Boots are hard to wear well- it’s easy to misstep on the road to boot aplomb. But don’t worry- here are the two boot rules that will help you step out in style, regardless of shaft height.
1. There should never be a gap between your leg and the top of the boot. Make sure the boot shaft (the part on your leg) is comfortable, but snug. (Galoshes are the only boots that should gap. And if you’re tempted to ask about Uggs, don’t- there is a reason their name sounds like UGHH.)
2. Wear tights!!! If it’s cold enough to wear boots with a skirt, it’s cold enough for tights. Tights help blend the boot into the rest of your outfit so people notice you and not just your shoes.
Kenneth Cole
The fine line between ‘School Marm’ and ‘Sexy Librarian’ is your waist. If you wear short boots with a skirt or dress, make sure you’ve defined your waist with a belt or fitted jacket. Or, channel Bonnie Parker and rock them with wide legged trousers and the confidence of an outlaw.
Steve Madden
Mid-calf is the most flattering and versatile height. It’s easy to wear with pants and great with skirts. You’ll have enough leg showing above the boot to be able to wear a skirt at any length.
Eddie Bauer
Here’s the painful truth: Tall boots make most women (even leggy women) look stumpy. And they direct everyone’s attention to your knees. If you wear them, make sure your skirt hem falls at least three inches below the top of the boot.