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

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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, I don't have time to deal with blisters from breaking in new kicks. My morning commute to the city involves about 30 minutes of walking and even more time standing on a packed Metro, so I figured it was the perfect time to put these shoes to the test.

With heat-activated arch support, Amberjack shoes start forming to your feet from the first wear. I thought they were comfortable straight out of the box. The dual-density TPU outsole feels like a sneaker, but the sheepskin interior is incredibly soft and buttery. I gotta say- it's no wonder that these shoes were named the Most Comfortable Dress Shoe by Men's Health! 

The ZERØGRAND Wingtip Oxfords from Cole Haan use a leather upper with a FlowerFoam EVA midsole that provides lightweight cushioning and flexibility. These guys were comfortable too - but the sole felt a little flimsy. I'm not sure if these can hold up long-term with my commute. They're made to reduce heel friction and add extra wiggle room in the toe. They offer a medium and wide width, which was great to find 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 accommodate.

Winner: Amberjack

Style

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 colorways. With 13 different combinations of color and material, you're bound to find your perfect pair. Even with the innovative comfort technology, Amberjack looks the most versatile and sticks to a classic dress shoe silhouette. I thought these looked great with a suit and even with jeans and a henley for a post-work happy hour. 

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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. I didn't like the contrast of the thick rubber sole with the sophisticated leather upper. I've seen these referred to as "clown shoes" on Reddit, but figured I would give them a chance if the comfort was great enough. While they offer slightly more support, I'm not running a marathon in them, and 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. The sole of these makes them definitely look more like a sneaker, but I still think they're a good fit for a casual Friday or a nice date night.

Winner: Amberjack

Price

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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. Amberjack and Cole Haan both produce their shoes in Portugal, but the ZERØGRAND Wingtip Oxfords will put you out $220. At $289, the Crossover™ Longwing is the most expensive. 

Winner: Amberjack

Final Thoughts

OUR TOP PICK

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AMBERJACK

The Original

OUR RATING

★★★★★

4.9

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.

SHOP NOW

If you're looking for the best value with optimal comfort, a wide range of styles, and versatility, look no further than Amberjack. I wanted the look of a dress shoe with the comfort of a pair of sneakers and that's what I got with 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.