Dear VienneMilano,
I recently purchased a cute pair of ankle boots. While I love the style, I'm not sure what to pair the boots with. How can I incorporate ankle boots with stockings for work?

Briana C.

Thigh boots, cowboy boots, or ankle boots - boots are generally a fabulous complement to hosiery. To start, the three things to consider when pairing boots and tights are:

  • The Occasion – Typically, boots are not appropriate for formal occasions (with exceptions, of course). Instead, boots are ideal for work, parties, hanging out with friends, and night out in town.
  • The weather – What's the temperature outside? For warm summer days, give fishnet stockings and ankle boots a try. For cold winter days, try pairing thick stockings (55 deniers and up) with your boots.
  • The Outfit – Dresses, skirts, and pants are all fashionable items that can be paired with hosiery and ankle boots. For cold winter days, thigh highs can be worn underneath your pants for warmth.

The Do's and Don'ts of wearing ankle boots with stockings:


  • Do wear ankle boots that match the color of your stockings - otherwise, your outfit may get a bit overwhelming.
  • Do wear fishnet stockings with ankle boots - Rock this classic look fiercely.
  • Do wear pattern stockings with ankle boots - Kick your outfit up a notch by mixing pattern tights with boots.
  • Do wear boots and hosiery during cold weather - stay warm by wearing thick tights underneath your dress or skirt.


  • Don't wear ankle boots and hosiery of two different colors - Let's be honest, that's a lot going on!
  • Don't wear boots and stockings to formal occasions (unless you're going to a cowboy-themed wedding or some other exception); we recommend keeping boots at home for cocktail parties, weddings, horse racing events, and funerals.
  • Don't wear over-the-knee socks with ankle boots and a skirt. Over-the-knee-socks tend to emphasize on the exposed part of your thigh that sits between your skirt (or dress) and the top of your socks which can make your legs look short. Instead, wear thigh highs that reach the top of your thighs so that your legs will look even more fabulous!

To illustrate our recommendations, here are a few looks.

Booties and stockings
Fishnets and combat boots
Monochromatic fashion

At VienneMilano, we always believe that legs are a canvas for color and texture, and hosiery allows you to express your creativity. Ankle boots and stockings are a fabulous complement. How do you wear your boots with stockings? Leave us a comment below.

February 14, 2020

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