Wolf & Shepherd Toro Striker Chukka Boot, $365Size 8See last pic for small imperfection The Wolf & Shepherd Striker takes a traditional Chukka boot style and elevates it with sleek elongated toe box and hand-burnished accents on the toe and heel. The high top design makes it the perfect shoe for fall.Made in PortugalSuggested size 1/2 up Founded by former Adidas designer Justin Schneider, Wolf & Shepherd is a men's dress shoe startup that provides sneaker-like performance and comfort using innovative technologies.To put their comfort to the test, Schneider wore a pair of his dress shoes to participate in the Running of the Bulls in Spain.The sneaker-like performance and comfort Wolf & Shepherd stands by aren't just baseless claims or hyperbole for padded insoles; there is real innovation behind it. On the outside, Wolf & Shepherd's designs look like premium men's dress shoes, but on the inside you'll find soft sheepskin linings, plush memory foam insoles, a carbon fiber shank for stability and weight reduction, an HDeva heel, laser-cut rubber outsoles.With most pairs priced between $300 and $400, Wolf & Shepherd shoes are expensive, but well worth it. Sure, you can catch a pair of modern wingtips made from a breathable knit material if you're going after comfort, but they'll never be as sleek as a pair of these shoes. They are the perfect balance of classy dress shoe with all the performance necessary for commuting and staying on your toes in the work environment.