Wondering How To Wear A Sweater Dress With Ankle Boots? Here’s 7 Outfit Ideas For Inspiration!

Sweater dresses are one of my favorite fall fashion items year after year. They’re so easy to throw on with sneakers, boots, booties, or heels no matter what the occasion. One of my favorite ways to style them during the fall and winter is with ankle boots because it’s so easy to dress up or down. A sweater dress with ankle boots is chic, stylish, sophisticated, and effortless! If you have questions about styling a sweater dress with ankle boots, we’ve rounded up seven outfits below for some fall fashion inspiration. You might even be able to recreate these looks with pieces you already have in your closet…

By the way, if you have any questions about wearing boots with jeans make sure you check out this post next that’s full of tons of helpful information!

How To Wear A Sweater Dress With Ankle Boots

How To Wear A Sweater Dress With Ankle Boots

Sweater Dress and Boots Outfit #1

In this first look, I’m wearing a chic little black mini dress by Isabel Marant Etoile. It looks almost brown in the photo but it’s actually a really cool faded black. I love the dramatic puff shoulders and super flattering ruching around the tummy. The length is also really flattering for me, I’m 5’4” for reference. This dress isn’t called a sweater dress online but it’s a heavier-weight jersey material that’s still pretty warm. I love that this dress has a casual but modern feel.

I styled it with some Isabel Marant boots I bought a few years ago and still love. They have a western-inspired look, cool silver toe detail, and a roomier fit around the ankle and up to the calf. The dress and the boots both run TTS. You could easily recreate this look with a black sweater dress and black booties you might already have in your closet!

I talk more about these booties and ALL of my favorite boots & booties in this post if you’re looking to add some new shoes to your wardrobe.

Sweater Dress and Boots Outfit

Sweater Dress and Boots Outfit #2

This look is a bit dressier than the last one and is something I’d wear on date night or to the office (with a blazer). I have on a black Steve Madden sweater dress that’s so good…and SO affordable (only $99!). The material is thick enough to hide lumps and bumps but not too thick. So if you run hot or are dealing with hot flashes, this dress still works. I love the one-shoulder neckline that’s very flattering on most body shapes. It has a roomier fit in the waist, which will help hide any tummy concerns you may have. But the bottom half is fitted and flattering. I also love the length!

I styled the dress with my go-to Stuart Weitzman sock booties that I’ve owned for YEARS and wear with pretty much everything. Because the ankle is fitted to the leg, you can wear these booties with any jeans styles, dresses, skirts, pants, etc. Whether you love mini sweater dresses, midi sweater dresses, or maxi sweater dresses…adding a classic pair of sock booties is so easy and stylish.

For more info on the best jean styles of the year, make sure you check out this post next!

Sweater Dress and Boots Outfit Idea

Sweater Dress and Boots Outfit #3

You may remember this look from this post where I took this classic little black dress by Me+Em and transitioned it to fall with some style tweaks. Of course, one of those tips was adding ankle booties! The Me+Em dress I’m wearing isn’t technically a sweater dress, but it is a thicker material, so you can definitely wear this during the fall. I have on a pair of black patent leather ankle boots with the dress and I love the way it elevates the look. You could easily recreate this look with normal black leather boots, but the patent leather is such a cool touch! I added some polka dot tights, a belt, and a military-inspired jacket to complete the look but you can make this your own with a denim jacket, blazer, cargo jacket, or whatever you have in your closet!

open edit cardigan dress

Sweater Dress and Boots Outfit #4

If you’re looking for a sweater dress that’s super affordable, can be worn multiple ways, and is the perfect mix of casual and dressy…this is a great choice! This black cardigan sweater dress by Open Edit can be worn as a longline cardigan OR as a dress. I’m wearing it buttoned up as a dress with a pair of black leather Schutz booties. These booties are such a classic pair of ankle boots that every woman should have in her closet. I love the stiletto heel that really dresses up any look you pair them with. Styling the black sweater dress with black ankle boots keeps the line long and makes me look much taller and leaner.

See how I styled this dress as a cardigan with jeans in this post too!

sweater dress outfit for fall

Sweater Dress and Boots Outfit #5

This is an older look, but this is one of my favorite sweater dresses from a few years ago so I had to share. It’s one of those cozy sweater dresses that still looks elevated and sophisticated but is SO comfy. Unfortunately, it’s sold out, but I linked some similar options below. Another reason I wanted to share this look is because I have on the dress with combat boots! I love the edginess that a pair of combat boots brings to an outfit. All of the boots I’ve shown in the last few looks have been a little dressier…but don’t be afraid to wear flat or more casual booties with your sweater dresses too!

How To Wear A Sweater Dress With Ankle Boots

Sweater Dress and Boots Outfit #6

Next up is a sexier sweater dress option! This strappy fitted ASTR the Label knit dress is sold out, but we linked some similar options below. I love the fitted silhouette and strappy details but I know it’s not for everyone. This is a look you pull out on date night, for sure! I’ve only featured black ankle boots so for this look I wanted to show you brown ankle boots instead. I love the black and brown color combination and it’s SO much easier to wear than most women think!

If you’re looking for more brown statement boots, make sure you check out this post next.

sandro pleated trench coat

Sweater Dress and Boots Outfit #7

For the last look, I’m sharing a way to lighten up your fall/winter wardrobe with some beautiful ivory tones. This ivory sweater dress is so flattering because it’s a wrap dress. The exact dress is sold out but we linked some similar options below. I styled it with my go-to trench coat and some neutral-colored ankle boots to elongate my body. Another way I would love to style this dress is with a pair of ivory knee-high boots to dial up the sexy. But the lug-sole booties make it a bit more casual.

Do you have any questions about wearing sweater dresses with boots? Please let us know in the comments below!

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2 thoughts on “Wondering How To Wear A Sweater Dress With Ankle Boots? Here’s 7 Outfit Ideas For Inspiration!

  1. Erin – I especially love the brown suede booties with black sweater dresses! I’d love to see some focus on tights/leg covering. I live in Chicago and it’s cold AF for 6 months of the year. Help a girl out?

    1. The tights/leggings situation can be difficult…especially if you live in such a cold city like Chicago! We did a post on tights and leggings here: in case you want to check that out. Erin talks about her favorite brands and answers some frequently asked questions. If you want specific recommendations, let us know and we’d be happy to help! Thanks for reading, Trish! ~Team Busbee

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