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How to Wear a Dress with Boots

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Looking for a simple way to make your outfits more interesting? Try pairing a dress with boots—we’re diving into all the different ways to style this iconic combination.

How to wear a boho dress

One of my favorite ways to wear boots is with dresses. I especially love styling dresses this way in fall and winter, but ankle boots or cowboy boots can really be worn year round.

It’s a fun and sometimes unexpected outfit combination and looks so chic. This is also a great way get more use out of your summer dresses and expand your wardrobe without actually buying anything new.

You probably all have a few dresses and pairs of boots in your closet, so let’s see how we can style them different ways to create more cool and feminine looks with what we have in our closets already!

Types of Boots to Wear with Dresses

When it comes to pairing boots with dresses, there are so many different types of boots you can wear. Boots not only add an element of style to an outfit, but they also provide warmth and comfort during colder seasons.

From ankle boots to knee-high options, the right pair of boots can elevate the overall look of a dress and help you express your own personal style. Let’s explore the different types of boots that can be worn with dresses, providing you with options for every occasion and style preference. Whether you are looking for a casual or more formal look, there is a boot style that will perfectly complement your dress and complete your ensemble.

Dresses with Booties or Ankle Boots

boho dress long
lace holiday dress

This is probably the most common way I pair dresses with booties. There are different styles of ankle boots too—some hit right at your ankle, some hit a little higher. Some are looser and some are fitted like sock booties. Some are more casual boots and some, like leather boots, can feel more elevated.

When investing in ankle boots, opt for neutral colors that you can wear with a bunch of items in your closet—black, brown, tan—in classic and timeless materials like leather or suede.

Pairing brown or tan booties with dresses can give you a bohemian or rustic-inspired look which I personally love, while black boots or snakeskin boots can give you an edgy and trendy look. It honestly all depends in your personal style and what feels right to you.

The best part of ankle boots is that they’re extremely versatile. You can wear them with midi dresses, sweater dresses, maxi dresses and even shorter dresses that hit above the knee. Play with the proportions here. If you have a full dress, a slender style of boots can look amazing. 

Knee-High Boots and Dresses

When it comes to achieving a gorgeous boots and dresses look, the combination of knee-high boots and dresses is a classic combination. The versatility of knee-high boots allows for endless styling options, making them the perfect footwear choice to effortlessly elevate any dress. Depending on the style of your boots and dress this can feel casual enough to wear any day of the week, or elevated for a night out.

One popular way to style knee-high boots with dresses is by pairing them with a midi dress. I LOVE this look! This combination creates a perfect balance between casual and sophisticated, offering a look that is both trendy and chic. A sleek knee-high boot under a belted flowy maxi dress is so effortless and cool. It’d be a great look for work, a brunch date or a day out with friends.

striped dress, trench vest — via @TheFoxandShe

A simple crisp shirt dress with leather riding boots or leather knee-high boots feels like such a classic combination and is perfect for anyone with classic, timeless style. I can see someone wearing this to lunch or running errands. 

For those looking to make a bold statement, mini dresses paired with knee-high boots can be a fun outfit for a date night or night out with your friends. It’s flirty, sexy and fun! When pairing with a more casual dress and not as short, it can be perfect for lunch or everyday wear, even a day at the office depending on your dress code. 

Lastly, one of my favorite cozy and relaxed looks that still feels stylish is pairing knee high boots with a sweater dress. This combination creates a chic and comfortable outfit that is perfect for chilly days. The knee-high boots add a touch of sophistication to the sweater dress. Add a chic long coat over it and you’re ready to go.

Over the Knee Boots and Dresses

Over the knee boots really had their moment a few years back, but are a stylish and versatile boot that can instantly elevate any outfit.

Lowland boots with a short dress
sweater dress, lowland boots, calf hair bag, fedora — via @TheFoxandShe

One of my favorite ways to style tall boots is by pairing them with shorter dresses. The contrast between the length of the boots and the shorter hemline of the dress creates a visually appealing look that emphasizes the legs. This combination is perfect for an evening out or a chic daytime look.

However, it is also worth noting that these taller boots can be paired with longer dresses for an extra touch of warmth and sophistication. This combination works especially well during the colder months when you still want to wear dresses without sacrificing comfort. The boots provide coverage and warmth to the legs while the dress adds elegance to the overall ensemble. A maxi dress with over the knee boots looks amazing. Just aim to wear boots that are form fitting so they don’t add extra bulk to your legs.

Dresses and Cowboy Boots

Being from Texas, it’s been fun to see cowboy boots making a comeback. I think they look so cute with paired with dresses. There are knee-high cowboy boots which are more traditional, but Ive also seen ankle cowboy boots making an appearance lately and they look so fun and special!

This can be a fun way to add color and texture to your outfit with unique colors and beautiful stitching. The combination of a colorful mini dress and statement cowboy boots creates a fun and unique look that is perfect for a casual outing or a lunch date with friends.

However, this outfit combination is not limited simply to casual occasions. It can also be a great choice for more formal events, such as weddings. Pair a flowy dress with sleek and elegant cowboy boots for a bohemian-inspired wedding look that exudes style and individuality. The juxtaposition of the feminine dress and the rugged boots creates a captivating and unexpected ensemble. I love it!

