Taller boots are trending, and can pack quite the visual punch. They are insulating too. If you have a pair that you like but aren’t wearing, dust them off and wear them with dresses. 

Here are ways to wear dresses with tall boots as the weather cools.

1. Summer Dress with Taller Boots

This is dead easy. Pair a summery dress with a pair of tall boots. Add a bag that works with the palette of the outfit, and Bob’s your uncle. Here, a shorter dress with a boho vibe is combined with toffee cowboy boots. A tan bag is a tonal match to the boots. A casual necklace on black cord completes the look and fills the gap created by the low neckline.

Summer Dress with Taller Boots

Here are examples of adding taller boots to longer dresses that you typically might wear in the Spring and Summer. The boots are not cowboy boots. A simple way to move dresses into transitional weather, as long as you have the boots.

2. Dresses with Stompy Black Boots

Here’s a version with an on-trend ‘90s flavour. Dresses can be solid or patterned and any length. They are usually made of soft fabric and have black in the patterns to match the boots. Stompy boots are generally black, relatively flat, casual, and chunky. Boot heights tend to be mid-calf, but shorter and taller boots work well too. This version adds a black bag to match the boots, and a canary yellow coat to complement the ochre in the pattern.

Dresses with Stompy Black Boots

Here are more ways to wear dresses with stompy boots. Black bags match the black boots. Sometimes they match a black topper. Where there is no black in the outfit, black boots match the black hair of the model.

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Puff-sleeve Midi Dress
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Pleated Shirt Dress
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Belted Shirt Dress
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Pleated Shirt Dress
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3. Transitional Dresses with Taller Boots

This is an example of a warmer dress that you can wear with tall boots. It’s typically thicker, longer and has sleeves.The navy dress here is combined with brown boots and a belt to match, which is nice with the model’s brown hair. A cream coat adds a crisp and pretty touch. I vote a bag that matches the palette, or throw in an unexpected pastel or bright.

Transitional Dresses with Taller Boots

Here are a few more examples of warmer dresses with tall boots. The dresses are midi and midaxi length, and the boots are quite dressy. Bags do not need to match the boots. You might be warm enough wearing this look in Winter, especially indoors.

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MISA Charlotte Dress
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4. Short Dresses with Taller Boots

Last, if you prefer dresses with shorter hemlines, here are ways to wear those. Hems range from mid-thigh to just above the knee. These silhouettes are waist-defining, but feel free to surrender the waist. Boxy and voluminous cuts look great with tall boots.

Now that I have a pair of gorgeously tailored knee-high boots, you can bet your bottom dollar I’ll be wearing them with some of my midi and midaxi dresses. I love how I can extend the wear of some of dresses in this way. Can’t wait!