Best Fall Boots for Women

October 24, 2023

Best Boots for Women

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)!

Best Fall Boots For Women

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

Teddy Coat and Kick Flares on Meghan Donovan | A Roundup of My Favorite Boots and Booties

Sock 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 and in leather.

Everlane Denim Guide & Boss Boots | A Roundup of My Favorite Boots and Booties

Chelsea Boots

These Boss Boots are comfortable enough for loads of miles but also stylish to go with most of your Fall & Winter outfits. Better yet? They hold up in rain and light snow, too.  This style is no longer available but there are loads of similar styles sold like this pair and this pair from another favorite brand of mine.

Aqua Puffer Jacket and Sam Edelman Lug Sole Boots

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.

Freda Salvador Boot Fall Outfit

Another style I recently got are the Freda Salvador Brooke Boot that are much more lightweight than the Sam Edelman ones. But also are waterproof!

Rag & Bone Rover Boots

The Comfortable Suede Bootie

This timeless style of bootie is so versatile and I think investing in a pair comfortable enough to walk all over town in is so worthwhile. (So many less expensive styles exist but they are painful!) These Rag & Bone boots are my favorites. They go well with jeans as well as skirts and dresses in the Fall. Other colors are available, too.

Sezane Fall Boots

The Casual Knee High Boot

I wanted to add a chic, yet casual low heeled boot to my favorite boots this season and these Sezane Adele Boots fit the bill. They are beautifully made, comfortable to walk in and have a looser calf shaft so I didn’t have to have them adjusted at all.

Khaite Riding Boot

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 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 from & Other Stories and this pair by Sam Edelman.

Sarah Flint Riding Boot

I also just got the Sarah Flint Riding Boot which I love for the small heel on them making them perfect for dresses and skirts in particular. Code SARAHFLINT-MEGHAN will get you 15% off your first pull price purchase from the brand!

Barbour Icons Collection I 125th Anniversary I wit & whimsy

Heeled Boots

These heeled Marc Fisher boots are so good for Fall and Winter that I now own them in two colors. They look as good with jeans as they do dresses and are comfortable for toting around town.

Inez Boot Review I wit & whimsy

Another style I own and love – these Inez booties are so comfortable and I love the perfect neutral color of them. A full review can be found here.

You can use code WHIMSY15 for 15% off your purchase of Inez shoes.

Paris Winter Outfit Matching Set with Loeffler Randall BootsKnee High Boots

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.

If you prefer a lower heel try this pair.

Sarah Flint Alexandra Boot

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 SARAHFLINT-MEGHAN will get you 15% off your first pull price purchase from the brand!

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

Fall Neutrals I The Margaux Boot | wit & whimsy

Round Toe Boot

The Margaux Boot was designed for ease of wear – a low, walkable heel and a timeless almond-toe that makes them elegant and easy to wear with dresses or skirts or with jeans

Margaux Downtown Boot

Pointed Toe Boot

If you prefer a pointed toe, the Margaux Downtown Boot is perfect for you.

Sarah Flint Dress Bootie | A Roundup of My Favorite Boots and Booties

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 SARAHFLINT-MEGHAN will get you 15% off your first pull price purchase from the brand!

LL. Bean Boots I @meghandono

Bean Boots

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

A Guide to the best of the Vail Valley I wit & whimsy

The Chic Winter Boot

My favorite boots for Winter, these Marc Fisher Izzie boots are as stylish as Winter boots come. They are warm, so chic and crazy comfortable. They sell out every single season for good reason (I’ve already seen them sell out once this season!) I just bought them in the suede version as I know I’ll wear those a lot, too (see below!) Original post here.

Marc Fisher Izzie Snow Boots

A Road Trip Through Ireland

Rain Boots

I have both the High Gloss classic Hunter Rain Boots and the packable boots that are perfect for travel (seen above). A necessity for rainy Fall days.

Inez Mila Boot Fall Outfit

The Shaft Boot

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

You can use code WHIMSY15 for 15% off your purchase of Inez shoes.

Madewell Heeled Western Booties

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. 


. . .

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.

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comments +

  1. Pearl says:

    Lovely post! Where did you get the shorts in the first picture? I have been trying to find “fall shorts” that I can wear with tights and have had no luck!

  2. Joanna says:

    Love the Marc Fisher Issie boot but there are so many bad reviews regarding the grommets breaking off. Obviously you have had no problems. Hmmm

    • Meghan says:

      Oh no! I’ve not heard that but also mine are from 2019 and 2020 so maybe they changed how they are made? But they look the same still so that’s a real bummer! Definitely hasn’t been my experience.

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