I am a shoe gal through and through. I invest in my shoes and always want pairs I’ll wear again and again. With the return of boot season, I’m sharing the best fall boots for women. This post should give you ideas where to invest in your shoe wardrobe and also how to style pairs you may already own. 

Read on for a round up of the best boots that you can wear now and throughout the fall season (and beyond)! It has been freshly updated for the fall of 2025. 

Best Fall Boots For Women

The below pairs I have found to all be TTS for me and I take my usual size 7.

Ankle Boots

These booties were the best pair of shoes I bought in 2017 and remain a favorite many years later. I can go for miles and miles without any issues with these little booties and I love styling them with both jeans as seen here or with dresses.

I get compliments on them whenever I wear them and truly find myself reaching for them in Fall + Winter at least twice a week. They also come in a gorgeous cognac color I acquired two years ago.

This similar in style chocolate suede pair is gorgeous, too.

T Heel Boots

The Staud Wally boots I got last Winter I wear so much thanks to being so comfortable.

They have a variety of styles and colors of the silhouette for this year and even a knee high version I am eyeing.

Look for less here.

Kitten Heel Boots

I’d always heard good things about this brand and eyed a lot of their styles so finally invested in this on-trend, yet classic pair of oh so comfortable and walkable boots. The leather is gorgeous. 

If you prefer a block heel, try these.

A similar look for less from Marc Fisher HERE.

I also love the J.Crew Stevie Ankle boots for a kitten heel bootie. 

Chelsea Boots

Chelsea boots are great because they often allow for loads of miles but are stylish to go with most of your Fall & Winter outfits. Better yet? They hold up in rain and light snow, too if you buy a quality pair.

The style shown above I’ve owned for years from Everlane and are no longer available but there are loads of similar styles sold like this pair from another favorite brand of mine.

Or, a bit more western in style, I like the look of this pair, too.

Pointed Toe Suede Boot

If you prefer a pointed toe, the Margaux Downtown Boot may also be perfect for you. Margaux’s Downtown Boot features a stacked heel and a low shaft. The Chocolate Brown color is so beautiful but they have additional colors, too.

Or consider the J.Crew Piper boots. A great suede pull on boot.

Lug Sole Boots

These Sam Edelman lug boots are equal parts stylish and practical. They are waterproof and got so much wear last year all Fall & Winter. They sold out early in the season but they are restocked for now so grab ’em if interested.

This chocolate suede color they just introduced are so good.

And the style I get so much wear out of are the Freda Salvador Brooke Boot that are much more lightweight than the Sam Edelman ones. But also are waterproof! Practical and yet so stylish.

I added the black leather pair to my rotation last year, too.

The Riding Boot

I looked for what felt like years to find the perfect riding boot. I wanted something unbranded (read: no logos!), something that felt really timeless, was comfortable and was slim. When I saw these Khaite Riding Boots I loved them but not at their price point. But years ago by some stroke of luck and a tip from a friend, they were briefly marked down on Saks during one of their sales and I scored them for over 40% off. 

I took my usual size 37 in these and I did have to bring them to my cobbler to have the shafts stretched as I found them rather narrow.

A good look for less I recently spotted is this pair and this pair.

Shortly thereafter the Khaite find, I also was gifted the Sarah Flint Riding Boot for a collabroation and I actually wear them even more as they are less heavy and a bit more feminine in style which makes them more wearable with more of my wardrobe. The small heel on them makes them perfect for dresses and skirts in particular.

Code SF-MEGHAND15 will get you 15% off your full price purchase from the brand!

The Stylish Sock Bootie

These Inez booties are so comfortable and I love the perfect neutral color of them in the Ginger Suede. A full review can be found here. I wore the Ginger so much since I got them back in 2019 that I bought the Black last year and plan to buy the Rye this year.

You can use code MEGHAN15 for 15% off your purchase of Inez shoes.

The Leather Knee High Heeled Boot

A timeless style to pair with skirts and dresses, the Loeffler Randall Goldy Boots are so stylish and so beautifully made.

They are also available in a gorgeous cognac color. And finally a wide calf version, too!

If you prefer a lower heel try this pair.

Suede Knee Hight Boots

And for dressier looks, I reach for these gorgeous Larroude boots. They are so comfortable and chic.

I also have the beautiful J.Crew Stevie boots with a smaller heel in suede. They are so comfortable and some of my most worn boots.

A similar style with a lower heel and a zipper, the Sarah Flint Alexandra Boot. These have a low tortoise heel that’s as striking as it is practical so you can really trot in these boots. They’re slim to the leg making them very flattering and have a hidden zipper so the boot doesn’t get bulky. 

Code SF-MEGHAND15 will get you 15% off your full price purchase from the brand!

I found a similar look for less in this pair by Sam Edelman.

Lastly, I also love the soft brown color of this pair by Inez.

Dress Boots

The Sarah Flint Dress Bootie is the quintessential bootie for dressier occasions all Fall and Winter. Designed with extra foot padding these are comfortable and just so beautifully made. They also have a lower heel version if you’d prefer that.

Code SF-MEGHAND15 will get you 15% off your full price purchase from the brand!

I love the look of this pair from Inez, too.

Bean Boots

The classic boots that are essentially a requirement for us NorthEasters!

Alternatively, Varley just launched boots and they are chic with a capital C. This pair looks similar to a pair from The Row my friend has, these look perfect for winter days and these could be styled a myriad of ways.

Rain Boots

I have both the High Gloss classic Hunter Rain Boots and the packable boots that are perfect for travel where you’ll inevitably run into rainy Fall days.

The Shaft Boot

A stylish vintage boot perfect for pairing with skirts and dresses – meet the Inez Mila Boot.

You can use code MEGHAN15 for 15% off your purchase of Inez shoes.

Western Boot

Pointed toes and embroidered details make a nice change and embrace an on-trend style. I’m not one to wear cowboy boots so I lean into this style in a minimal bootie. 

This pair fits the bill.

. . .

Most of these pairs of boots I’ve had for years. I take excellent care of my shoes but I also walk in them a lot living in New York. It’s why I invest in pairs and in brands that I know put quality first. So while the above may seem pricey, they have served me well and for much longer than when I buy less expensive boots.

Shop the Styles

You May Also Like:

• French Style Fall Outfits.
• Things in My Closet I am Wearing this Fall.
• The Best Sezane Essentials.

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