Chelsea boots are one of the biggest shoe trends. If you’re trying to figure out how to wear them with dresses, here are 4 easy looks. 

Chelsea Boots With Dresses

Chances are you’ve probably bought a pair of Chelsea boots in the past few years. While these boots are so easy to wear with jeans and leggings, pairing boots with dresses can be a little trickier.

I’ve shared about THESE CHELSEA BOOTS for the last year (I bought them last January) and they have become a staple in my closet. They’re currently sold out, but they have restocked several times and then quickly sell out again.

So if you see them in your size, GRAB A PAIR! They’re true to size, a little stiff at first, but then soften beautifully and become insanely comfortable. Hundreds of you have purchased them and love them as much as I do.

Here are 4 looks for you to copy and style tips to make boots and dresses outfits work.

1. Try your boots with a shorter dress and long coat

A knee length dress works great with a pair of Chelsea boots (as long as they’re slim in the ankle)! The big gap of bare leg allows the leg to look elongated and not stumpy.

If you need more warmth, you can wear a pair of tights. And of course I put a long, slim-cut coat over the top!

SIMILAR BROWN DRESS HERE, HERE and HERE | SIMILAR WOOL COAT | BLACK CHELSEA BOOTS | MADEWELL BEADED EARRINGS

2. Try your Chelsea boots with a sweater dress and socks

These boots look great with a shorter sweater dress or a longer sweater dress. The slit helps elongate the leg, but it’s not necessary (case in point..check out THIS POST).

But with a long dress like this, a peek of sock between the leg and the boot (especially if you have lighter skin like me), helps soften the look so the boot isn’t so harsh of a line across your ankle.

LOFT SWEATER DRESS | AMAZON BLACK BELT | AMAZON TALL SOCKS | BLACK CHELSEA BOOTS

3. Chelsea boots work great with a shirt dress

This is not the best example of a shirt dress, but it’s all I have right now so we’re going with it. Chelsea boots look great with more structured dresses, especially if they’re belted and you have a defined waist.

Again, I added a tall sock to soften the look of the boot against the leg.

WHBM ZIP UP SHIRT DRESS | AMAZON TALL SOCKS | CHELSEA BOOTS 

4. Chelsea boots even work with more feminine dresses

These boots even work with more feminine dresses! No, these shoes wouldn’t be my first choice with this dress (I wore this last week with sheer tights and heels as seen HERE), but they’re slim and sleek enough that they do work!

Since they’re a little bit chunky with their lug sole, I’d wear a coat with this look to balance the heaviness of the shoe just a bit.

Also to help create more of a sleek look, I added black tights.

WHITE HOUSE BLACK MARKET FLORAL DRESS | SIMILAR BLACK TURTLENECK   | BLACK TIGHTS | BLACK CHELSEA BOOTS

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