35 Cute dresses to wear with thigh high boots

By Shevon Clay / Updated on November 15, 2018
Dress and boots combination is ideal for many different occasions. Want to see more? We have prepared many outfits for you to get inspired. #bootsoutfits #highboots

Is there anything better than the dress-boots combinations on cold winter days?

Remember – always make yourself cozy and warm rather than stylish. We have turned to some of the best dress-and-thigh-high-boots outfit ideas, to show you that going out from your jeans in winter is easy! Whether they are knit or ruffle dresses, you will look fantastic when pairing them with over-the-knee boots. Let’s start, shall we?

All-red-everything outfits never seemed easier to style, right? The sweater dress is a perfect piece for winter - stylish and warm at the same time! #highbootsPhoto: pinterest.com

All-red-everything outfits never seemed easier to style, right? The sweater dress is a perfect piece for winter – stylish and warm at the same time!

Grey suede surprisingly goes pretty well with any other shade. It is almost like you are wearing black. Style your thigh-high boots with the casual soft pink dress and add a grey coat over it. #highbootsPhoto: gurl.com

Grey suede surprisingly goes pretty well with any other shade. It is almost like you are wearing black. Style your thigh-high boots with the casual soft pink dress and add a grey coat over it.

Lovely colors of fall, such as orange, brown, and beige work fantastically with the boots in grey. The dress like this provides you with comfort, while boots make you feel warm. #highbootsPhoto: Instagram/@looklovelyliving

Lovely colors of fall, such as orange, brown, and beige work fantastically with the boots in grey. The dress like this provides you with comfort, while boots make you feel warm.

Wearing button-down as a dress is a great idea. If you want to make this look even more interesting, layer it with a long camel coat. #highbootsPhoto: pinterest.com

Wearing button-down as a dress is a great idea. If you want to make this look even more interesting, layer it with a long camel coat.

Tall boots look amazing if you style them with such effortless pieces. The dress in emerald paired with burgundy boots is the perfect choice for everyday wear. #highbootsPhoto: wendyslookbook.com

Tall boots look amazing if you style them with such effortless pieces. The dress in emerald paired with burgundy boots is the perfect choice for everyday wear.

Bohemian vibes never go out of style. Tribal prints, geometric patterns as well as pom poms are more than welcome even in winter time. #highbootsPhoto: pinterest.com

Bohemian vibes never go out of style. Tribal prints, geometric patterns as well as pom poms are more than welcome even in winter time.

If you don’t own even one floral dress in your closet, I suggest to buy it now. It styles perfectly with thigh-high boots, so you can wear it even as your workwear. #highbootsPhoto: theivorylane.com

If you don’t own even one floral dress in your closet, I suggest to buy it now. It styles perfectly with thigh-high boots, so you can wear it even as your workwear.

You can’t escape from all-black-everything outfits. They are timelessly sophisticated and looking polished all the time. #highbootsPhoto: pinterest.com

You can’t escape from all-black-everything outfits. They are timelessly sophisticated and looking polished all the time.

Warm orange shade is one of the best fall shades. The dress is accessorized with flowers and styled with over-the-knee boots. Perfect for sunny fall days, right? #highbootsPhoto: outfitism.com

Warm orange shade is one of the best fall shades. The dress is accessorized with flowers and styled with over-the-knee boots. Perfect for sunny fall days, right?

Pinafore dresses make everything easier. You can layer them with a classy button-down below and feel cozy with tall boots that match the color of the dress. #highbootsPhoto: pinterest.com

Pinafore dresses make everything easier. You can layer them with a classy button-down below and feel cozy with tall boots that match the color of the dress.

Wrapped dresses should be your number one for winter time. Why? First of all, they are versatile, you can wear them with any other item - jacket, long coat or trench. #highbootsPhoto: pinterest.com

Wrapped dresses should be your number one for winter time. Why? First of all, they are versatile, you can wear them with any other item – jacket, long coat or trench.

Look like this is perfect for everyday wear, the block heels will provide you will comfort all day long.

