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30 knee high boots outfits | Stylish & chic ways to style tall boots

30 knee high boots outfits | Stylish & chic ways to style tall boots

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Last Updated on October 24, 2023 by Eve Dawes

What to wear with knee high boots? Sophisticated, stylish & seriously on trend ways to wear knee high boots for 2023

Knee high boots outfits can take you from day to night, through every season and are one of those Fall and Winter classics that stay in fashion every year but what do you wear with them? There are so many different ways to style knee high boots from classic to trending outfits. They’re what I look forward to the most in the colder months but how do you keep your knee high boots outfits looking fresh and fashion forward? Keep scrolling for some styling inspiration with lots of different knee high boots outfit ideas. Along with some of my favorite ways to get the most wear out of your tall boots. Whether they’re tall white boots, black boots, Uggs or killer high heels.

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Knee high boots outfits are an easy way to give all of your cooler month outfits a quick refresh, keep your feet warm and change up your style. Whether it’s a classic black knee high boots outfit, feminine, edgy, designer, statement making, dressy, everyday wear or casual look you’re wanting to create. You don’t have to spend a ton of money on tall boots to get an on trend look that still looks luxe.

Knee high boots outfit inspiration

If you’re pulling out old favorites or wondering what goes well with tall boots and is in style for 2023? I hit up Instagram, Pinterest and my favorite fashion magazines to find all of the dreamy knee high boot outfits and great options that I could find for knee high boots outfits. Looks that give for a fresh and modern take on how to wear them for 2023.

Below, are 30 gorgeous ways to wear your knee high boots this season without having to do a complete closet overhaul.

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30 ways to style tall boots / knee high boots outfits

What can I wear with knee high boots? Here’s 30 outfit ideas and ways to wear tall boots and styling tips that are seriously chic and show how versatile knee high boots are for so many different occasions and months. Whether you’re styling a black knee high boots outfit or something more colorful, here’s what’s in style right now:

Classic feminine style

Style your knee high boots under a skirt. Add black tights for extra warmth if needed during the cooler months.

Dare to bar

Mini dresses and skirts are trending for 2023 and look effortlessly stylish worn with tall boots under them.

knee high boots outfit bar legs short sweater dress

Practical everyday knee high boots outfit

For a practical, easy, everyday knee high boots outfit, wear them over skinny jeans with an oversized sweater, coordinating top or bodysuit and blazer.

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Fake some height

Create the illusion of longer legs with an all black look by wearing tall black boots over black leggings and a black top.

Work appropriate knee high boots outfit

Style mid or high heel knee high boots with a skirt suit for an office appropriate look.

Winter workwear

Under a pants suit for extra warmth during the Winter months for a stylish look.

Sexy date night tall boots outfit idea

Wear your knee high boots with your sexy mini dresses for date night.

How to style knee high boots with a sweater dress

One of my favorite looks is with a sweater dress of any length and fit. Go bare legged or add tights or even leggings for extra warmth. You can stick to monochromatic black outfits for a more slimming and elongating effect or play with color for more of a statement making ensemble.

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Euro chic

Style them with denim jeans and an oversized blazer, trench coat or long coat for Euro city chic.

Classic casual style

Style them inside straight or wide leg jeans or over skinny jeans with a fitted turtleneck sweatshirt on colder days.

Canadian Tux knee high boots outfit

Denim on denim is still trending for 2023 and looks great styled with tall boots as seen on Dua Lipa. Whether that’s denim, black or neutral boots. Have fun with making this look your own.

double denim knee high boots outfit

I’ve worn the double denim with boots look more than once and it can look so different depending on what wash of denim you wear and the type of boots you style them with.

double denim on denim outfit trend

Monochromatic moment

Create monochromatic knee high boots outfits for an elongated eternally chic look. Being petite, this is a go to look for me. It doesn’t have to be all black, bright colors like red are big for FW 2023-2024.

Retro knee high boots outfit

Wear block heel knee high boots and voluminous skirts for a retro feel. Try to keep the top more streamlined to keep the whole look balanced.

Cowgirl style

Western boots AKA cowboy boots with summer dresses is an eternally feminine and fun outfit combo for warmer months. Another way of creating the Western aesthetic is to style cowgirl boots with pretty much anything you have in your wardrobe from jean shorts to jeans.

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More ways to wear denim with knee high boots

Wear your knee high boots with a denim skirt or shorts for a casual everyday look. Maxi denim skirts are the most on trend for FW 23/24

Manor born

For an equestrian vibe style tall flat riding boots with black jeans, a blazer and sleek bun.

