Sweater Dress With Boots: How to Wear The Fabulous Fall Look


For all those who are already dismayed at the idea of packing away their summer outfits in lieu of colder days, fear not. Fall is the perfect time for pulling out all those cozy sweater dresses and pairing them with your favorite boots. A sweater weather staple, you can choose from a snug-fitting sweater dress with knee-high boots for that sexy femme look or opt for the comfy oversized sweater dress with chunky boots to embrace that casual chic look with a razor-sharp edge.

No matter which long-sleeve outfit you're after, when paired with some cute booties and colorful tights, you'll be able to stay both comfy and fashionable in the cold weather this fall season.

This simple two-step look ticks all the boxes, carrying us from drizzly walks in the park to wine nights with friends. Here’s how to make the most of this swoon-worthy style and stay soft, cozy, and in style until spring…


How to Wear a Sweater Dress With Boots

One of the unwritten rules of wearing a sweaterdress with boots is keeping a little contrast in color and texture between the boots, tights, and sweater. Wearing this look with at least a slip of space between the hem of the dress and the top of the boots gives this cute outfit a sexy twist.

While there are no hard or fast rules on which boots should steer clear of which dress, there are a couple of tips that could help ease the look along.

But remember, in fashion rules are made to be broken! It’s all about experimenting and finding a style that works for you. The aim is to try and avoid a rumpled look by having the dress sit heavy over the boots. Instead, try and give the look room to breathe. After all, it’s absolutely OK to wear a dress with boots and keep it looking light – even in the midst of winter.


Different Types of Sweater Dresses

The first thing to know when constructing the perfect sweater dress and boot combo is that there are several different types of sweater dresses that you can work with. Some you can wear all winter long while others, like those with a short sleeve or an even shorter hem, you will want to wear only in the months just outside of winter.

As a general rule of thumb, let your boots balance out your sweater.

So you've got a big comfy sweater? Slip into some knee-high leather boots for a sexy yet comfy style.

Working with a hip-hugging turtleneck dress? Pair with some sleek suede booties and black leggings.

The possibilities are endless and no matter what you wear this winter, you'll be a total fashion icon.


Turtleneck Sweater Dresses

Wrap up in wonder this fall as you snuggle down in the warming turtleneck sweater dress. Remarkably, the turtleneck is a style that has stood the test of time. It is the perfect fashion trend to wear as we approach winter and can be worn both at work and at after-work-shenanigans.

When looking for a cute turtleneck dress, shop for a form-fitting style for a sexy sleek look. If you like the cozy look, then you can opt for a thick turtleneck dress to pair with knee boots.

Combining the sheer comfort of a turtleneck with the slick sweater dress style, you can stay shiver free and fabulous without the need to don a scarf even on the chilliest on days.


Maxi Sweater Dresses

Magical maxi dresses don’t have to be saved for the whimsical summer wedding scene. You can keep your love of the long flowing dress style this autumn and winter... and right through til spring. Simply swap out that thin cotton material for a woolen maxi sweater dress or a lush long knit to stay soft and warm from tip to toe. Pair with your favorite booties and you've got an easy-breezy fashion statement.


Knit Dresses

Heavier than your usual lightweight sweater dress, the knit dress is one of the most popular styles of sweater dress to add to your closet when it comes to cold-weather looks. The knit dress usually comes in either a tight figure-hugging weave, a chunky cable knit, or a sublimely soft wool mix to help keep you warm during these upcoming cold months.

The best part?

This style is great for lounging around at home too. Just kick off your suede boots and slip on some comfy socks for an outfit that's perfect for cozying up with a book and hot cocoa.


Different Types of Boots To Pair With Sweater Dresses

Let's be honest, the real show-stopper in this outfit combo is hardly the sweater dress. After all, if you wear a sweater dress by itself, you might as well be wearing a super chic nightgown. But when paired with a sexy pair of knee boots or with super chic leather booties, then your sweater dress with boots combo becomes something of a fashion statement.

These are the cutest types of boots that you can pair with your cozy outfits this fall and winter.


Knee High Boots

The sexiest style of boots to blend in with your winter or fall outfit, knee-high boots are enchantingly feminine and naturally make the legs look longer. From butter-soft leather boots to fuzzy soft suede boots, there are tons of styles out there and even more ideas for your sexy combo. If you are looking for a classier knee-high look or if you want to reduce the tall woman look slightly, then steer clear of the shiny patent style with a stiletto heel and instead choose something flat or slightly elevated.


Ankle Boots

Embracing the chic city look, snappy little ankle boots are an amazing pairing for the sweater dress that lend a flattering look to just about any height or body shape. Short booties and a dress is a super modern and vibrant style that every fashion lover has in their back pocket. And while it may leave legs exposed to the elements, you can also pair with tights (as long as not too blocky in color) to keep warm.


Combat Boots

If you want to skip out on the dainty boots and dress look, then add an edge with some chunky combat boots. Combat style shoes are way more versatile than you would think and can even be paired with more feminine print sweater dresses (along with muted tones) for a contrasting look that oozes confidence. Wearing these boots will make going out into the cold seem a whole lot less daunting.


