There are a variety of ways to wear cowboy boots depending on personal style including with a dress, with skinny jeans and with denim shorts. For men, the most popular way to wear cowboy boots is under jeans, or with trousers and a relaxed jacket. Cowboy boots have been incorporated into urban fashion styles, so that they aren't just worn on farms or ranches.
Western boots were originally designed for horseback riding, and still may have features more conducive to riding than everyday wear, including unusual sizing, narrow toes, and a long break-in time. They are best worn casually, rather than to upscale events.