On trend knee high boots outfit

Style your knee high boots with any of the trending matching sets this year whether that’s skirts, shorts or pants.

How to style slouchy knee high boots

Slouchy knee high boots are in style for 2023 and look best with hemlines that hit above the boots to show them off or over skinny jeans or leggings.

how style slouchy knee high boots dress

Sophisticated lady

Wear your pencil skirts with high heeled tall boots for a sophisticated look. Keep the top fitted too for a streamlined look. Although, a little volume in the sleeves is right on trend for 2023.

How to style knee high boots with tights

Flat or heel knee high boots look great with tights for extra warmth and a mini dress or mini skirt. Just be careful if you have zippers on your boots not to snag them or wear some long socks underneath.

The French tuck

With fitted jeans and a sweater half tucked in at the front for a flattering silhouette.

Transitional season knee high boots outfit

Style them with your Spring dresses to transition from Winter into Spring. For extra warmth add a roll neck sweater under your dress for the 90’s aesthetic trending now.

Leather on leather

Don’t be afraid of leather on leather. It’s a bit like the double denim trend and can take some playing around with to get right but a leather skirt and chunky biker boots or stiletto heel boots with or without tights is seriously edgy and on trend.

leather skirt leather jacket knee high boots outfit

Keep it sleek

Keep any jeans or pants fitted so there’s no bunching of material above the top of the boots.

The perfect hemline

Make sure the hemline, especially with midi dresses, hits either a good couple of inches above or below the top of your boots but doesn’t stop where the boots start.

70’s aesthetic

Pair a suede mini skirt or sweater dress with tall white knee high boots for a retro ’70s vibe.

Casual Friday

Wear your knee high boots outfit to the office for casual Friday with a graphic tee, black skinny jeans and a tailored blazer. Swap out the tee for a crop top or silk cami for after work drinks.

Sleek knee-high boots outfit

Create a sleek knee-high boots outfit by styling them with a black shirt dress. Complete with your favorite belt and gold accessories. This is a look that can easily take you from day to night.

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The statement tall boots outfit

Add a pair of colorful or print boots to an LBD to make it pop and let the boots be the centre of attention.

Feminine knee high boots outfit

For a feminine knee high boots outfits, wear them under a satin dress dress to keep your favorite Summer slip dress on rotation. You can even wear a long sleeve t-shirt or roll neck bodysuit under it through the colder months.

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Are tall boots in style 2023

Yes, tall boots aka knee high boots are still in style for 2023. They’re a classic that will always be in fashion as they’re as practical and versatile as they are stylish. The heel and toe shape, trending color, textures and fabrics for knee high boots style and outfits trends changes year to year but they’re firmly rooted in fashion and not going anywhere.

How to style black knee high boots

Tall black boots are one of those Winter boots that will always get a ton of wear in winter. I just got a new pair of stiletto black knee high boots with a slightly square toe. They’re pretty much a wardrobe staple every woman should own as they go with almost everything in your closet. I love black suede but if you live in a wetter climate black leather’s probably the way to go.

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Patent leather boots can be fun but it goes in and out of fashion and doesn’t look as sophisticated as regular black leather. Tall black boots also have the added benefit of being easy to dress up and to take your black knee high boots outfit from day to night.

How to style tall white boots

Tall white boots are still a massive trend for 2023 and look so modern and fresh. They’re almost as versatile as black boots as they pretty much go with every color.

To make them look dressier for the evening, wear high heeled versions with a mini dress and glam accessories. They also look right on trend with sweater dresses or jeans for the day.

Pretty much any of the 30 ideas on what to wear with tall boots work just as well with any color boots.

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How to style tall Ugg boots, flat styles and riding boots

If you’re looking for a more comfortable tall boot for running around day to day or a warmer option, Wellies (yes Wellies AKA rubber boots or rain boots as seen at Chanel, Chloe and Dior), flatforms, tall Ugg boots or shearling styles are a good bet.

Uggs aren’t the most on trend boots for 2023-2024 but they’re definitely warm and comfortable. I still wear my tall Ugg boots for grocery store runs. However, my rubber Hunter boots might be coming back out again this year if it’s cold enough.

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Use code SARAHFLINT-BAEVE for $60 off the Sarah Flint black riding boots.

For a more classic style stick to black leather flat riding boots or to be totally on trend for 2023 go for a chunkier sole or pointed toed stiletto heel.

Tall flat boots can still look sophisticated and not be too casual with fitted jeans, a half tucked white button down shirt and gold accessories. Add a blazer for a dressier look. Or throw on a sweater dress for a cozy look that’s easy to dress up or down wherever you’re going.

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