Dresses With Ankle Booties: How To Achieve The Perfect Look

Ankle boots are a staple in every fashion lover’s wardrobe. They are versatile, stylish and can be worn with a variety of outfits–including dresses!

Dresses with ankle boots make for a perfect combination that showcases cute comfort and style. Today, I’ll be showing you how to style your ankle boots with different types of dresses. 

Whether you prefer mini, midi, or maxi dresses, I’ll show you how to style all types of dresses with ankle booties. I will include the best ankle boots for dresses, places to shop for them and answer some top styling questions.

So, sit back, relax, and read on to learn more about how to wear ankle boots with dresses!

Disclosure: Vain Affair is reader-supported. When you buy through affiliate links on our website, we’ll make a small commission, without impacting your price. Thank you. Learn more.

In This Post ➜

1. How to Wear Ankle Boots with Dresses + Pictures!
2. Mini Dresses With Ankle Boots
3. Midi Dresses with Ankle Boots
4. Maxi Dresses with Ankle Boots
5. Sweater Dress with Ankle Boots
6. Shirt Dress with Ankle Boots
7. Denim Dress with Ankle Boots
8. Leather Dress with Ankle Boots
9. Cocktail Dress with Ankle Boots
10. LBD (Little Black Dress) with Ankle Boots
11. Best Ankle Boots for Dresses
12. Places to Shop for Ankle Boots for All Budgets
13. Styling a Dress with Ankle Boots & Tights or Leggings
14. How to Wear Ankle Boots with Dresses over 50
15. Ankle Boots with Dress for Wedding Guest
16. Frequently Asked Questions

How to Wear Ankle Boots with Dresses + Pictures!

Ankle boots are a versatile and stylish addition to any outfit, and when paired with dresses, they can take your look to the next level. However, knowing how to style ankle boots with dresses can be a bit tricky, especially if you’re not sure what types of ankle booties go with what dress styles.

In this section, we will show you how to wear ankle boots with different types of dresses–everything from a mini to a cocktail dress! 

I will also provide picture examples of each combination so you can see how to put together the perfect look. So, let’s get started on how to wear ankle boots with dresses!

Mini Dresses With Ankle Boots 

Mini dresses are a great way to show off your legs and create a chic and flirty look. Pairing them with ankle boots can add a touch of edginess to your outfit and make it perfect for any occasion. 

When it comes to styling mini dresses with ankle booties, there are a few things to keep in mind to ensure you get the look just right.

1. Length Matters: The length of your dress is crucial when pairing it with ankle boots. The ideal length for a mini dress with ankle boots is mid-thigh or slightly above the knee. This length is the most flattering on pretty much all body types.
2. Play with Proportions: When wearing ankle boots with a mini dress, it’s important to balance the proportions. Opt for a shorter ankle boot style to elongate your legs or try a chunky heel to add some height.
3. Keep it Simple: Mini dresses are already a statement piece, so keep your ankle boots simple. Classic black leather ankle boots or suede ankle boots in neutral colors are perfect for pairing with a mini dress.

Ankle Boots That Pair Well with Mini Dresses:

• Classic Black Leather Ankle Boots
• Suede Ankle Boots in Neutral Colors
• Pointed Toe Ankle Boots
• Chunky Heel Ankle Boots

Midi Dresses with Ankle Boots

Midi dresses are a wardrobe staple that can be worn all year round, and they look great when paired with ankle booties. However, styling a midi dress with ankle boots can be tricky. 

Here are some tips to help you pull off this stylish look:

1. Choose the Right Length: The ideal length for a midi dress when wearing ankle boots is below the knee or mid-calf. This will help balance out the proportions and show off your ankle boots.
2. Opt for Fitted Styles: A fitted midi dress looks great with ankle boots because it accentuates your curves and elongates your legs. Choose a midi dress that is fitted at the waist and hips, and flares out slightly towards the bottom.
3. Mix and Match Textures: Ankle boots come in a variety of textures, such as suede, leather, and velvet. Experiment with different textures to add interest to your outfit. For example, pair a suede midi dress with leather ankle boots, or a velvet midi dress with suede ankle boots.

