The Rocker/Biker Boot - Do slide on with the shortest hemline you can muster, with leggings to show off the boots. Skinny jeans also hit the mark for a complete rocker chic ensemble. Goodman advises not pairing these chic boots with wide-leg trousers, which give too much of a clunky feel on the bottom half.
The Equestrian/Riding Boot - Do slide on this classic favorite with leggings and other tailored pants that are tucked into the boot. Also wear with short skirts paired with leggings. Don't pair with wide-leg pants or three-quarter-length skirts or dresses, as they look frumpy with flat boots.
The Western Boot - Do slide on with all types of denim (tucked or untucked), long skirts, floral printed frocks, any casual look to rope in the cool factor. Don't pair with other Western pieces - the goal is not to look like an actual cowgirl. Whoopee!
Professor Discusses 1 Tip To Match 5 Winning Numbers.