Chelsea Boots & Dresses

Chelsea boots are one of the most comfortable pairs of boots that I own and look great with a midi dress or maxi dress. They have an edgy look, often with a thicker sole and I love how they look paired with a feminine dress. It’s unexpected, but really chic and if you want to test out an edgy look with out going overboard, this is the perfect way to try.

For a more polished and sophisticated look, a fitted midi dress can be paired with Chelsea boots. This combination exudes confidence and elegance.

You can opt for pairing a mini dress with Chelsea boots by layering an oversize blazer or leather jacket on top. This not only adds an element of comfort but also adds a touch of sophistication to the overall look. I’d absolutely wear this to a girls brunch or date night.

Tights with a Dress and Boots

When it comes to putting together a stylish and practical outfit for colder weather, pairing tights—sheer tights or opaque—with a dress and boots is a tried-and-true combination. Not only does it provide warmth and coverage, but it also adds a touch of femininity and versatility to your outfit.

There are several different ways to wear tights with a dress and boots, depending on your personal style and the occasion. For a classic look, opt for black tights or brown opaque tights paired with a knee-length dress and ankle boots. This combination is perfect for an office setting or a night out. 

When choosing dresses to pair with boots, consider your body shape and height. A-line dresses are flattering on most body types and can be paired with any type of boots. If you have a petite frame, opt for shorter dresses to elongate your legs and pair them with ankle boots. On the other hand, if you are tall, you can get away with wearing longer dresses with knee-high or over-the-knee boots for a more dramatic look.

What Types of Dresses to Wear with Boots—Boot & Dress Outfits to Try

Sweater Dresses with Boots

When it comes to creating a sleek, yet cozy look, sweater dresses paired with boots are a perfect combination. There are various types of sweater dresses that you can style with boots to get completely different looks

One popular option is a knee-length sweater dress. This type of dress falls just above or at the knee, allowing for a modest yet alluring look. A pair of knee-high boots worn with a dress flows seamlessly into the boots, creating a continuous line that elongates the legs. Avoid bulky or slouchy boots here and opt for something straight and sleek that balances the shape of your sweater dress. To add more definition to your waist, add a belt if you want.

ivory sweater dress outfit
sweater dress outfit for fall

For a fun and trendier look, pair a shorter sweater dress with over-the-knee boots. The form-fitting nature of the dress, combined with the height of the boots, creates a striking and elongated appearance. When your dress has less fabric and is less bulky, you can opt for boots with that have more slouch or fabric to them.

Lastly, if you have a longer sweater dress, you can pair it with ankle boots or Chelsea boots for a cool everyday look. It’s casual, but timeless and chic.

Midi Dresses with Boots

I personally think that midi dresses are the most versatile dress option for any season. Whether you’re going for a casual or formal look, midi dresses can be easily dressed up or down depending on the occasion. 

black dress outfit
dotted @abercrombie1892 dress

When it comes to boots, both short and tall options work well with midi dresses. However, I find ankle booties to be the most obvious choice as they showcase the best silhouette. The height of ankle booties allows the hem of the midi dress to fall gracefully just above or on the top of the boots, creating a balanced look.

For a chic and modern outfit, pair a black midi dress with mid-calf boots. The combination of the sleek black dress with the height of the boots adds an edgy touch to your overall ensemble. This is a great option for a night out or a more dressed-up event.

If you’re looking for a more feminine and romantic look, opt for a floral dress paired with heeled ankle boots. The delicate floral pattern of the dress combined with the height of the boots elongates the legs and adds a touch of elegance to your outfit. This combination is perfect for a springtime brunch or a garden party.

You can also wear knee-high boots with midi dresses for a chic, classic look that I personally find to be so elegant!

Maxi Dresses with Boots

Maxi dresses with boots offer a versatile and trendy look that combines effortless style and comfort. There are several ways to style maxi dresses with boots to create different aesthetics and outfits.

woodstock maxi dress

One way to style a maxi dress with boots is by pairing a floral maxi dress with ankle boots. This combination is perfect for a bohemian-inspired outfit. 

If you want to create a fun and fashionable outfit, try combining a maxi dress with chunky Chelsea boots. This juxtaposition of the feminine dress with the more casual and edgy boots creates a unique and eye-catching look. The chunky Chelsea boots provide a comfortable yet stylish footwear option that adds an unexpected twist to the outfit. Pair it with a moto jacket to add a touch of edge!

Mini Dresses with Boots

When wearing shorter dresses with boots, you can style them a bunch of different ways depending on the weather and your personal style. Ankle boots create a flattering and balanced look, making them perfect for showcasing your legs.

free people dress boho
striped dress with booties

If you’re looking for a more relaxed and casual vibe, brown or suede boots are perfect—whether they’re flat or heeled.

For a slightly edgier look, ankle or mid-calf boots in a sleek black leather can be a great option. They add a bit of drama and intrigue to a mini dress, giving off a subtle yet impactful statement.

For more of a statement, knee-high boots or over the knee boots are the way to go. These can also provided extra warmth for cooler days. When I wear boots like this, I always wear warm thermal socks underneath for a sneaky extra layer of warmth!

To winterize the look, add a pair of tights and a statement coat. This adds warmth and an extra layer of style to the outfit. Personally, I think adding any long jacket over an outfit automatically makes it feel more timeless and chic! 

I hope these tips and outfit ideas help you to get more use out of the dresses and boots in your closet and inspire you to wear them in totally different ways. 

BTW, how to wear a denim jacket with confidence, and the best white sneakers to wear with dresses.



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