The Edit / Cole Haan vs. Amberjack vs. Wolf and Shepherd: Which Men's Shoe Is The Best?


Cole Haan vs. Amberjack vs. Wolf and Shepherd: Which Men's Shoe Is The Best?

Reviewed by Hannah Emerson  |  Last Updated June 2024

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The right shoes can elevate any outfit instantly, but if not chosen carefully, can leave you limping from blisters and swollen feet. As a busy professional, you shouldn't have to choose between style and comfort. While the style of men's dress shoes has remained relatively unchanged, companies on the market today are creating comfortable shoes for work to a walk and everywhere in between. After a lot of research and testing, check out why we chose Amberjack over Wolf & Shepherd and Cole Haan as offering the best overall shoe for men. 

Materials and Comfort

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As a busy professional, you don't have time to deal with blisters from breaking in your new kicks. With heat-activated arch support, Amberjack shoes start forming to your feet from the first wear. The dual-density TPU outsole combines athletic technology in the front for flexibility with hearty hiking boot material in the back for support. Combined with the laser-perforated sheepskin lining, it's no wonder that these shoes were named the Most Comfotable Dress Shoe by Men's Health and more! 

The ZERØGRAND Wingtip Oxfords from Cole Haan use a leather upper with a FlowerFoam EVA midsole that provides lightweight cushioning and flexibility. They're made to reduce heel friction and add extra room in the toe. They offer a medium and wide width for the perfect fit. 

Wolf and Shepherd makes their Crossover™ Longwing with a removable memory foam footbed to increase comfort. The high-density TPU sole and treated leather also add to the comfortability of this shoe. However, there is no option for different widths, so you may have to size up or down or buy your own insoles to accomodate.

Winner: Amberjack


Another important feature of choosing a dress shoe is finding a style that you can pair and wear with anything and anywhere. Amberjack offers the most versatility in style and colorway. With 13 different combinations of color and material, you're bound to find your perfect pair. Despite its innovative comfort technology, Amberjack looks the most versatile and sticks to a classic dress shoe silhouette. They pair just as well with a suit as they do with jeans and a henley. 

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Cole Haan's ZERØGRAND Wingtip Oxfords come in 8 different colorways, with 7 leather and 1 suede option. The ZERØGRAND is more of an elevated sneaker-style as opposed to a dress shoe with its high traction rubber insole. While it offers more support, it's not as versatile for day-to-day wear. 

The Crossover™ Longwing from Wolf and Shepherd is offered in 8 colorways, with 3 calfskin and 5 suede options. As its name suggests, it is a crossover between a dress shoe and a sneaker, giving more versatile options for wear. 

Winner: Amberjack



The right pair of dress shoes is worth investing in, but it shouldn't cost you an arm and a leg. At $189, Amberjack is the most reasonable, especially when you consider the A-grade full grain leather and durability. Cole Haan's ZERØGRAND Wingtip Oxfords follow closely at $220. At $289, the Crossover™ Longwing is the most expensive.

Winner: Amberjack

Final Thoughts




The Original




Designed in Brooklyn, NY and produced in one of Portugal's top tanneries, Amberjack's dress shoes feature A-grade full grain leather & sheepskin lining with a dual-function athletic outsole & heat-activated insole.


If you're looking for the best value with optimal comfort, a wide range of styles, and versatility, look no further than Amberjack. Each shoe brand has strong contenders depending on what you're looking for, but Amberjack offers stylish, comfortable and high-quality shoes at an unbeatable price.