How to Style Boots with Dresses (+ what styles look best together)

Whether you’re choosing ankle boots for style, Chelsea boots for practicality, or tall boots for warmth, this post will help you find the perfect dress to pair with each.

While you know dresses and boots go together, it’s not always obvious what pairs best. In today’s post, I cover a few common styles of boots and booties and what dresses I wear most often with them. I hope the ideas below give you some inspiration when it comes to your own closet. I’ll also share the one pair I recommend buying if you’re ready to invest in a pair of boots to wear with dresses.

How to Style Dresses with Boots

So which comes first, the dress or the boots? I tend to pick the dress out first and then start scanning my closet for shoes I want to pair it with. While I rarely plan an outfit around specific shoes, I often try on multiple pairs of shoes with the same outfit before deciding which to wear. BTW – see my 5 favorite dresses for cold weather linked in this post if you need help on the dresses front.

However, for the sake of this post (since I don’t know what your dresses look like), I’m going to break these sections down by styles of boots. That way you can scroll through the options, identify if you already own a style that I’ve outlined, and see if it might work with your dress based on my commentary.

Let’s jump in!

Chelsea Boots – casual dresses

Chelsea boots are by far the hardest shoes in my closet to style. I just don’t reach for them often. But the great thing about them is that they’re practical. They’re typically weatherproof or weather-resistant, and they’re perfect for lots of walking in colder climates. They aren’t dressy or formal, so you can nix wearing these with any dress in that category.

Chelsea boots look great with casual sweater dresses, denim dresses and skirts, and casual shirt dresses. You want to look for a dress with a little bulk (either with layers or fabric) to help balance the chunky boot.

I always wear boot socks when I wear Chelsea boots and let them show just a tad above the boot. See below.

The Chelsea boots I own are the Miah Water Resistant Chelsea Lug Boot from Nordstrom. They’re priced really well (under $100) and fit right out of the box.

Dresses to wear with Chelsea Boots:

• Sweater dresses
• Denim dresses and skirts
• Shirt dresses (add a jacket to help balance the chunkiness of the shoe)

Knee-High Boots – polished dresses

The easiest boots to style with dresses tend to be knee-high boots. While they’re great with skinny jeans, tall boots are made to be worn with dresses. Of course it depends on the actual specifics of your boots, but tall boots tend to lean dressy, and they look great when you’re wearing a dress in the winter and fall and want to feel polished.

I love styling my tall boots with polished sweater dresses, maxi dresses (the dress covers the entire boot), midi dresses (the hem will cover just the top of the boots), shift dresses, and midi and maxi skirts. It’s rare that I find a dress where tall boots don’t work!

In the cold winter, I like to wear tights with my tall boots and dresses – especially mini dresses.

I have a few different pairs of tall boots, but the most versatile pair in my closet is the Rickey Boot by Larroude (they’re pricey, but SO worth it since they’re high quality and a classic style). The heel height is perfect for everyday wear, the style is timeless, and they’re comfortable. The boots below are a bit dressier (that kitten heel makes them less casual), but they’re still a great option. They’re the Annika Faux Suede Pointed Toe Boot by Dolce Vita.

Dresses to wear with knee-high boots:

• Polished sweater dresses
• Midi dresses
• Maxi dresses (boots tucked under the dress)
• Shift dresses
• Midi and Maxi skirts

Short Booties – casual and polished dresses

Short booties are the most versatile boots in my closet. Almost every casual and polished dress works well with them, although they tend to lean more casual than dressy (in most cases). Mini, midi, and maxi dresses all look great with booties, and so do shirt dresses, shift dresses, denim dresses and skirts, sweater dresses, you name it. I’d be hard-pressed to find a dress that doesn’t work well with ankle booties.

If I were to recommend one pair of boots to keep in your closet, it would be a cute pair of heeled ankle boots. These Yanara Pointed Toe Booties by Marc Fisher LTD are a great price point and will work with most dresses in a traditional closet. The dark brown boots I’m wearing in the photos below are also amazing, but a bit of a splurge. They’re by the brand Margaux, and they’re called the Downtown Boot.

Dresses to wear with ankle booties:

• Mini dresses
• Midi dresses
• Maxi dresses
• Shirt dresses
• Shift dresses
• Sweater dresses
• Mini, maxi, and midi skirts

What are the best boots to wear with dresses?

Style is always a personal choice, but in my opinion, ankle boots are a foolproof option when it comes to styling dresses. They work well with a casual sweater and shirt dresses, dressy date night dresses (including tight-fitting bodycon dresses), and skirts of all lengths, and they also work well in an office setting. I have a blog post dedicated to how to style ankle boots with jeans as well, so you’ll definitely get more use of your booties beyond styling with dresses.

If you buy just one pair of boots, I recommend the Yanara Pointed Toe Booties by Marc Fisher LTD. They come in a handful of colors and materials, the heel height is super flattering, and the pointed toe is right on trend.

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