How To Style a Sweater Dress with Boots: 10+ Looks I Love

Wondering how to style a sweater dress with boots? I’ll show you all the ways you can wear different styles of sweater dresses with different styles of boots for the fall and winter seasons!

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@style.your.occasion

How To Style A Sweater Dress with Boots 

I always have a few sweater dresses on rotation come fall and winter. But even more important than what sweater dress you choose to wear are the shoes you pair with it. 

While sneakers or loafers seem like an obvious choice, pairing your sweater dress with on-trend boots creates the perfect chic yet cozy vibe that will keep you warm and stylish on crisp autumn days. There are dozens of ways to style these two pieces together and some key things you want to avoid. But don’t worry: styling a sweater dress with boots is much easier than you may think.

My style guide walks you through exactly how to do it. Take a cue from the outfit inspo below and get ready to fall in love—if you weren’t a sweater dress and boots person before, you will be now. 

Chic Sweater Dress with Boots Outfits 

What are the best boots to wear with sweater dresses? Below are the best options to style all fall and winter long.

Ankle Boots

Ribbed knit dress + ankle booties.

Woman wearing a grey sweater dress with black booties and a black purse.
@rosalieedith

When in doubt, pair your sweater dress with ankle boots. They’re the ideal height for a maxi dress and are comfy enough to wear walking around the office or city. 

A ribbed knit sweater dress looks chic and refined with pointed-toe ankle boots and coordinating accessories. I love black leather boots like the one pictured here, but you can also swap them with white booties to make your neutral look pop.

Blazer, midi dress + Western boots.

Woman wearing a cream sweater dress with black booties and a black blazer.
@style.your.occasion

get the look:

Switch up your styling by swapping everyday ankle booties for Western-inspired ankle boots which have been very on-trend in 2023. 

These pointed-toe booties look super stylish with a midi sweater dress in any fabric or color. A blazer takes the look to the next level for an end result that’s modern with a touch of cowgirl flair.

Maxi dress + statement boots.

Woman wearing an orange sweater dress with silver booties.
@melissavillarreal

I absolutely love that metallics have been all the rage in fashion this year, and the trend continues.

Keep fall fashion fun with a pair of statement ankle boots. This orange knit sweater dress is the perfect autumnal color, and it really pops against these metallic Western-style booties. To keep things more subtle, wear your statement boots with a black or neutral-colored maxi dress.

Trench coat, midi dress + combat boots

Woman wearing a black sweater dress with brown chelsea boots and a tan trench coat.
@style.your.occasion

get the look:

Combat boots are one of those fall shoes everyone has in their closet. Next time you’re styling a sweater dress, try your combat boots with it. These timeless boots are perfect for rainy or muddy fall days and are way more practical than heels.

I strongly believe that midi dresses pair well with combat boots—just be sure the length comes to a flattering point, like right above or slightly below the knees. A lightweight knit sweater dress lets you stay cozy but is cool enough to layer with outerwear, like this gorgeous vanilla-hued trench coat.

Can a sweater dress be dressy?

Yes! Sweater dresses are a versatile wardrobe essential that can be dressed up or down depending on the styling. Most sweater dresses are inherently dressy enough for work, a nice dinner, or an event, especially during the fall and winter.

Make your outfit even more classy by pairing it with a blazer or trench coat and a chic pair of knee-high leather boots or heels. Add some sparkle with high-quality jewelry and a stylish bag, and voila! You look smart and sophisticated while staying cozy.

Over-the-Knee Boots

Woman wearing a white sweater dress with brown over the knee boots, a tan coat and a tan hat.
@natalie.yerger

Styling a shorter sweater dress? I recommend playing with proportions by adding an over-the-knee or thigh-high boot. I love how this creamy mini dress pairs with caramel suede over-the-knee boots, leaving just a sliver of skin showing.

Keep things tonal with a matching suede bag, wide-brimmed hat, and cozy wool jacket for the perfect layered autumn look. And because over-the-knee boots are such a statement, choosing the right heel height is important. Flat heels provide a more casual look that’s ideal for every day, while higher heels look better for a night out or a special event. 

Knee-High Boots

Midi dress + knee-high boots.

Woman wearing a cream sweater dress with tall black boots
@style.your.occasion

get the look:

Knee-high boots and a midi dress are always a chic combo—but I recommend that the dress hem covers the top of the boot for a seamless silhouette, like in the outfit on our Editor-in-chief above. 

A general rule of thumb is to leave at least a few inches between the dress hem and the top of the boots. Alternatively, you can completely hide the tops of your boots beneath the sweater dress (as seen above) which gives a modern vibe we are seeing everywhere this season. 

Elevate the look with a timeless shoulder bag and sunglasses, or add a belt to define your waist.

Long sweater dress + pointed-toe boots.

