How To Wear A Sweater Dress With Ankle Boots: Fall/Winter Fashion

As we’re moving swiftly through the colder months, the need to find a balance between warm comfort and stylishness in our outfits increases. Sweater dresses are a must-have in every girl’s closet because they’re warm but also cozy and stylish. 

The best part is that they come in different designs, styles, and lengths to suit every need. You can probably create a different day-to-day look with just your sweater dress, footwear, and accessories.

One of my favorite ways to style a sweater dress is with ankle boots. I love them because they’re so versatile. I can easily dress my outfits up (or down) with the type of ankle boots I choose. In this article, I will show you how to attain some of my top looks.

Why Ankle Boots?

Since there are so many types of boots, I sometimes get the question, “why ankle boots?” My reply is always, “why not?”

They are stylish, versatile, chic, and very durable shoes. You can wear your ankle boots with almost any design of sweater dress and rock the look. 

Ankle boots can be open-toe, closed, flat, or heeled. They are usually crafted with:

  • Smooth leather
  • Patent leather
  • Faux leather
  • Soft suede
  • Animal print
  • Snake print
  • Pony hair

Some popular ankle boot styles include platform boots, Chelsea boots, square-toe boots, and combat boots. Although pointed-toe boots have always been the rave, you can get away with wearing square-toe-shaped ankle boots with the right clothes. 

If I’m going for a more casual but chic look, I like to pair a simple sweater dress with a block-heeled, earth-tone suede ankle boot. For something more sophisticated and fancy, a sweater dress paired with black leather pants (optional), and patent leather stiletto ankle boots with pointed toes does the trick for me. 

You can also make a bold statement by pairing your sweater dress with animal-print ankle boots. 

Ankle Boots or Booties

Pair of Stylish Ankle Boots on Orange Background

Sometimes, people mix these up because they look ridiculously alike. However, there’s a slight difference between ankle boots and booties.

As a rule of thumb, ankle boots stop a few inches higher than your ankles. However, booties tend to stop exactly on your ankle. 

For aesthetics, booties do a decent enough job of adding that extra flair to your sweater dresses. However, they provide very little protection in winter when compared to ankle boots.

How to Wear a Sweater Dress With Ankle Boots

If you’re wondering how to wear a sweater dress with ankle boots, choose a sweater dress based on your body type. Ideally, pairing your sweater dress with ankle boots is better when there’s a bit of skin showing between the top of your boots and the hem of your dress. 

To prevent your clothes from swallowing you up, smaller women should opt for dresses that end just a little above the knees (or exactly on the knees). You can also add some opaque dark tights to give an illusion of length.

There are tons of sweater dress styles ranging from belted, A-line, midi, mini, cable knit, fit and flare, and more. Here are some easy ways to style them:

Maxi Sweater Dress + Ankle Boots Combo

The maxi sweater dress and flat ankle boots combo are great for tall girls with long legs. There’s enough gap between the top of your ankle and the hem of your dress to not allow the style to drown you out. 

You can take the style up a notch by wearing a wide maxi sweater dress with a slit on the side or front for your legs to peek through.

Sweater Dress + Ankle Boots Boots + Leggings Combo

Wearing a pair of leggings with your ankle boots gives it a more seamless look, especially if the colors match. Matching black suede ankle boots with matte black leggings is a fashion hack that will always steal the show. 

However, always make sure your leggings are tight and fitted everywhere. Any loose area on the body will ruin the seamless look you’re going for and make the whole thing weird. Also, remember to buy leggings that are long enough to fit inside your ankle boots and not pop out when you move.

Mini/Midi Sweater Dress + Ankle Boots Combo

As I’ve said before, you can never go wrong with a mini or mid-length sweater dress and ankle boots combo. A pair of opaque leggings that are the same color as your boots or dress can give the illusion of length. If it’s not too cold, you can swap the leggings for a pair of socks that are just 1-2 inches higher than your ankle boots.

Sweater Dress + Combat Boots Combo

Combat ankle boots give a more robust pairing with sweater dresses because of their size. You can add a touch of femininity by pairing it with a thin-knit, soft sweater dress, or a loose one with a belt around the waist.

You can either wear a long sweater dress with a slit or a short one that ends above your knees to really show off the combat boots when you walk or sit. To glam the look up, accessorize with a wool coat or leather purse.

Sweater Dress + Chelsea Boots Combo

Chelsea boots are a special kind of ankle boots that come in different colors, shapes, and heel heights. You can never go wrong pairing them with a sweater dress. However, they’re best suited for a more casual look.

Pair your Chelsea boots with a mid-length sweater dress – especially a thinly knit one that fits snugly to your body curves. For extra flair, you can look for a sweater dress with a side slit. This type of sweater dress evens out the tough, almost masculine appearance of the Chelsea boots. 

Sweater Dresses + Sock Ankle Boots Combo

Sock ankle boots are a good idea when you want an effortlessly chic look. They have a sleek design and fit snugly around the ankles. They’re perfect with soft, thinly-knit midi sweater dresses.

To make your clothes dressier and more elegant, you can complete your look with a chain belt around the waist and a metallic clutch. 

Sweater Dresses + Western Ankle Boots Combo

Pair your short sweater dresses with Western-style ankle boots to really accentuate the look. You can also not go wrong by wearing long sweater dresses with a slit to show off the boots. 

With Western ankle boots, you don’t have to wear tights or leggings underneath. It’s perfect for fall months when the weather is not too cold outside. You can finish your look by adding a pair of dangling earrings, a hat, handbags, and a belt.

Other Tips on Wearing a Sweater Dress With Ankle Boots

Young woman wear sweater dress with ankle boots

1. Accessorize with a belt 

Adding a belt to the waist of your sweater dress upgrades the look, especially when worn with ankle boots. The belt helps to both accentuate your waistline and add an extra flair to your clothing.

If you need more coverage because of the cold weather, wear a pair of black tights or leggings under your sweater dress outfit and finish the look with a pair of black ankle boots.

2. Go bold with patterned-knit sweater dresses

When you get tired of wearing the same old plain designs, you can make a bold fashion statement by pairing a patterned sweater dress with boots.

The pattern doesn’t matter. Be it a checkerboard, ribbed, cable knit, or chunky knit design, it will add more visual intensity and pizzazz to your look.

3. Try the good old monochromatic style

When in doubt, keep it simple by going monochrome. Although understated, you can never go wrong with this style. It’s also easily accessible and almost anyone can put together this elegant look.

Grab a monochrome sweater dress and keep your ankle boots neutral. You can dress the look up by adding a monochrome coat and neutral bag. 

4. Dress your look up with a blazer

Wearing a blazer over your sweater dress and ankle boots combo can give you an extra layer of warmth in colder months. Layer your sweater dress with a blazer with a contrasting color to make your outfit stand out. Finally, finish your look with your favorite scarf and you’re ready to go.


Ankle boots are one of the most stylish options you can pair with sweater dresses. You can attain a wide range of looks with them and even accessorize to dress your look up (or down, as the case may be.)

You’ll be amazed by how much difference adding a pair of bold, stylish, ankle boots will make. If you’re not quite sure of how to wear a sweater dress with ankle boots, then this article is a good place to begin.

I’ve explored many options for people with different tastes and body types. So don’t be afraid to explore a new way to make your outfits more stylish this winter, and start pairing your sweater dresses with ankle boots!

For more fashion tips and styles, read my collection of articles

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