Shoes to wear with bootcut and flared pants

Q. Although I have embraced the skinny jean trend, I have to admit that I still can’t resist bootcuts and flares. I usually wear them with ballet flats in the spring and fall. I would love to wear flares and bootcuts in the winter but I am at a loss for what to wear on my feet. I have heard high-heeled round toe shoes but I find that impractical and hard when chasing my two-year-old and walking through the ice and snow. Do you have any suggestions?


A. My favorite styles to wear with bootcut and flared jeans and pants in cooler weather are ankle boots. Heeled styles are perfect for when you want a polished look, but a flat ankle boot, or chelsea boot, is great for when you want a casual, comfortable look. If you’re wearing in the ice and snow, you’ll want a boot with a rugged sole. And for evenings out when you’re not chasing around your two-year-old, a pump (round or pointed toe) will give you a dressier look.

Here are some casual boot options to wear with your bootcut pants with a lower, more comfortable, heel:

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