Now Reading
30 Ways to Style Tall Boots | Stylish & Chic Knee High Boot Outfit Ideas

30 Ways to Style Tall Boots | Stylish & Chic Knee High Boot Outfit Ideas

ways wear tall boots outfit style ideas glamour gains

What to wear with tall boots? Sophisticated, stylish & seriously on trend ways to wear knee high boots for 2021-2022

Tall boots or knee high boots are one of those Fall and Winter classics that stay in fashion every year. The heel and toe shape changes but the length stays the same. I love boots, ankle, knee high, thigh high, they’re what I look forward to the most in the colder months. I have a pair of Chloé slouchy boots I’ve resoled more times than I can count as I’ve pulled them out every Winter for the last 15 years! But how do you keep them looking fresh and fashion forward? Keep scrolling for some styling inspiration to get the most wear out of your tall boots. Whether they’re tall white boots, tall black boots, tall ugg boots or killer high heels.

knee high boots blogger glamour gains wearing designer chloe

Tall boots 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 that’s classic, edgy, designer, statement making or feminine. You don’t have to spend a ton of money on tall black boots to get an on trend look that still looks luxe.

If you’re pulling out old favorites or wondering what goes well with tall boots and is in style for 2021 I hit up Instagram, Pinterest and my favorite fashion magazines to find all of the dreamy knee high boot outfits I could find. For styles that give for a fresh and modern take on how to wear them for 2021. Below, are 30 gorgeous ways to wear them this season without having to do a complete closet overhaul.

View this post on Instagram

A post shared by Victoria (@inthefrow)

30 ways to style tall boots / knee high boots

What can I wear with knee high boots? Here’s 30 ways to wear tall boots that are seriously chic and show how versatile tall boots are.

  1. Style your tall boots under a midi skirt
  2. Midi dresses are trending for 2021 and look effortlessly stylish with boots worn under them.
  3. Over skinny jeans for a practical everyday look.
  4. Create the illusion of longer legs by wearing black boots over black leggings and a black top.
  5. With a skirt suit for an office appropriate look.
  6. Under a pants suit for extra warmth.
  7. Wear your knee high boots with your sexy mini dresses for date night.
  8. One of my favorite looks is with a sweater dress of any length and fit.
  9. Style them with jeans and an oversized blazer for Euro city chic.
  10. With jeans and a fitted turtleneck sweatshirt on colder days.
  11. Denim on denim is still trending for 2021 and looks great styled with tall boots.
  12. Create monochromatic looks for an elongated eternally chic look. Being petite, this is a go to look for me.
  13. Block heels and voluminous skirts for a retro feel.
  14. Western boots with ruffled skirts isn’t the most on trend for 2021 but eternally feminine and fun.
  15. Wear your knee high boots with a denim skirt for a casual everyday look.
  16. Tall flat boots with black jeans, a blazer and sleek bun for an equestrian vibe.
  17. Flat tall boots always make mini skirts and dresses look more seasonal.
  18. Slouchy boots are in for 2021 and look best with hemlines that hit above the boots to show them off.
  19. 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 2021.
  20. Flat or heel knee high boots look great with tights for extra warmth and a mini dress or mini skirt.
  21. With fitted jeans and a sweater half tucked in at the front for a flattering silhouette.
  22. With your Spring dresses to transition from Winter into Spring.
  23. Don’t be afraid of leather on leather. A leather skirt and chunky biker boots with or without tights is seriously comfortable and on trend.
  24. Keep any jeans or pants fitted so there’s no bunching of material above the top of the boots.
  25. Make sure the hemline hits either a good couple of inches above or below the boots but doesn’t stop where the boots start.
  26. Pair a suede mini skirt or sweater dress with tall white boots for a retro ’70s vibe.
  27. Wear your tall black boots 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.
  28. Pair tall black boots 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.
  29. Add a pair of colorful or print boots to an LBD to make it pop and let the boots be the centre of attention.
  30. Under a satin dress dress to keep your favorite Summer slip dress on rotation. You can even wear a long sleeve t-shirt under it through the colder months.

View this post on Instagram

A post shared by Hailey Rhode Baldwin Bieber (@haileybieber)

Are tall boots in style 2021

Yes! Tall boots aka knee high boots are still in style for 2021. 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 change year to year but they’re firmly rooted in fashion and not going anywhere.

How to style tall black boots

Tall black boots are one of those Winter boots that will always get a ton of wear in winter. 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.

Patent 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 take you from day to night.

One of the best fashion tips we’ve learned over the years is: The shorter your hemline, the lower your heel.

Pure Wow

How to style tall white boots

Tall white boots are a massive trend for 2021 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.

knee high boots white fashion blogger glamour gains Vegas

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, tall Ugg boots or shearling styles are a good bet. Uggs aren’t the most on trend boots for 2021 but they’re definitely warm and comfortable. I still wear my tall Ugg boots for grocery store runs.

black knee high boots fashion blogger winter 2021 2022

For a more classic style stick to black leather flat riding boots or to be totally on trend for 2021 go for a chunkier sole.

Flat tall 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.

tall black boots sarah flint

Follow for more daily style inspiration

More Fall & Winter fashion

© 2022 Eve Dawes LLC | Glamour and Gains. All Rights Reserved


Privacy Policy


Scroll To Top