Woman wearing a black sweater dress with chunky black boots.
@nellycom

I love how a long sweater dress looks draped over knee-high boots. A monochromatic moment instantly dresses up your sweater dress and elongates your figure. Match your accessories to the color scheme for an effortlessly cool and luxe look. 

A fitted sweater dress is sexy and sophisticated, but you can try this look with chunky cable knit or ribbed textures, too. 

Wool coat, mini dress + slouchy boots.

Woman wearing a black sweater dress with tall black boots and a brown coat.
@style.your.occasion

get the look:

Knee-high boots are the perfect partner for mini dresses!

I love that these black leather boots complement the form-fitting sweater dress for a look that is *chef’s kiss*. To make the outfit more cold weather appropriate, throw on a long wool coat or trench, and add stockings for extra warmth.

Finish with dainty jewelry and a practical shoulder bag.

Mini dress + croc-effect boots.

Woman wearing a black sweater dress with tall black boots and a black purse.
@thefashionbugblog

In my opinion, this outfit proves that you can totally dress up a sweater dress with boots. To do so, pair a mini sweater dress with sleek knee-high boots (this shoe style leans more formal). These elegant croc-effect boots add texture and interest, but any heeled tall boot will do the trick.

To finish off this dressed-up look, add sheer black tights, cat-eyed sunglasses, and a black leather tote that fits all your essentials.

Chelsea Boots

Denim jacket, fitted dress + Chelsea boots.

Woman wearing a black sweater dress with black Chelsea boots and a denim jacket.
@style.your.occasion

get the look:

Pair your Chelsea boots with a midi-length sweater dress for a laidback fall look like Christal, our Editor-in-chief did above. 

In this outfit inspo, the slim-fitting sweater dress and boots perfectly balance the oversized denim jacket. Adding a denim jacket brings a bit of color and interest to your outfit while staying fall appropriate.

Finally, finish the look with your go-to shoulder bag or backpack to keep your hands free.

Sweater dress, leather jacket + lug boots.

Woman wearing a cream sweater dress with black Chelsea boots and a black leather jacket.
@style.your.occasion

get the look:

Lastly, this sleek and simple outfit will keep you cozy on chilly fall days.

To start, grab a long-sleeved cream sweater dress and wear it underneath a black leather jacket for a cool (yet warm) layer. Finish the look with chunky Chelsea boots for a versatile look you can wear to date night or at brunch with your besties.

Wherever you’re going, this outfit combo is one fashion lovers swear by!

How do you wear a sweater dress and boots? 

A sweater dress and boots are a matchmade in fashion heaven—you can’t go wrong with this pairing. Here’s how to wear boots with a sweater dress in a stylish way:

Ankle boots: This easy, versatile shoe can be worn with any length of sweater dress, though it looks especially great with a midi or maxi dress. Flat ankle boots are a casual option that’s comfortable to walk in. Dress your look up with heeled ankle booties.

– Knee-high boots: For a look that screams high fashion, reach for knee-high boots. These tall boots will keep you warm and stylish underneath a midi or maxi-length sweater dress. They also look super flattering paired with a mini sweater dress. 

– Over-the-knee boots: This iconic fall shoe option looks best when worn with a mini-length sweater dress. The key here is to keep the top part of your thigh exposed to elongate your figure. If it’s too cold to show off those legs, layer with tights or opt for a longer sweater dress.

– Chelsea boots: Chelsea boots are a sleek and sophisticated option when it comes to styling sweater dresses. They look great with a midi-length dress and are comfortable to wear all day long. For a chunkier option, go for a lug boot instead.

– Cowboy boots: If you want to spice up your sweater dress outfit, pair it with cowboy or Western-style boots. The styling for this on-trend shoe combination works similarly to if you were wearing ankle boots or tall boots. Western-style ankle booties are the most versatile and add Western flair to a midi or maxi-length sweater dress. Reach for knee-high cowboy boots when wearing a mini or midi sweater dress.

– Combat boots: Add some edge to your sweater dress outfit with combat boots. This quintessential fall shoe looks amazing paired with any length of sweater dress. For shorter dresses, rock them with black tights and an oversized jacket for the ultimate cool girl vibe.

Final Notes

As you can see, there are endless ways to style your sweater dress with boots. Whether you opt for ankle booties, combats, or thigh-high boots, this pairing is a surefire way to look stylish all autumn and winter!

 

More Style Inspiration You’ll Love:

How To Wear A Sweater Over Dress: Chic Outfits + Styling Tips!

How to Wear a Dress in Winter: Tips & Ideas for Cold Weather

The Best Shoes To Wear With Sweater Dresses + Chic Outfit Ideas

What Shoes To Wear With Black Dress + Stunning Looks To Steal

The Best Shoes To Wear With A Long Dress for Any Occasion

About

Hi! I'm Christal - Editor-in-chief, published author, and minimalist fashion enthusiast! Welcome to Style Your Occasion, your styling inspiration go-to for every occasion, event, party, and trip! Click below to meet the rest of the Style Your Occasion team.

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