Ankle Boots That Pair Well with Midi Dresses:

• Chunky Heel Ankle Boots
• Pointed Toe Ankle Boots
• Peep Toe Ankle Boots
• Wedge Ankle Boots

Maxi Dresses with Ankle Boots

Maxi dresses are a summer wardrobe essential that can be dressed up or down, and they can be worn with ankle boots to create a chic and stylish look.

Here’s how to style a maxi dress with ankle boots:

1. Check the Length: When wearing ankle boots with a maxi dress, make sure the dress length ends just above or at the ankle. This will ensure that your ankle boots are visible and create a balanced silhouette.
2. Play with Proportions: To balance out the volume of a maxi dress, choose ankle boots that are slim and streamlined. Avoid chunky boots, which can overpower the flowy silhouette of a maxi dress. Instead, go for ankle boots with a pointed toe, which will elongate your legs and create a flattering look.
3. Look for a Leg Slit: Since maxi dresses are so long, a nice leg slit will help showcase your ankle booties every time you move. Plus, it’s a great way to show off your legs and stay cool in the hot weather. 😉

Ankle Boots That Pair Well with Maxi Dresses:

• Flat Ankle Boots
• Block Heel Ankle Boots
• Cowboy Ankle Boots
• Peep Toe Ankle Boots

Sweater Dress with Ankle Boots

Sweater dresses are a great option for colder weather, and ankle boots can provide the perfect finishing touch to your look.

Here are some tips for styling sweater dresses with ankle boots:

1. Pick the Right Length: By now you should be getting the idea–length matters! Sweater dresses come in a variety of lengths, from mini to maxi. When pairing them with ankle booties, it’s important to consider the length of the dress. For a more balanced look, go for a midi or knee-length sweater dress. If you prefer a shorter dress, pair it with ankle boots that have a higher shaft to avoid looking too exposed.
2. Experiment with Textures: Since both sweater dresses and ankle booties are typically made of thicker fabrics, it’s a good idea to mix up the textures to add some dimension to your outfit. Try pairing a chunky knit sweater dress with suede ankle boots or a ribbed sweater dress with leather ankle boots.
3. Play with Color: Don’t be afraid to mix and match colors when styling a sweater dress with ankle boots. Neutral ankle boots like black or brown can complement almost any sweater dress color, but don’t be afraid to experiment with bolder colors or prints.
4. Accessorize: Adding some accessories like a statement necklace, scarf or hat can elevate your sweater dress and ankle boots look to the next level.

Ankle Boots That Pair Well with Sweater Dresses:

• Combat Boots: Pairing a chunky sweater dress with combat boots creates a perfect balance of edgy and cozy.
• Chelsea Boots: Sleek and versatile, Chelsea boots can be dressed up or down and can work with almost any sweater dress.
• Over-The-Knee Boots: If you’re going for a more daring look, over-the-knee boots can add some extra warmth to your sweater dress and also elongate your legs.

Shirt Dress with Ankle Boots

Shirt dresses are versatile and perfect for any occasion, whether it’s a casual outing or a formal event.

Ankle booties with shirt dresses pair really well together. Here are some helpful tips to get you started in styling shirt dresses with ankle boots.

1. Keep it Simple: Opt for a classic ankle boots in a neutral color like black or brown to complement the simplicity of a shirt dress.
2. Accessorize: Add a belt to cinch the waist of the shirt dress and pair it with ankle boots for a stylish look.
3. Show Some Skin: If you’re wearing a shirt dress with long sleeves, roll them up to your elbows and pair the outfit with ankle boots to show some skin and create a balance. This is great for casual outfits, but don’t roll up your sleeves for more formal events!
4. Play with Textures: Pair a silk or chiffon shirt dress with suede or leather ankle boots for a chic look.
5. Length is Key: Ensure the length of the dress falls just above the knee or a few inches below to avoid an awkward length that will make your legs appear shorter. Kind in mind that you’ll want a longer length that falls art or below the knees for more formal events.

