6. Cowboy Cowboy boots aren’t just for trips to Texas or costume parties. As far as the trend goes, one season they are in and one season they are out, but if you’re a true fan then your love for your cowboy boots goes deeper than a fashion magazine’s must-have list. The trick to rocking cowboy boots is to balance the country western look with well-structured, stylish pieces. And no matter how you wear them (under your jeans, over leggings, with a dress), keep the rest of your outfit simple.