Skip to Content

StarFREE! Wardrobe Checklist Download + Weekly Newsletter DOWNLOAD

The 6 Best Women’s Boots for Fall

Let me start by saying you don’t “need” all of these boots.

But, having the “right” shoe on hand makes creating outfits and getting dressed quick and easy.

And this fall, there is a nice array of options, from classic and timeless, to fun and trendy.

To make it easy, I rounded up the 6 best women’s boots for fall so you have them in one place.

Many of these will look familiar since we have used them over the last several weeks in outfit posts, and there are two new styles to consider.

Remember, I recommend these items specifically, but you can also you this list as inspiration and find similar styles at different price points or that serve your specific needs.

AND look in your closet first! You might have some of these already.

The 6 Best Women’s Boots for Fall

six boots for fall


The Sock Bootie

black sock booties

Sock Bootie, $265

My personal must have for the fall is the sock bootie. 

A sock bootie is an ankle boot with a soft upper that is tight around your foot and ankle – like a sock. 

Style-wise, I really appreciate a clean boot with a slim profile that extends your leg, creating a long lean line. And this season, it works with a ton of different bottoms.

They fit beautifully under a classic full length trouser in either a straight or slim boot cut, or, for my ladies always wondering what to do with ankle* pants in the winter, these are the perfect option. 

*ankle pants – not cropped pants. 

You can also pair with a dress.

This high-low maxi from our Banana Republic Factory round-up comes to mind. 

Our featured bootie, from Coach, is kinda perfect, available in half sizes up to an 11.  These will NOT go out of style any time soon, so I’m very comfortable recommending these and these are the pair I’m going with. 

If you are feeling spendy, Stuart Weitzman knocked it out of the park with this pair

Chelsea Boot

taupe chelsea boots

Chelsea Boot, $70 

We’ve featured Chelsea Boots quiet a bit this fall.

They are a casual, comfortable and relatively inexpensive boot you can wear with jeans and leggings. Just remember, because they are heavy you want to balance them with what you wear on the top.

So go with a chunky sweater, a layered vest look or a slim-cut shacket.

I found this pair at DSW, in several neutral colors for $70

We used a version of these in a recent Outfit Formula, with jeans here, and with a simple sweater here

The Ruched Boot

black ruched boot

Ruched Boot, $139 

Next, we have one of our trendier styles, the ruched boot.

These are fun with leggings, especially faux leather ones, or paired with tights and dresses around the holidays. 

AND skinny jeans, so yeah, we’re KEEPING OUR SKINNY JEANS!

You’ll see this style everywhere, from Neiman’s to Target. 

I picked this Marc Fisher pair to highlight; they make quality, comfortable boots for the price, and I can stand in these all day. 

I think these are most versatile in black suede, but they are available in various colors. 

The Block Heel Boot

brown block heel boots

Block Heel, $228 

A block heel boot is a timeless style that works great with full length trousers and jeans. 

Above is a reader’s favorite from Ann Taylor, available in a rich pecan brown color, in a full size range. 

These are a cleaner version of a traditional chelsea boot, so they don’t have a heavy sole and offer a slimmer profile. 

You can see them here with a tie top blouse and slim boot cut jeans

The Western Boot

brown Western boots

Western, $130  

These aren’t going to be for everyone, but I think they are so fun and full of personality. 

Featured above are a pair by Dolce Vita, in dark brown, and I like the truffle suede color as a lighter option. 

Of course these are idea to pair with jeans, but they are also super cute with a dress, like a flowly maxi or a sweater dress. 

The Tall Boot

Black Tall Boots

The Tall Boot, $150  

Finally, consider bringing in a tall suede boot if you don’t already have one. 

I’m featuring this Vince Camuto pair, available in black or tan – both wonderful options. Get a black pair first. 

They are look fabulous pull over faux leather leggings, skinny jeans or with tights under a dress. 

And this pair is at reduced price, usually $230, but at DSW for $150

I bought a similar pair from Nine West a few years ago and while I don’t wear them all the time, I’m always so happy I have them, especially this time of year. 

Buy The Well Dressed Woman Workshop!

If you missed our LIVE Well Dressed Woman Workshop for Fall 2022, you can now purchase the recording and eWorkbook! 

52 Outfits in 2022!

Follow Us on Instagram!

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 6  Best Women\'s Boots for Fall

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.

Tracy Gray

Saturday 22nd of October 2022

Love this! Great ideas!


Friday 21st of October 2022

Is it true that the Ugg style boot is back?

Megan Kristel

Saturday 22nd of October 2022

They certainly are, I just don't consider a traditional UGG something I would make an outfit with. They are more like a throw on with leggings and a sweater. And the new popular style we're seeing, their Boston Clogs are currently sold out everywhere.

Marianne Rohde

Saturday 22nd of October 2022

@Andrea, I’d like to know too , I’m craving a pair of warm , comfort shearling boots to pull on without socks, with the ease of an ugg, minus the ugly caveman feel


Friday 21st of October 2022

Thank you for this great post! What type of boot would you recommend to wear with slim straight jeans? Nothing I have seems to look right. Thank you!


Saturday 22nd of October 2022

@Megan Kristel, Thank you!

Megan Kristel

Saturday 22nd of October 2022

The sock bootie is a nice option for a straight leg because the top of the boot tucks nicely under the hem of the jean. :)


Friday 21st of October 2022

I must wear flat flat boots because of balance issues (on a walker). I noticed you didn't include riding boots. Are they not in style this year? I found some flat ruched boots that I'm very excited to wear this year. I went a little crazy and bought 3 pair in navy, sand and black!!! I also own cowboy boots but don't think I can wear even this small heel any longer unfortunately!!!!!

Megan Kristel

Saturday 22nd of October 2022

You can absolutely wear a flat boot!