You can't escape floral print even on the coldest days. However, floral dresses are so chic that you can style them for every occasion. With these lovely knee-high boots, you can be sure your look will be upgraded. It has straight cut which seems flattering, while the yellow color is always welcome in our closets. #highbootsPhoto: pinterest.com

You can’t escape floral print even on the coldest days. However, floral dresses are so chic that you can style them for every occasion. With these lovely knee-high boots, you can be sure your look will be upgraded. It has straight cut which seems flattering, while the yellow color is always welcome in our closets.

Maybe you are not aware, but slouchy boots are a pretty big trend at the moment. Since they have appeared on Isabel Marant show in Paris fashion week, they didn't stop to be the object of craving for many It girls. You can style them for everyday events, as well as for a night out. These are perfect boots with a strong vibe from the '80s.

Maybe you are not aware, but slouchy boots are a pretty big trend at the moment. Since they have appeared on Isabel Marant show in Paris fashion week, they didn’t stop to be the object of craving for many It girls. You can style them for everyday events, as well as for a night out. These are perfect boots with a strong vibe from the ‘80s.

One of the leading print trends this fall and winter is animal print. So if you were wondering why you see snakeskin, croc, and leopard print everywhere - that is the answer. You can look trendy if you choose animal printed instead of buying classic black thigh-high or knee-high boots. Pairing them is easy - style them with the white button-down dress and voila! #highbootsPhoto: pinterest.com

One of the leading print trends this fall and winter is animal print. So if you were wondering why you see snakeskin, croc, and leopard print everywhere – that is the answer. You can look trendy if you choose animal printed instead of buying classic black thigh-high or knee-high boots. Pairing them is easy – style them with the white button-down dress and voila!

Combining sporty and casual items can be exciting, while these outfits are very comfortable to wear. The long bomber jacket is styled with a sweater dress. This combination is rounded off with lovely knee-high boots. You can wear this look when going out for lunch, coffee or a casual stroll around city blocks. #highboots

Combining sporty and casual items can be exciting, while these outfits are very comfortable to wear. The long bomber jacket is styled with a sweater dress. This combination is rounded off with lovely knee-high boots. You can wear this look when going out for lunch, coffee or a casual stroll around city blocks.

The off-the-shoulder dress looks very flowy and summerish. However, while it is still early fall, you can mix this dress with burgundy knee-high boots. These boots have block heels which automatically make them the most comfortable in the world. You can add a shiny accessory, such as a crossbody bag. #highbootsPhoto: bloglovin.com

The off-the-shoulder dress looks very flowy and summerish. However, while it is still early fall, you can mix this dress with burgundy knee-high boots. These boots have block heels which automatically make them the most comfortable in the world. You can add a shiny accessory, such as a crossbody bag.

Burgundy look with a hint of rose looks pretty perfect for both casual and elegant wear. This chunky knit will keep you comfortable and very cozy, be sure in that. #highbootsPhoto: wendyslookbook.com

Burgundy look with a hint of rose looks pretty perfect for both casual and elegant wear. This chunky knit will keep you comfortable and very cozy, be sure in that.

Unlike tall suede boots, slouchy boots give you a retro look from the '80s. That is not a bad thing though - wear them with a short flower dress for a night out or cocktail party. #highbootsPhoto: shopstyle.com

Unlike tall suede boots, slouchy boots give you a retro look from the ‘80s. That is not a bad thing though – wear them with a short flower dress for a night out or cocktail party.

Buying boots in sapphire blue might seem like a bad idea. However, they will add vibrancy and that ‘cool’ vibe to all your looks, even the most casual ones. #highbootsPhoto: wendyslookbook.com

Buying boots in sapphire blue might seem like a bad idea. However, they will add vibrancy and that ‘cool’ vibe to all your looks, even the most casual ones.

Chic and boho - this look is appropriate to wear during all seasons. Accessorize your dress with a wide belt and add tall boots. #highbootsPhoto: pinterest.com

Chic and boho – this look is appropriate to wear during all seasons. Accessorize your dress with a wide belt and add tall boots.

Comfortable looks like this one are ideal for everyday wear. Tall boots in combination with printed blue and white button-down dress seem like very comfy and stylish mix. #highbootsPhoto: teetharejade.com

Comfortable looks like this one are ideal for everyday wear. Tall boots in combination with printed blue and white button-down dress seem like very comfy and stylish mix.