Ankle Boots That Pair Well with Shirt Dresses:

• Chelsea boots
• Heeled ankle boots
• Suede ankle boots

Denim Dress with Ankle Boots

Denim dresses are a timeless wardrobe staple that can be styled in a variety of ways. Pairing them with ankle boots can give them a fresh, modern update.

Here are some tips on how to style denim dresses with ankle booties:

1. Choose the Right Denim Wash: When choosing a denim dress to wear with ankle boots, pay attention to the wash of the denim. Lighter washes pair well with brown or tan boots, while darker washes look great with black boots.
2. Choose the Vibe: Many types of ankle boots pair well with denim dresses, including chunky boots, stiletto boots, and western-inspired boots. Pick a style that complements the vibe of your dress.
3. Layer with Tights: Depending on the weather, layering your denim dress with tights can give it an extra edge and make it more appropriate for colder temperatures. Black opaque tights are a classic option that pairs well with ankle boots.

Ankle Boots That Pair Well with Denim Dresses:

• Chunky black boots
• Pointed-toe ankle boots
• Western-inspired ankle boots
• Suede ankle boots
• White ankle boots

Leather Dress with Ankle Boots

Leather dresses are a stylish and edgy choice for any occasion, from a casual night out to a formal event. But when it comes to styling them with ankle boots, it can be tricky to strike the right balance between casual and chic.

Here are some tips to help you pull off this look with confidence.

1. Keep It Minimal: Since leather is already a bold statement, opt for simple ankle boots to balance out the look. Black leather ankle boots are a classic option, but you can also try nude or beige ankle boots for a softer touch.
2. Accessorize Wisely: Keep your accessories simple and minimal. Avoid adding too many statement pieces as they may clash with the boldness of the leather dress and ankle boots.
3. Go for a Monochromatic Look: Pairing a black leather dress with black ankle boots creates a chic and sleek monochromatic look. You can add a pop of color with your handbag or jewelry.
4. Play with textures and patterns: To add dimension to your outfit, experiment with different textures and patterns. For instance, pair a shiny patent leather dress with suede or snakeskin ankle boots. Mix and match to create fun looks!

Ankle Boots That Pair Well with Leather Dresses:

• Pointed-toe ankle boots: They add a touch of elegance and sophistication to your outfit.
• Chunky ankle boots: These boots give off an edgy and cool vibe that perfectly complements a leather dress.
• Stiletto ankle boots: If you want to elevate your outfit and make it more formal, stiletto ankle boots are a perfect choice.

Cocktail Dress with Ankle Boots

When it comes to dressing up for a cocktail party or evening event, ankle booties with dresses might not be the first thing that comes to mind. However, ankle boots can be a stylish and unexpected pairing with a cocktail dress.

Here are some tips for rocking ankle boots with your favorite cocktail dress:

1. Neutral Colors Are The Way To Go: Choose ankle boots in a neutral color such as black, brown or nude to keep the focus on your dress.
2. Choose the Right Style: Ankle boots with a sleek, pointed toe and stiletto heel can add some glam to your outfit, while chunky or platform ankle boots can add a trendy edge.
3. Consider the Length of Your Dress: If you’re wearing a shorter cocktail dress, ankle boots that hit right at the ankle can create a seamless and chic look. For a longer cocktail dress, opt for ankle boots with a bit of a heel to avoid looking frumpy.
4. Accessorize with Confidence: Complete your outfit with a statement clutch or bold jewelry to add some extra flair.

