How to Wear Boots With Dresses & Skirts (PHOTOS)

Chilly weather is no excuse to give up wearing skirts and dresses with the season's best tall boots, ankle booties, rain boots (as long as it's actually raining), or any boots for that matter. Get out the tights, the leggings, and the thigh highs; it's time to flaunt this great look for cooler weather. We've got some easy pairing tips and lots of super-stylish examples to get you started.

There aren't a lot of rules that go along with wearing boots with skirts or dresses. It's perfectly acceptable to mix and match lots of dress and skirt lengths with all boot heights. And that's good news cause you can't really mess this look up too badly.

Five basic guidelines:

1. Match your boot style with your dress/skirt style: This is sort of obvious but worth considering — try to keep your dress or skirt in the same style range as your boots. In other words, don't wear thick chunky motorcycle boots with a party dress or elegant stiletto-heeled boots with a garden dress.

2. Skirt or dress length: When wearing tall knee-high boots, there should be a few inches of "leg peek" between the top of the boot and the hemline. Same goes for long skirts with mid-calf boots, etc. This is more flattering and less nun-like.

3. Bare legs or not: To go bare legged or not is really a preference. When you're going to work and/or it's cold outside, most women probably prefer to wear tights or leggings with their skirts and boots. However, when your day is casual and the weather is fair, make the choice that works best for you.

4. Have fun with colored or patterned tights. Playing around with tights in great colors or patterns can add a bit of texture or playfulness to your outfit. This is the only time of year you can strut around in tights, so you might as well go with it — and you'll stay warmer, too!

5. Lighten up: We're about to show you some great examples of how to mix and match; however, take care not to drab yourself down with all-dark colors. A black dress atop black tights atop tall black boots is bleck! Too dreary. Lighten up your ensemble with a pale sweater, a colored coat, or tights in a rich color — and don't be afraid to wear brown boots with black or gray.

Here are some great looks that pair boots with dresses or skirts!

Image via Madewell