Best Fall Boots for Women

October 17, 2022

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

Ankle Boots

A beautiful boot that’s made for walking- the Everlane Boss Boots are great. I usually pack these for all Fall and Winter trips because I can walk miles in them. They’ve retired this style but I actually really hope they bring them back for you guys. In the meantime, this pair and this pair from another favorite brand of mine is really similar!

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!

Leather trimmed coat on Meghan Donovan of wit & whimsy

Over The Knee Boots

Ever since getting these boots in 2014 I have worn them non-stop through Fall & Winter. They also are great to travel with because they collapse down easily. The quality and comfort makes them worth the splurge. They stay up over the knee (a lot of inexpensive brands will constantly slouch down taking away from the elongating illusion over the knee boots are good for) and they’re great over jeans or with dresses. They remain one of my best investments.

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.

I have the higher heel version.

You can use code WITWHIMSY15 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.

Neutral Winter Outfit

Chelsea Boot

A low heel makes these Rag & Bone boots easy to trot around town. They are extremely well made and comfortable. They’re the perfect neutral color to wear all year round, too!

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

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.

LL. Bean Boots I @meghandono

Bean Boots

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

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.

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. 

Combat Boot

I finally found a combat boot I like with this pair by M.Gemi – a favorite brand of mine for quality shoes.

. . .

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



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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!

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