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This distressed chukka-style trading card boot from Kenneth Cole Reaction with dual zippers inject a little edginess, and the block heel and rubber outsole lend cushioning Gives you the practical look and durability. View product details at Amazon

The Frye Company is the oldest continuously operated shoe company in the United States. Founded in 1863 by John A. Frye, a well-to-do shoemaker from England, and family-run until 1945, Frye products have a long and illustrious history. Frye boots were worn by soldiers on both sides of America's Civil War, soldiers in the Spanish-American war, and by Teddy Roosevelt and his Rough Riders. When home-steading drew adventurous New England families to the West during the mid and late 1800's many of the pioneers wore Frye Boots for the long journey. Today Frye remains true to its roots with its line of heritage boots, but continues to innovate as it introduces chic new handbags, pumps, and sandals to its collection. View product details at Amazon

The Frye Company is the oldest continuously operated shoe company in the United States. Founded in 1863 by John A. Frye, a well-to-do shoemaker from England, and family-run until 1945, Frye products have a long and illustrious history. Frye boots were worn by soldiers on both sides of America's Civil War, soldiers in the Spanish-American war, and by Teddy Roosevelt and his Rough Riders. When home-steading drew adventurous New England families to the West during the mid and late 1800's many of the pioneers wore Frye Boots for the long journey. Today Frye remains true to its roots with its line of heritage boots, but continues to innovate as it introduces chic new handbags, pumps, and sandals to its collection. View product details at Amazon

Add some cool texture to your look with the Mark Nason Rebar boot. Lavishly crumple distressed premium leather upper in a dress casual ankle height rocker boot with stitching and overlay accents. Harness overlay straps with metal ring. View product details at Amazon

Pitch a shutout of style with the Mark Nason Nolan boot. Smooth distressed premium leather upper in a side zip dress casual ankle boot with stitching, overlay and metal stud detailing. View product details at Amazon

Pitch a shutout of style with the Mark Nason Nolan boot. Smooth distressed premium leather upper in a side zip dress casual ankle boot with stitching, overlay and metal stud detailing. View product details at Amazon

Pitch a shutout of style with the Mark Nason Nolan boot. Smooth distressed premium leather upper in a side zip dress casual ankle boot with stitching, overlay and metal stud detailing. View product details at Amazon

Ingenuity goes a long way toward compensating for lack of capital, an axiom Kenneth Cole proved back in the early 1980s when he launched his fledgling shoe store out of a borrowed truck parked along a fashionable Midtown Manhattan street. Gaining a parking permit required a clever ruse. Cole added the word "Productions" to his company name, reinvented himself as a film director, hired models as "actors," and got a license to shoot a film appropriately titled The Birth of a Shoe Store. Kenneth Cole Productions, Inc. (the tongue-in-cheek name remains to this day) may not have produced much actual film that day, but it did sell an impressive number of shoes. Today, Kenneth Cole Reaction blends fabulous fashion with functionality, creating urban-inspired footwear for work or play. View product details at Amazon

Kenneth Cole New York is the American designer brand with a conscience. It's the thinking man's brand, a distinction that's more important than ever as today's consumer sees real value in a shared belief system with the brands they support. With Kenneth Cole New York they're empowered to make social statements out of fashion statements. Founded in New York by a New Yorker who has been continually inspired by the energy that is garnered from being a part of the city, New York is in their heritage and future. You don't have to live in New York to be a New Yorker. New Yorkers are people with a New York state of mind. New Yorkers are living in the possibility. This is the embodiment of style: style-conscious enough to create and individuality that feels at home in New York City. Kenneth Cole New York is the New Yorker Brand. View product details at Amazon

Suave style comes roaring back in the Mark Nason De Leo boot. Premium lightly distressed smooth leather upper in an ankle height dress casual rocker boot with stitching accents and contrast leather overlays. View product details at Amazon