Knee-High Boots: How and Where to Wear Them

Styling Knee High Boots

Welcome to boot camp! Today we’re talking all about knee-high boots – from what pants to wear with them, how to style them, and where to wear them. 


Knee-high boots seem to come and go with trends every year, but I think a classic, solid pair is a closet essential. Today, I’ll explain how to wear knee-high boots for different occasions, what pants, skirts, and dresses to wear, what socks to pair them with and so much more. I’ll break down everything you ever wanted to know about tall boots!


A few great pairs of tall boots

I just bought THESE RIDING BOOTS and they’re fantastic for narrow calves, but they also come in other widths! My suede boots are older, but THIS PAIR is similar, and my tall rain boots are HUNTER BOOTS!

We rounded up a few other similar tall boots in these three categories at all different price points!








What socks I wear with tall boots

If you want some boot socks that cover your ankles, THESE ONES are my favorite. If you want super tall ones, I don’t own THESE ONES, but they get great reviews. And if you just want a pair that covers your feet, my favorite low ones are BOMBAS, but THESE MORE AFFORDABLE ONES are fantastic too.


How to store your tall boots

Some tall boots can stand on their own, like thick rubber rain boots, but some get floppy and can’t stand on their own. I have THESE BOOT FORMS to keep my boots standing up straight and not losing their shape. I’ve had the same ones for years and they’re fantastic.


Where to wear these boots

  • the office
  • date night
  • church
  • concerts
  • girls nights
  • baby and bridal showers
  • rainy days
  • travel days when you want a nice shoe


What kind of bottoms can you wear with tall boots

  • SKINNY JEANS. They’re great with all of these kinds of boots, but I prefer them with the riding boots and rain boots, personally. Wearing the suede boots with jeans is not really my style. Try black or dark or white or mid rinse skinny jeans with your boots!
  • LEGGINGS. These work great with all three of the boots, especially with long tunic sweaters, or a sweatshirt and puffer vest with the rain boots, or a long blazer and top with the riding boots.
  • SKIRTS. I love skirts and tall boots. I don’t wear mini skirts, but knee length skirts look fantastic with all three styles, and midi skirts are amazing with the riding and suede boots.
  • DRESSES. Same as the skirts, knee length and midi (and shorter, if you wear that length) work with these boots!

DO NOT wear with wider leg jeans and stuff them into the boots, and DO NOT wear with joggers or other casual pants.


How to wear tall boots without look dated

I resisted wearing tall boots with skinny jeans for a long time cause it felt very 2010. It was like ALL I wore during 2010-2012. So any time I wore them, I felt dated. But it’s been long enough since then that I feel confident enough to wear them again. The key for me this time around is to wear them with more classic pieces, or pair them with dresses or skirts.

I’m choosing chic sweaters, or button ups and blazers with the riding boots, or pairing them with a modern and fun midi skirt, or a chic dress. I’m actually so excited to wear them this fall and winter!

With tall suede boots, I think they look more dated with jeans, so I’m wearing them mostly with dresses and skirts, in midi and shorter lengths. I’m careful with midi lengths since these are not quite so fitted to my leg and can make my ankles look bulky.

Since rain boots are more casual, I think pairing them with casual pieces is best, like leggings and a puffer vest!


How to balance tall boots in your outfits

When you wear tall boots, they can feel very bottom heavy with your outfit. So you want to make sure the top half of your outfit is balanced.

First off, choose pants that are fitted to balance the bulkier shoe.

Second, choose pieces on top that will create balance and keep attention on your top half. Try a blazer, a sweater and jacket combo, a tunic length sweater, a heavier weight sweater, a top in a bold pattern or color, a weightier coat, or a scarf on top!

All of these will help balance the heavier shoe.


Here are some outfit ideas with these three styles of boots!




Fall Tall Boots with skirt and cardigan
gray sweater dress with green coat and tall boots
dress with tall boots
dress with boots




plaid pencil skirt
gum wall seattle
red hunter boots




riding boots with midi skirt
riding boots with utility jacket
riding boots with tunic
riding boots with blazer


I hope this is helpful!

If you missed the first two days of BOOTCAMP, check out day one all about Chelsea Boots HERE, and day two all about Neutral Block Heel Ankle Boots HERE.



One Comment

Leave a Reply