Ankle Boots That Pair Well with Cocktail Dresses:

1. Stiletto Heel Ankle Boots: These boots have a sleek and sophisticated look that pairs well with a more formal cocktail dress.
2. Lace-Up Ankle Boots: A pair of lace-up ankle boots can add some edginess to your cocktail dress.
3. Metallic Ankle Boots: For a more glamorous look, try a pair of ankle boots in a metallic finish.
4. Suede Ankle Boots: Suede ankle boots are a versatile option that can add texture and interest to your cocktail dress.

With the right styling, ankle boots can be chic and unexpected paired with a cocktail dress. Give it a try and you might just discover your new favorite outfit combination!

LBD (Little Black Dress) with Ankle Boots

The little black dress, also known as the LBD, is a timeless classic that can be worn for any occasion. One way to give your LBD a modern and edgy twist is by pairing it with ankle boots. 

Here are some tips on how to rock this look:

1. Stay Basic: Ankle boots with a classic LBD can be a simple yet elegant look. Stick to basic black ankle boots to keep the focus on the dress.
2. Go Bold: If you want to make a statement, opt for ankle boots in a bold color or pattern to contrast with your LBD. Animal prints, metallics, and bold colors like red or blue can add an extra pop to your outfit.
3. Choose the Right Length: When it comes to LBDs, the length can vary from mini to midi to maxi. Choose ankle boots that complement the length of your dress. For example, ankle boots with a midi LBD can create a chic and sophisticated look.
4. Consider the Style of the Ankle Boots: Different styles of ankle boots can give your LBD a different vibe. For a more casual look, go for ankle boots with a chunky heel or flat sole. For a dressier look, opt for stiletto-heel ankle boots or those with a sleek and streamlined design.
5. Add some accessories: To finish off your LBD and ankle boots look, add some statement accessories like a bold clutch, a statement necklace, or a wide belt.

Best Ankle Boots for LBDs

1. Black leather ankle boots: Classic black ankle boots are a timeless choice that can never go wrong with an LBD.
2. Chunky ankle boots: Chunky ankle boots can add a bit of edge to your LBD outfit, perfect for a night out.
3. Suede ankle boots: Soft and luxurious, suede ankle boots can add texture and dimension to your outfit.
4. Pointed toe ankle boots: These can create a sleek and elegant look, perfect for a dressier occasion.
5. Platform ankle boots: For those who want to add some height and drama to their LBD outfit, platform ankle boots can do the trick.

Best Ankle Boots for Dresses

Ankle booties come in various styles and designs, making them a versatile footwear choice to pair with dresses. I’ve covered some of the best ankle boots styles for each type of dress above.

However, choosing the right ankle boots to wear with dresses can be challenging, especially if you’re unsure about what style would look best.

Here is a quick breakdown of the best ankle boots to wear with dresses and their features.

1. Wedge Ankle Boots

Wedge ankle boots are a popular choice for dressing up or down. They offer height and stability while still being comfortable to walk in, making them an excellent choice for day-to-night wear. Wedge ankle boots can be paired with maxi dresses, midi dresses, and even mini dresses.

2. Chunky Ankle Boots

Chunky ankle boots are perfect for adding some edge to your dress outfit. They have a sturdy sole and a chunky heel, which provides comfort and support. They look great with mini dresses and midi dresses.

3. Platform Ankle Boots

Platform ankle boots are a fashion-forward choice that can elevate any dress outfit. They have a thick sole and a high heel, which adds height and style to your look. They look great with midi dresses and maxi dresses.

4. Stiletto Heel Ankle Boots

Stiletto heel ankle boots are a classic choice for dressing up any outfit. They have a thin and high heel, which adds a touch of sophistication and glamour to your look. They look great with midi dresses, maxi dresses, and cocktail dresses.

Places to Shop for Ankle Boots for All Budgets

Looking for the perfect ankle booties to pair with your favorite dresses? Look no further than these top places to shop for ankle boots for all budgets.

Whether you’re looking for affordable options or splurging on a designer pair, these retailers have got you covered.

