8 Classic Leather Dress Shoes

Oak Street Bootmakers Bourbon Double Sole Wingtip
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Oak Street Bootmakers Bourbon Double Sole Wingtip

A mid-brown dress shoe will take you far and Oak Street Bootmakers make the right shoe to protect your feet from the ground. The smart broguing throughout, a rubber heel insert, and double leather sole guarantee these will go the distance. When the soles finally kick the bucket, they’ll be ready for a replacement to help them last a lifetime. [$486; oakstreetbootmakers.com

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