Wearing cowboy boots with a dress or skirt is one of the trickier looks to pull off, but it can work for women over 40. Opt for bare legs with a clean-lined skirt (like Allison Janney is wearing) or add tights (like Sara Nodjoumi has done.) Avoid wearing cowboy boots with anything ruffled or tiered or you'll look like you just stepped off the set of "Hee Haw."