If you opt for an off-the-shoulders dress, don’t forget to drape a coat over. However, thigh-high boots will provide you with a lot of warmth and comfort. #highbootsPhoto: pinterest.com

If you opt for an off-the-shoulders dress, don’t forget to drape a coat over. However, thigh-high boots will provide you with a lot of warmth and comfort.

Orange lace dress looks very flowy and fashionable. If you want to wear it on a cold fall or winter days, then style it with grey thigh-high boots. #highbootsPhoto: hellofashionblog.com

Orange lace dress looks very flowy and fashionable. If you want to wear it on a cold fall or winter days, then style it with grey thigh-high boots.

Grey knit dress is combined with a tailored vest in the same shade. You don’t need to choose between wearing tights or leaving your legs bare - tall boots will keep you warm all the time. #highbootsPhoto: hellofashionblog.com

Grey knit dress is combined with a tailored vest in the same shade. You don’t need to choose between wearing tights or leaving your legs bare – tall boots will keep you warm all the time.

This supermodel pairs wrap dress with thigh-high boots. The outfit seems effortless, casual, and pretty comfortable. #highbootsPhoto: pinterest.com

This supermodel pairs wrap dress with thigh-high boots. The outfit seems effortless, casual, and pretty comfortable.

Who has said that navy and black doesn’t work together? Soft materials like velvet and corduroy are ideal for cold fall and winter days. #highbootsPhoto: ecstasymodel.com

Who has said that navy and black doesn’t work together? Soft materials like velvet and corduroy are ideal for cold fall and winter days.

The straight cut dress can provide you with a big dose of comfort. That is why, when combined with tall boots, it becomes a perfect dress for an everyday look. #highbootsPhoto: pinterest.com

The straight cut dress can provide you with a big dose of comfort. That is why, when combined with tall boots, it becomes a perfect dress for an everyday look.

If you were following trends, then you have probably have seen that one of the main prints this season is snakeskin, i.e., animal print. Believe it or not, printed snakeskin dresses are easy to style with black over-the-knee boots. #highbootsPhoto: fashiontasty.com

If you were following trends, then you have probably have seen that one of the main prints this season is snakeskin, i.e., animal print. Believe it or not, printed snakeskin dresses are easy to style with black over-the-knee boots.

As a businesswoman, you need to have a dress like this in your wardrobe. Then you can style it with a tailored blazer and thigh-high boots. #highbootsPhoto: thegirlfrompanama.com

As a businesswoman, you need to have a dress like this in your wardrobe. Then you can style it with a tailored blazer and thigh-high boots.

Make sure to have at least one poncho in your closet. It will keep you warm and very fashionable at the same time - wear it with jeans and brown thigh-high boots. #highbootsPhoto: fenzyme.com

Make sure to have at least one poncho in your closet. It will keep you warm and very fashionable at the same time – wear it with jeans and brown thigh-high boots.

Moto leather jacket, flower dress, and thigh-high boots - all these items are must-haves in your wardrobe. And this is how they look when mixed. #highbootsPhoto: veja-du.de

Moto leather jacket, flower dress, and thigh-high boots – all these items are must-haves in your wardrobe. And this is how they look when mixed.

Add cowboy vibes to your daily outfits, by wearing denim dress with brown suede details. #highbootsPhoto: memorandum.com

Add cowboy vibes to your daily outfits, by wearing denim dress with brown suede details.

Red slouchy boots a la Isabel Marant perfectly work with an oversized sweater dress. If you are looking for something to wear on a daily basis, then this should be your first choice. #highbootsPhoto: veja-du.de

Red slouchy boots a la Isabel Marant perfectly work with an oversized sweater dress. If you are looking for something to wear on a daily basis, then this should be your first choice.

Grey and white make perfect winter combination, without making you look like a snowball. If you prefer interesting accessories, add fluffy handbag. #highbootsPhoto: veja-du.de

Grey and white make perfect winter combination, without making you look like a snowball. If you prefer interesting accessories, add fluffy handbag.

Jewel colors are perfect to wear on cold winter days. They match with brown and black - make sure your dress is comfy and drape the floral coat over. #highbootsPhoto: memorandum.com

Jewel colors are perfect to wear on cold winter days. They match with brown and black – make sure your dress is comfy and drape the floral coat over.


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