My girlies, lets talk proportions because this mistake is too common., Wearing midi dresses with ankle boots creates an awkward gap, breaks your silhouette, and shortens your legs. We wouldnt be 15 Shoes We're Wearing With Our Coziest Sweater Dresses This Fall Wearing Ankle Boots with Dresses Over 40 Complete Styling Guide The Monroe Dress Black Modest Ankle Length Dress with V Line Waist Ianna Collection What Style of Dress Goes Best with Ankle Boots? Essential Style Boutique Finding the Perfect Length: Short, Midi, Ankle Length, or Gown? Adrianna Papell