Stop Short!

Sienna Miller leaving a restaurant in New York City last year.
Left to Right: Maxine Shoe by Scorah Pattullo, $543.12, www.my-wardrobe.com; Kadee, $119.99, Aldo; 'Rosetta' Ankle Boot by Report Signature, $172.95, Nordstorm; Tie Front Suede Shoe Boot, $90.00, www.asos.com
Left to Right: N-Trigue, $199.95, Steve Madden; Lucinda, $129.99, Aldo; Softly, $140.00, www.faith.co.uk; Roundabout Booties, $428.00, Anthropologie

I’ve always thought ankle boots were awkward - they seem to just 'stop short'. How do you wear them?.. Under jeans? Over pants? With skirts? I have a cream colored pair that I only wear under my jeans, but I’d like to experiment and try wearing them tucked into a pair of slightly boot cut jeans a la Sienna Miller (pictured above). Team with a chunky belt and lots of layers to give you the ultimate summer-to-fall look!