Dress like a Gentleman.

In every man’s wardrobe there should be at least one pair of sophisticated footwear. Whether it’s for a rare special occasion or for everyday work attire, the foundation of a Gentleman’s style starts with a proper leather dress shoe. That’s why we compiled this list for your consideration before choosing your next outfit.

1. Calvin Klein Jameson Emboss Slip On Loafer




Constructed with 100% black soft leather and a textured upper design, the Calvin Klein Jameson slip on dress loafer for men symbolizes sophistication. Keeping the classic gentleman in mind, this men’s leather shoe was built for comfort and shock absorption with a cushioned foam insole perfect for walking while looking poised.



The seductive and minimal aesthetic of the Jameson leather slip on compliments any casual suit style. Pair this shoe with an off-white slim fitted men’s suit, black loosely buttoned collar shirt and a black pocket square with silver accessories and you have the perfect daywear formal outfit to turn heads as you walk down your local shopping district.

 2. Cole Haan Men’s Williams Captoe II Oxford


 Cole Haan Men's Williams Captoe II Oxford


The Cole Haan men’s Williams Captoe ii Oxford, is constructed with a full leather sole, wheeled welt, rubber base and heel tap on a shoe that’s fully lined with 100% leather, and is usually available in black or British tan colours. Its simplistic and clean design is perfect for any semi-casual gentleman and becomes more distinguished with time.



Wear the British tan captoe Oxford dress shoe for men with a washed blue jean, loosely buttoned collar shirt, tan brown wool waistcoat and matching blazer and walk like a true gentleman down the streets for a day out in town with mates.

 3. Florsheim Men’s Montinero Double Monk Oxford




Cushioned with memory foam technology, the Florsheim men’s Montinero double Monk Oxford is probably one of the most comfortable dress shoes on this list. Constructed with breathable, moisture wicking Suedetec linings and genuine leather uppers you can rest assured that your feet will be taken care of. The sole is also durable and flexible rubber for extra grip while walking.



The Montinero double Monk Oxford dress shoe for men is a popular option for it’s sophisticated design and double buckle finish to add edge to any men’s formal outfit. Pair this shoe with a tan cigarette cut trouser, matching waistcoat, white collar shirt and bow-tie, and bring the look together with a contrasting gray fitted blazer. This look is perfect for the classic gentleman.

 4. Stacy Adams Men’s Dwight Moc-Toe Lace-Up Oxford




Also a very comfortable dress shoe option, the Stacy Adams men’s Dwight Moc-Toe lace-up Oxford with perforated brogue trim and blind eyelet lacing has a memory foam insole for long-lasting support while standing. This shoe compliments any semi-casual styles and works well with dress denim.



Pair the Dwight Moc-Toe Oxford with a slim chino, denim button up shirt and gray wool fitted blazer for a versatile semi-casual daywear Gentleman street look.

5. Stacy Adams Men’s Tinsley Wing-tip Lace-Up Oxford




Constructed with lightweight breathable linings for extended durability, the Stacy Adam’s Men’s Tinsley Wing-tip lace-up Oxford was designed for comfort with memory foam technology. The Wing-tip brogue trims and blind-eyelet lacing is what adds to the classic aesthetic appeal of this dress shoe for men.



Although the Wing-tip dress shoe is generally considered a casual shoe, the Stacy Adams Tinsley proves to be more versatile, complimenting any bold and colourful formal suit outfit. Wear this comfortable pair of men’s dress shoes with a deep violet fitted suit and showcase your daring side at a work conference or formal event.

6. Steve Madden Men’s Jagwar




The Steve Madden Jagwar is a lightweight men’s dress shoe designed to bring out your more playful side. Made of 100% leather and a synthetic sole stitched to a hand finished upper, it is clear the detail on this dress shoe for men is unique and considered an edgy casual foot accessory.



Climb out your comfort zone with a rolled up raw patch tapered jean, waistcoat and blazer layered over a Chinese collar linen shirt for a casual denim look. The Jagwar is all about showcasing your more edgy streetwear style. This statement outfit is perfect for an art festival or a day out in town with friends.

Concluding the Best Leather Dress Shoes for men


It is true that a gentleman should always take pride in his appearance and be dressed to portray his most authentic self. We hope this list steered you in the right direction when choosing your favourite men’s leather dress shoe and that the looks showcased will at least assist with a few ideas on how you can evolve your fashion sense into style Icon status.




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