Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

The Best Selling Amazon Over-the-Knee Boots I LOVE

Over-the-knee boots have been popular for some time. Over in our Facebook Private Group, I get questions about them frequently. Specifically how to wear them and if they are age-appropriate.

So let’s start with the question of age. It’s simple. AGE DOES NOT MATTER. The Well Dressed Life is all about helping you achieve a modern and classic style, which is inherently timeless and ageless. I break down my philosophy on age and “appropriate” dress here.

For style inspiration, you have a lot of options. But first, lets talk about the boot. 

I wanted one that was versatile, affordable, casual and easy to incorporate into my uneventful life. 

Last December, I started to hear (unsponsored) praise for these Best Selling Amazon Over-the-Knee Boots on social media, so I decided to give them a try. 

I’ve had them for almost a year now and still highly recommend them. 

The Best Selling Amazon Over-the-Knee Boots I LOVE

Best Selling Amazon Over the Knee Boots

Boots: $45, Jeans: $80

I will never be comfortable posting pictures of myself, but thank you to everyone for being kind. I know the pictures are helpful, even though I feel like a major dork in them. 

For some context I am (almost) 41 and am 5’10. However, I found these on Pop of Pippi’s Instagram and she is petite and looks fantastic in them. So don’t be afraid to give them a try if you are petite (and follow her Insta for some great petite looks).

Are they the best quality? They do the trick, which is to let you wear a trend while it’s popular without feeling committed to it and spending a small fortune. 

They are surprisingly comfortable. The block heel gives nice support and they are not too high making them super easy to walk in. 

I paired them with the Joe’s Curvy Skinny Ankle Jean. (On sale for $80 at Nordstrom Rack – they usually retail for $189). I LOVE these. They are high waisted, with nice stretch. But the slide over any skinny jean easily. 

I’ve worn them a few different ways, usually with jeans (above) or leggings and a long cardigan (below). The key is to keep it simple. Almost think of them as pants, if that makes sense. 

This weekend I’m going to wear them with this black sweater dress from the J.Crew factory sale for dinner on Saturday (I’ll share over on Instagram).  

I original purchased the tan suede, and just ordered them in black for the holidays. I think the suede adds a richness to the look but again, has a casual vibe. 

Our Style Content is Inspired by Our Readers

Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

Some links are affiliate links, which means if you purchase via our site, we receive a small commission.

If you enjoy our content and would like to help us grow, please  follow on Instagram and join our Private Facebook Group to access more advice and exclusive in-depth conversations with other like-minded women.

Learn about our mission to help women look and feel their very best, every day, here

Sign Up for Daily Content and Receive Our Free Classic Wardrobe Checklist




The Best Selling Amazon Over-the-Knee Boots I LOVE

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

Never Miss a Post

Enter your email address below to sign up for our newsletter and get your free copy of our Wardrobe Essentials Checklist sent to your inbox.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Melissa Hawes

Thursday 12th of November 2020

First of all you look great. Not dorky at all. My question, I have a wide calf and and have to buy boots that are considered "wide calf". Are these stretchy to fit most or do you suggest something else?


Friday 21st of February 2020

If you like the Joe's Jeans curvy, try their new Hi(-rise) Honey style. I discovered a pair at my Nordstrom Rack and immediately ordered two more (one I found on their website on clearance for $18!), I loved them that much!

Megan Kristel

Friday 21st of February 2020

That's an incredible price! I discovered Joe's years ago from their Honey boot cut style - still one of my favs!

Kristin J Arnold

Friday 21st of February 2020

So...I went to amazon and there are TWO different options (I wanted black...) one is simply "Black 3" heel" and the other has "Black elastic" in the description - Help!

Megan Kristel

Friday 21st of February 2020

I would go with the black 3" heel. That's the same description as the tan ones I ordered.


Friday 21st of February 2020

I don't know who YOU think you are, but I know that I think you are amazing and awesome and real and we LOVE the pics that beautifully showcase what you're talking about in your post and what (whatever it is) looks like in real life. :)

Megan Kristel

Friday 21st of February 2020

That's incredibly kind of you, thank you :)


Friday 21st of February 2020

You're ROCKING those boots!!

Megan Kristel

Friday 21st of February 2020

LOL! Sort of ;)

Ann B Baxter

Friday 21st of February 2020

The answer to " who do you think you are?" is, a woman who has worked really hard to help other women get dressed in the morning and a woman with a successful career doing what she loves! Don't let anyone diminish you. You're doing great work! Thanks you.

Megan Kristel

Friday 21st of February 2020

Thanks Ann, you're so nice. Thanks for the support!


Friday 21st of February 2020

Thanks for sharing about these! They're even a similar price from (depending on colour). 😁 Your pictures are SO helpful too. ♡

Megan Kristel

Friday 21st of February 2020

Oh that's awesome! Thanks Beth!!