Shorts
Right — shorts aren't normally considered pants, but they're technically just extremely short pants. When you're ready to rock a pair of ankle boots with a pair of shorts but you feel hesitant, throw your worries out the window and go for it. In warmer weather, pull on a cream-hued, lightweight crocheted sweater over moss green corduroy shorts and black suede, chunky-heel ankle boots. In cool weather, wear the same outfit, but pull on a heather gray, thin layering T-shirt under the sweater, black opaque tights under the shorts and a black coat over the entire look — so versatile.
Long and Stacked
When you're wearing a pair of skinnies with ankle boots, unlike a wider-leg silhouette, you don't have to worry too much about tailoring when it comes to length. Even way-too-long-for-you jeans will stack over your boots or inside of them if there's room to tuck them in — both add a chic bit of visual interest to your ensemble. Think black oversize, boxy cowl neck sweater over long, dark blue skinny jeans. Stack your pant legs over taupe ankle boots with cone heels. It's that easy.
To the Boot Top
If visiting your tailor with a new pair of pants is a common occurrence in your life, this one's a cinch. Head to your tailor with your pants and your boots. When you try the pants on for the tailor, pull your boots on, too, and ask for a hem that falls to the very top of your boot if you're not a fan of a stacked pant leg. Visualize yourself in slim-leg charcoal jeans that fall to the top of light gray, flat ankle boots. Pull on a white tunic shirt with a button-down placket for a casual, chic vibe.
Cropped
You want to wear your boyfriend pants with ankle boots, but how high do you roll them? Just because your boots are cropped doesn't mean you can't wear a cropped pant, too. Envision yourself in a pair of olive green boyfriend-style cargo pants. Step into dark brown, high-heel ankle boots and roll your pants up 1or 2 inches above the tops of your boots. Throw on a slouchy navy blouse with an all-over tiny-floral print and tuck the very front into your pants, blousing it out.
