How to Wear a Short Dress With Boots

Readers have often asked if they can wear boots with a short dress and the answer is yes – absolutely! Boots are some of the best shoes to wear with dresses for fall, winter and cooler summer days.

When styling short dresses with boots, proportions are key. This means balancing top and bottom parts of the short dress outfit.

I’ll specify which type of short dress and boots to choose, including how to complete the outfit with the right purse, accessories & outerwear.

Reach for buttery black leather, or patent leather ankle boots with a pointed toe and stiletto heel to wear with a fancy short dress.

Short Dresses with Ankle Boots


Both frilly, flowy and tiered short dresses look great with Western boots. However, they can look great with tight short dresses and an oversized cardigan, or jacket too.

Short Dress with Cowboy Boots


I prefer a short dress with knee high boots without hose or leggings – but they can look just as good with them!

Short Dress with Knee High Boots


Whether you choose a super short style or something closer to your knees, combat boots will help to ground the short dress outfit.

Short Dress with Combat Boots


For a formal occasion, sock boots can impress in a high shine or velvet material. A high stiletto heel and pointed toe always makes things fancier.

Short Dress with Sock Boots


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