The events that require dress shoes – cocktail parties, wedding receptions, your job – can drag on, and not all brogues are particularly kind to men's feet. That's why it's so important to find a shoe that's primarily built for comfort then wrapped in a sophisticated leather shell. Tsubo's Winslow II boots, the ultimate commodious wafflestomper, will not only keep your dogs from barking but provide them with a slick, modern doghouse.

The folks over at Tsubo constructed the Winslow with a polyurethane cushioned footbed, a shock absorption pad for the heel, and a flexible, removable sock liner in order to create an incredibly comfortable, high-top–style boot. Not content to pad the interior, they cut perforations in the leather outer for air circulation and rounded the edges of the sole. Luckily, the designers weren't content with simulating the feel of a sneaker and continued building an original dress boot.

The Winslow II's tanned, rigid base gives way to the smooth leather and rubber outer shell, decorated with a Western-inspired pattern of perforations. The precision-cut arches and practically seamless stitching evidence a rigorous emphasis on craftsmanship. A thick leather strap wraps around the back of the shoe and has an eyehole on either side that the laces weave through midway up for added foot stability and a unique urban cowboy-in-spurs look.

We found the Winslow II to be eminently wearable, not only because they so delicately cradled our feet, but also because they look good with both jeans and dress pants. These shoes even have an elastic element in the ankle to make putting them on in the morning and taking them off at the end of a long day as easy as possible. [$240; tsubo.com]