1. Nordstrom Rack: If you’re looking for designer ankle boots at discounted prices, Nordstrom Rack is the perfect place to shop. You can find a variety of styles and brands at a fraction of the original price.
2. DSW: DSW is a great place to find stylish and affordable ankle boots. They have a large selection of brands and styles, so you’re sure to find the perfect pair for your wardrobe.
3. Zara: Zara is known for its trendy and fashion-forward clothing, and their ankle boots are no exception. They have a variety of styles, from classic to edgy, at affordable prices.
4. Macy’s: Macy’s offers a wide range of ankle boots from a variety of brands at different price points. You can find everything from casual to dressy styles, making it a one-stop-shop for all your ankle boot needs.
5. ASOS: ASOS offers a great selection of ankle boots at affordable prices. They have a variety of styles and colors to choose from, so you’re sure to find the perfect pair to complete your outfit.
6. Neiman Marcus: If you’re looking for high-end ankle boots, Neiman Marcus is the perfect place to shop. They carry a variety of designer brands, including Cult Gaia and Staud.

No matter what your budget is, these retailers have got you covered when it comes to ankle boots. Happy shopping!

Styling a Dress with Ankle Boots & Tights or Leggings

Ankle boots pair fabulously with all dress styles, but sometimes the weather calls for a bit more coverage. That’s where tights or leggings come in.

Here are some tips on how to style a dress with ankle boots and tights or leggings:

1. Stick with Neutral Colors: If you’re wearing a bold or patterned dress, stick with neutral-colored tights or leggings. Black or opaque tights work well with most dresses, while nude or flesh-toned tights can give the illusion of bare legs.
2. Play with Texture: If you’re wearing a simple dress, add some texture to your outfit by wearing patterned or textured tights. Try cable knit tights with a sweater dress, or sheer polka dot tights with a flirty mini dress.
3. Choose the Right Length: The length of your tights or leggings should be determined by the length of your dress. For mini dresses, opt for opaque or patterned tights that hit mid-thigh. For midi or maxi dresses, choose leggings or tights that cover your entire leg.
4. Choose the Right Boots: When it comes to ankle boots and tights or leggings, there are a few things to keep in mind. If you’re wearing thick tights, choose ankle boots with a wider opening that can accommodate the bulkier fabric. If you’re wearing leggings, opt for ankle boots with a bit of a heel to elongate your legs.
5. Accessorize appropriately: A scarf or statement necklace can add some interest to a simple dress and tights or leggings combo. A belt can also help define your waist and create a more polished look.

Styling a dress with ankle boots and tights or leggings is a great way to create a chic and practical outfit. Just remember to choose the right boots and accessories to complete your look.

How to Wear Ankle Boots with Dresses over 50

Age is just a number, and style has no expiration date. Take a moment to let that sink in.

Women over 50 can still rock a pair of ankle booties with their dresses effortlessly. Ankle boots are versatile and can be styled in different ways to suit different occasions.

Here are some tips on how to wear ankle boots with dresses over 50:

1. Opt for a comfortable pair of ankle boots: As we age, comfort becomes a priority. Look for ankle boots with a low or medium heel, a supportive footbed, and cushioning to ensure that you can wear them all day without any discomfort.
2. Choose dresses with a flattering silhouette: When choosing a dress to wear with ankle boots, look for a flattering silhouette that complements your body shape. A-line dresses, wrap dresses, and shift dresses are all great options.
3. Play with textures: Experiment with different textures to add depth and interest to your outfit. Pair a suede ankle boot with a silk dress, or a leather ankle boot with a velvet dress.
4. Accessorize: Ankle boots can be dressed up or down depending on the occasion. Add a statement necklace, a scarf, or a clutch to elevate your outfit.
5. Consider the weather: If you live in a cold climate, wear ankle boots with a dress and tights for warmth. In warmer weather, opt for ankle boots with bare legs.

Remember, there are no hard and fast rules when it comes to fashion. The most important thing is to wear what makes you feel confident and comfortable. With these tips, you can confidently rock a pair of ankle boots with your dress at any age.

