What to Wear with Ankle Boots for Women Ankle Boots with Long Skirts. Whether they're flat or heeled, ankle boots and long skirts or maxi skirts are classic combinations for fall. Short Skirts and Ankle Boots. ... The Best Pants for Ankle Boots. ... Ankle Boots With Leggings or Tights. ... Clothes to Avoid Wearing With Ankle Boots. ...How should my boots fit?
A person should check the fit of leather boots while standing. A leather boot should make the entire foot feel snug except for the heel. The ball of the foot should sit at the widest part of the sole of the boot. The instep, or vamp, of the boot should fit more snugly over the top of the arch than a normal shoe or sneaker.