The T+L team tested nearly two dozen pairs of men’s dress shoes, wearing them at least three times, and testing for out-of-the-box wear, two-hour wear, and all-day wear. But all in all, these are a solid and reliable option in a highly flexible style. There were no hot spots or blisters after several hours of wear, but we did feel that these are more geared toward an occasional special event, noting that guys who wear dress shoes every day might gravitate toward something a little more casual like a penny loafer. While we didn’t find this shoe exactly form-fitting out of the box, it didn’t feel overly stiff. It has the look of a dress shoe but the feel of something much more easygoing.

We especially loved that this City Tray derby is built with Fluidform Direct Comfort Technology, a type of comfortable-yet-supportive sole that’s lightweight and plush while still feeling anatomically supportive. Dress it up, dress it down, wear it to work, wear it to a wedding - this shoe can go everywhere. The heel might feel a little formal for some men.Ī plain-toe derby is one of the most versatile shoes a man can buy. The Details: 7 to 15 | Leather upper, rubber sole The brogue detailing lends a heritage feel, and the grooved rubber sole offers a distinctively modern approach to a classic silhouette. They’re also, simply put, a beautiful pair of shoes. A removable cushioned insole adds even more comfort.

Our reviewer was able to wear them all day long and feel their back was supported, too. But a little bit of support goes a long way and still secured the top spot for this pair of shoes. The only area where this shoe lost a fraction of a point was for the comfort rating - because the rubber sneaker sole has a slight degree of support instead of just pure marshmallowy bounce back. Our reviewer appreciated the quality of the leather uppers and herringbone stitching, and admired the comfortable but supportive fit. These Cole Haan classics are a best seller for a reason: they have a buttery smooth, yet supportive fit right out of the box, and are equally as pleasant for short strolls as they are for long walks. The sneaker sole may read a little casual for some workplaces.Ĭole Haan has been synonymous with quality, craftsmanship, and excellent shoemaking for nearly 100 years.

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