Ankle Boots with Dress for Wedding Guest

Ankle boots can be a versatile and stylish choice for a wedding guest outfit, adding a touch of edge and modernity to any dress. However, there are a few things to consider when pairing ankle boots with a dress for a wedding. Here are some tips to help you get it right.

1. Check the Dress Code: Before you start putting together your outfit, make sure you know the dress code for the wedding. Some weddings may have a more formal dress code, which may require more elegant and sophisticated attire.
2. Choose the Right Ankle Boots: When it comes to ankle boots for a wedding, opt for dressier styles that are appropriate for the occasion. Avoid anything too casual, like hiking boots or combat boots, and choose ankle boots with a sleek silhouette and elegant details like suede, patent leather, or metallic finishes. Neutral colors like black, nude, or metallics are usually a safe bet, but if you want to add some color, choose ankle boots in muted tones like burgundy or navy.
3. Pair with a Flattering Dress: Choose a dress that flatters your body shape and fits the dress code of the wedding. Depending on the formality of the event, you could opt for a long maxi dress, a midi dress, or a knee-length dress. Avoid anything too revealing or too casual.
4. Accessorize Wisely: Complete your outfit with the right accessories. Keep your jewelry and bag simple and elegant, and choose a clutch that matches your dress and boots.
5. Consider the Weather: Depending on the season and location of the wedding, you may need to consider the weather when choosing your ankle boots. If it’s going to be cold or wet, opt for ankle boots with a thicker sole and waterproof finish.

Frequently Asked Questions

Ankle boots are a versatile and stylish footwear option that can be paired with a variety of dresses. But when it comes to wearing ankle booties with dresses, many people have questions about what works and what doesn’t. 

In this section, I’ll address some common FAQs about wearing ankle boots with dresses.

Is it OK to wear Flat Ankle boots With Dresses?

Yes, it is OK to wear flat ankle boots with dresses. Flat ankle boots can be a great option for creating a casual, relaxed look that’s perfect for daytime outings or weekend errands.

When choosing flat ankle boots to wear with a dress, look for styles with interesting details like buckles, studs, or fringe to add some personality to your outfit.

Can I wear ankle boots with a dress and no tights?

Yes, you can wear ankle boot with a dress and no tights. This is a great option for transitional seasons like spring and fall when the weather may not be cold enough for tights but still requires a little coverage.

If you’re wearing ankle boots with a dress and no tights, consider choosing a dress with a slightly longer hemline to balance out the look and create a cohesive silhouette. You can also experiment with different textures and fabrics, like pairing a flowy floral dress with suede ankle boots for a boho-inspired look.

Are ankle boots still in style in 2023?

Ankle boots have been a fashion staple for years, and they continue to be in style. They are versatile, practical, and fashionable.

You can find ankle boots in various materials, colors, and styles, making them a timeless and essential piece in any wardrobe.

How do you make flat boots look dressy?

Flat boots can look dressy when paired with the right dress and accessories. Here are some tips to make your flat boots look more dressy:

1. Choose the right dress: Choose a dress that has a more formal feel, such as a midi or maxi dress. Avoid wearing casual dresses like t-shirt dresses with flat boots.
2. Accessorize: Pair your flat boots with statement jewelry or a belt to cinch in your waist and add definition to your outfit.
3. Wear tights: Tights can help to elevate your outfit and add a dressier feel. You can choose opaque or sheer tights, depending on the occasion.
4. Choose the right color: Black or brown flat boots are versatile and can be paired with many dress colors. If you want to add a pop of color to your outfit, you can try wearing colorful flat boots with a neutral dress.

By following these tips, you can make your flat boots look more dressy and appropriate for various occasions.

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Remember to have fun experimenting with different combinations and finding the styles that work best for you.

Overall, there are no hard and fast rules when it comes to wearing ankle booties with dresses. It’s all about finding the styles and combinations that work for your personal style and comfort level. So have fun experimenting and creating your unique looks!

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