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How To Wear Ankle Boots With Dresses

Ankle boots are a great way to add some edge to your outfit. They look great with skinny jeans or even leggings – and you can even team a pair of ankle boots with a cute dress for a stylish final aesthetic.

How To Wear Ankle Boots With Dresses

The trick is finding the perfect pair of boots, and knowing just how to wear them – and fortunately for you, we have the answer to both of these questions!

How To Find The Perfect Pair Of Ankle Boots

When it comes to choosing the right pair of ankle boots, there’s no such thing as too many options.

You want something that’s versatile enough to be worn in different ways but still looks good when paired with other items from your wardrobe.

If you’re looking at buying a new pair of ankle boots, here are our top tips on what to consider:


The first thing to think about when shopping for ankle boots is style. What do you like wearing with them? Do they go best with skinny jeans or more casual trousers? Are they better suited to winter or summer?

Think about your lifestyle and the kind of outfits you tend to wear most often before making any purchases and if you are planning to team your boots with dresses, keep this in mind while you are shopping for the perfect pair.


The next thing to consider when buying ankle boots is size. It’s important to buy the right size so that they fit well and don’t pinch your feet – and don’t forget to take into account whether you will be wearing socks, tights, or going barefoot, as this can impact the size you opt for.

For best results, select a pair of ankle boots that can cover all three options.


There are lots of materials available for ankle boots, including leather, suede, and faux fur.

Leather is by far the most popular option, and tends to be versatile and durable – it also looks great when paired with a number of outfits, including stylish skinny jeans and adorable dresses. 

However, leather does require extra care, so make sure you choose a quality pair of ankle boots that have been treated properly.

Suede and faux fur are also great choices, as they are easy to clean and maintain, and look fantastic when teamed with skirts and dresses.


If you’re after an elegant yet fun-looking boot, then you’ll probably want to opt for black, brown, or gray. These colors are classic and timeless and work well with almost every type of outfit.

Black and gray are particularly versatile, as they look great with everything from smart suits to denim shorts. Brown is another great choice, as it works really well with pastel shades and floral prints.


Finally, remember that you should always shop around for the best price possible. There are plenty of online retailers out there who offer great deals on high-quality products, so check their prices regularly to see if you can find a bargain.

How To Wear Ankle Boots With Dresses

How To Wear Ankle Boots With Dresses

Once you’ve found the perfect pair of ankle boots, the last step is to figure out how to wear them. Here are our top tips on how to wear ankle boots with dresses:

Matching Colors

When pairing your ankle boots with dresses, stick to similar tones, either in the boot as a whole or focusing on a detail such as the sole of the shoe.

As an example, if you have a white dress, match the shoes’ soles with white; if you have a bright red dress, match the shoes with a deep red sole.

The same goes for darker hues. If you have a navy blue dress, match the shoes to a dark shade of navy blue for a polished, pulled-together look.

Contrasting Details

While matching details between the two items is a good idea, sometimes contrast is key. This means choosing one item that stands out against the other.

In the case of ankle boots, this could mean adding a pop of color to the heel or even opting for a different material.

Mix & Mingle

Another way to mix things up is to try mixing styles within each item. For instance, you could wear a sleek pencil skirt with a pair of ankle boots, or go for a boho look with cowboy-style ankle boots and a floaty skirt.

Mixing things up is a great way to experiment with what does and does not suit you, and can go a long way towards helping you to discover and celebrate your own personal style. 

Play With Lengths

The length of your skirts can also have an impact on how ankle boots will work with the outfit, so play around with the length of your skirt before buying.

Opt for a high-waisted style for a great balance with ankle boots – this is a combination that can really elongate your legs, especially when paired with bold black tights.

Longer skirts can also work wonders with ankle boots and can be paired with tights, leggings, or bare legs. 


Accessories are a great way to finish off any outfit, and ankle boots are no exception. You don’t need to spend a fortune on accessories, but do invest in something special.

From statement necklaces to trendy scarves, accessorizing is a great way to add some personality to your ensemble without breaking the bank, and can really pull a look together – especially when you connect your boots with your bag.

Tights Versus Leggings

Tights Versus Leggings

Tights are a wardrobe staple, but they come in all shapes and sizes. They’re usually made from thicker materials than leggings, which makes them better at keeping your ankles warm.

However, if you prefer wearing leggings over tights then opt for a pair of ankle boots that has a thick sole. This will help keep your feet warm while still allowing you to move freely.

Keep It Simple

If you want to make sure that your ankle boots stand out, it’s best to keep things simple. Stick to neutral colors and patterns, and avoid anything too busy in your main outfit.

Avoid using bold prints or embellishments, as these will distract from the main focus of your outfit, and focus on choosing pieces that complement each other.

This is a great option if you are wearing boots that are brightly colored or bold – in this case, you should let the shoes speak for themselves, and keep the rest of your outfit more muted. Alternatively…

Or Highlight The Outfit

If you are opting for a pair of plain black boots, then the opposite rule can apply; there are fewer great combos than plain black boots and tights with bold, colorful skirts for some amazing contrast.

Why not try black tights and boots with a bright red skirt and a bold red lip for an eye-catching, super sophisticated final look?

Match Your Shoes To Your Skirt

When selecting your footwear, consider whether the shape of the shoe matches the shape of your skirt. A round-toe shoe will generally sit well with a straight skirt, whereas a pointed toe will look better with a flared skirt.

It is a good idea to play around with different shoes and skirt types, as these can create new and unique combinations.

Add Some Height

Ankle boots can be flat or come with a heel, and the best option will ultimately depend on your levels of comfort, the nature of your outfit, and the height of your heel.

A chunky heel can be a great way to end a shorter skirt, and will really elongate the leg, while a flat boot can be a great pairing with a longer, more boho skirt.

Try a range of heel sizes, shapes, and types with your favorite skirts and dresses to find the perfect match.

Choose The Right Fit

Ankle boots should fit snugly, but not uncomfortably.

When shopping online, check the sizing chart provided by the manufacturer to ensure that you get the correct size, and always try shoes on to make sure that they are comfortable before you commit – especially if you are planning to go barefoot inside the shoe.

Go For Comfort

The last thing you want to worry about when you’re trying to wear your ankle boots is how comfortable they are. Investing in quality leather or suede is worth it because these materials will hold up against the elements and provide long-lasting protection.

Leather also provides a bit of padding inside the boot, which helps absorb shock and prevent discomfort. In addition, choose a style that fits comfortably at first, as you may need to break them in over time.

Consider Color And Style

Color is one of the most important factors to consider when buying ankle boots. You don’t have to stick to classic black, though.

Experiment with different shades of browns, blues, grays, greens, oranges, pinks, purples, and even metallic hues.

Keep in mind that darker colors tend to work better with dark clothing, while lighter colors suit brighter outfits.

Have Fun!

Ultimately, fashion is about experimenting and having fun, so don’t be afraid to try new things, mix and match, and experiment to find your perfect look – sometimes, inspiration can come from the most unlikely of places!

Final Thoughts

A dress and ankle boot combo is a classic look that will see you through pretty much any occasion.

This is a versatile pairing that can work with a wide range of colors, styles, and materials, so why not get creative, and have some fun pulling your dream aesthetic to life.

Jenna Reign
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