Cowboy Boots have found a home off the range, and cap-toe clodhoppers, military lace-ups and ankle-high Chelsea styles are showing up where only brogues, wing tips and slip-ons once trod. In fact, boots are being worn with just about everything from dinner jackets to baggy denim shorts. (Troy Aikman wore black leather cowboy boots with a tuxedo in our Quarterback Chic fashion feature last month.) But whatever the look, take time to find a pair of boots that really fits. For maximum comfort, your heel should move up and down slightly in the back, and the boot's interior should be smooth and seamless. And if rugged workman-style boots work best for you, make sure that they're fully waterproof.
Our guy's well-shod wardrobe includes the calfskin cowboy boots, by Attitude for Pop Cowboy, $275, that he's wearing, plus (from left to right) leather military boots with rubber lug soles, by Georgia Boot, about $100; nubuck waterproof hiking boots with cushioned insoles, by Dexter, $110; mat leather, double monk-strap chukka boots with lug soles, by Kenneth Cole, $154; calfskin cap-toe boots, by Impulse for Steeplegate, $115; oily nubuck engineer boots with buckle straps, by Dingo, $125; and suede Chelsea boots with elastic side panels, by Paul Smith, $235.