Here is a quick lil rundown on How-to: 'Wear Ankle Boots'
Pick out your ankle boots. Darker colors will work best, and you can never go wrong with black. Slouchy, flat ankle boots with a round toe will create a cute, younger hipster look. Short cowboy styles with a pointier toe and a very low heel will create a more urban, sleek vibe. For a foxy fashionista look, go for pointy, high-heeled styles.
Pair your boots with the right skinny jeans. Do not choose jeans with a waistband that is so tight, your skin bulges over the top. (Go up a size if you have to.) A higher-waisted skinny jean can be very flattering.
Choose the right shirt. Skinny jeans and flat, slouchy boots look best with a tunic or a longer, billowy shirt.
For a more urban, edgy look, pair the sleek, cowboy-inspired ankle boots with modified vintage T-shirts and vests, short leather jackets or vintage-look blazers.
Stick with classic black, white, silver and gold if you're wearing high-heeled ankle boots. Think super-trendy, and look for belted tunics and off-the-shoulder tops/sweaters.
Here are a few 'Ankle Boot looks' that I love...Enjoy!!
(Info and images found on Pinterest.com & Google.com)