe offers less versatility for the money.

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Steve Madden Men's Nunan Oxford

Best For a Basic Dress Shoe

The Steve Madden Men's Nunan Oxford strikes a sophisticated profile in any setting.

PROS: These sturdy and attractive men’s dress shoes offer a sleek option for formal dressing.

CONS: This pair of Steve Madden men's dress shoes in black features a dark brown sole, which may not look the best with some formal wear.

  • Fit: Shoppers can rely on the dependable fit of a basic oxford shoe. Beware of a narrow-toe box.
  • Comfort: This classic dress shoe ranks lower in ease than a chukka boot or loafer but is still reliable footwear for a long, formal occasion.
  • Durability: The Nunan Oxford shoe comes with a thick sole, offering considerable durability for these men’s dress shoes. 
  • Value: These Steve Madden dress shoes are not leather but still have a comparable price tag to the 100 percent leather shoes on this list.

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Steve Madden Men's Covet Monk-Strap Loafer

Best For a Fashion Statement

The Steve Madden Men's Covet Monk-Strap Loafer delivers the dapper choice on this list. Spice up your formal wear with these fashion-forward shoes. This is not your grandpa’s loafer!

PROS: An unusual style of shoe with additional comfort. 

CONS: While considered a loafer, these shoes are not slip-on. The strap may make these shoes inaccessible to some.

  • Fit: An adjustable strap across the top of the shoe makes this monk strap style comfortable for a wide range of feet.
  • Comfort: This is one of the first shoes on the list with a solid square heel, which can be a deterrent to some. 
  • Durability: The Covet Monk-Strap Loafers come in 100 percent leather and a protective cap toe. Plan to wear these versatile and attractive shoes in all weather.
  • Value: Because of the high-fashion appearance of these shoes, they rank as the most expensive Steve Madden dress shoes on this list.

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Steve Madden Men's Kramdin Bit Loafer

Best For a 90s Throwback

These Kramdin Bit Loafers pair perfectly with a preppy 90s ensemble, making them a great option for a blast from the past.

PROS: These chunky and comfortable shoes effortlessly hold wide and narrow feet.

CONS: As many people wear these without socks, these shoes can generate an odor.

  • Fit: These 100 percent leather shoes will stretch to fit most feet. The thick sole makes these comfortable walking shoes.
  • Comfort: Kramdin Bit Loafers offer a simple, slip-on style that highly prioritizes comfort. 
  • Durability: The thick rubber sole can start to degrade, especially with heavy use. 
  • Value: Like the monk-strap loafers, these fashion-forward men’s dress shoes carry a slightly higher price tag.

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About Steve Madden

Steve Madden Outlet

Steve Madden is an American shoe and accessories manufacturer best known for making affordable versions of the trendiest, most fashion-forward footwear. 

What To Wear with Steve Madden’s Dress Shoes

Steve Madden dress shoes represent a wide spectrum of styles to fit any outfit.

Pair some Steve Madden oxford dress shoes with a classic suit or tuxedo look for a traditional appearance.

Or mix in Madden’s signature array of loafers for a fashionable spin on your favorite look.

Final Thoughts

Steve Madden shoes deliver fashion and accessibility in a variety of classic styles with a fashionable twist. Try Steve Madden men’s dress shoes for all of your special occasions.

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Steve Madden Shoes
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Born and raised in Austin, David is a dedicated writer and avid fragrance lover. When he's not trying out perfumes, he enjoys traveling and exploring new restaurants.