When talking about statement shoes and boots for guys, it's all about authenticity. Founded in 1863, Frye is the oldest operating shoe company in the United States, and that rich history comes through in each shoe and each boot they make. Worn by Civil War soldiers and WWII servicemen, Frye knows a thing or two about sturdy construction, comfort and functionality.

The equestrian inspired Jayden Chelsea Boots are a must-have! Round toe with cushioned shock-absorbing leather insoles and leather lining with stacked leather heel and durable Goodyear welt construction, this boot was made to last! The belted harness strap and antique brass hardware add attitude and edge. This boot will just get better with age!

Another boot that'll get even better with age is the Heath Outside Zip Boots. Taller and more casual, but just as tough, the distressed waxy suede with sturdy squared toe and cushioned shock-absorbing leather insole make for a comfy everyday boot that you'll break in fast!