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Popular Combos For Pairing Boots and Sweater Dresses

Okay, so you need a little guidance about the best way to be wearing this classic fashion combo? We're here to help you. We've rounded up some of the best fashion bloggers who are wearing our beloved outfit combo to show you how to wear your favorite sweater dress this season. Take a look at these outfits that we love and then shop the looks.


1. Big Turtle Neck Sweaterdress and Knee Highs

Don a cozy oversized sweaterdress with a turtle neck for maximum comfort. Pair with over-the-knee boots sporting a flat or slight heel for a super chilled yet stylish look. This outfit is the perfect choice for those days when you need room to breathe, snugly fun, and chic versatile style.

Get the look:



Photo Credit: confessions of vanity

Shop Similar styles: The Samantha Dress can pull off knee-highs and a thick cardigan


2. Curve Hugger Midi and Booties

Shapley and svelte, long knitted dresses don’t need to turn you into a frump but can instead veer towards a sexy look with jaw-dropping power. Pick a midi with a silhouette style (clinging to all the right places) and preferably in a bold color or print for added zazazoom. Pair with short snappy boots in a pale or creamy color to add balance, especially for tall women.

Get the look:



Photo Credit: Awed by Monica

Shop Similar styles: The Michelle Dress shares that curve hugging look we love in a maxi


3. Oversize Sweater with Combat Boots

Beatnik style is alive and well in this easy and slightly moody look of oversized athletic sweater with chunky boots. Choose a dress in darker wool and don’t shy away from form-fitting style. Pair with chunky combats and get ready to kick some ass. Wear with a leather jack and a warm scarf for a classic look that will last all season.

Get the look


oversized athletic sweater with chunky boots

Photo credit: @molcosier

Shop Similar styles: Mix and match with this Skylar Tie-Dye dress with chunky boots


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4. White Turtle Neck with Black Suede Knee Highs

Nothing says great style icon like turning up the dial on those classic white on black looks. Choose a white fuzzy turtle neck sweater dress (you can go loose or tight, depending on personal style preference just make sure it's short). Pair your white sweater dress with elongated black suede knee boots with a slight point and heel to truly embrace femme fatale style this winter.

Get the look: 

Photo Credit: Catherine V

Shop Similar styles: While it won’t suit high boots, this Lanai Jumpsuit is as fresh and pure as any look gets


5. Sleeveless Sweater Dress with Long Shirt and Camel Ankle Boots

Preppy and perfect for back to school season, this vibe has a touch of cute Clueless classic to it but has been modernized for our 21st century. A navy or dark wool fitted knit without sleeves shows just the right amount of patterned plaid. Give your legs some room to breathe with low camel colored anklets in white or suede or match with black boots.

Get the look



Photo credit: Cassey Cakes

Shop Similar styles: Throw some plaid over this August Romper and pair with booties for a country chic look


6. Wool Dress and High Boots with Flannie 

Super warm, layered, and with just the right amount of attitude, pairing a knit dress with high boots and a flannel or cardigan is one of those bold and beautiful looks that works wonders for those graced with a good amount of height. Be sure to alternate prints between your cardi and dress (one bold in color and pattern and one muted and block colored will work).

Get the look


casual sweater dress with knee high boots

Photo Credit: @champagnetaste_blog

Shop Similar styles: The Luna Cardigan will lend a snuggly look to any dress


7. Short Sweater Dress with Riding Boots

The short sweater dress with chunky riding boots combo is a winning look just begging to be worn. This is a casual sophisticated look especially when you choose an oversized sweater dress with a short body. Pair with dark leggings and big riding boots for an edgy street look.

Get the look


Photo credit: Miamiyu

Shop Similar styles: On warmer days you can swap out the sweater for this Bailey Romper and boots


8. Sweaterdress with Cowboy Boots

While you may think ride em high cowboy boots are only for tucking in your Levi jeans, these buttery soft tan boots actually look incredible when paired with the right kind of sweaterdress. A black wool mini or turtleneck sweaterdress with some leg brings modern country looks to the show.

Get the look


Photo credit: Eniko S, @enikoschmidt

Shop Similar styles: This Devon Dress would look divine with cowboy boots


9. Cotton Sweaterdress and Ankle Boots

Who said the sweaterdress look has to be all wool and chunky knit? For softer climates or warmer days, don a cotton sweaterdress with ankle boots and embrace that all casual appeal. The long sleeve cotton summer dress offers great comfort and laid-back class especially when in muted colors. When it gets chilly, slip on a knitted cardigan. 

Get the look


Photo credit: Normal Naya

Shop Similar styles: Embrace casual cool with the Calista Dress


10. Bold Patterned Sweaterdress with Combats

Opt for a short and flirty bold print sweaterdress and pair with combats boots to mix up that feminine and slightly masc look that radiates attitude. Multiple block color patterns or bold stripes are always a good look especially when paired with tights and chunky boots for fall days.

Get the look



Photo credit: Suzi West


Shop Similar styles: The Heidi Dress shares a bold patterned look


Which sweater dress style are you loving? Share your fave combo with us in the comments and let’s stay soft and cozy this fall.


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