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 fall 2024. 

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 last year.

T Heel Boots

The Staud Wally boots I got last Winter I wear so much thanks to being so comfortable. The T-heel are really chic and yet practical.

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

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 leather boots. This style is very akin to street style looks of the 90s and now. 

The leather is gorgeous. 

A similar look for less from Marc Fisher HERE.

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 from Everlane but there are loads of similar styles sold like this pair from another favorite brand of mine.

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.

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.

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.

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 and this pair.

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

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.

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.

Knee High Boots

A timeless style to pair with skirts and dresses, knee boots like the Loeffler Randall Goldy Boots are so stylish and so beautifully made. I can easily trot loads of steps in these and I’ve been happy with the investment for the 5+ years I have owned them. I had my cobbler stretch the shafts to make them a bit roomier in the calves.

They are also available in several other beautiful colors.

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.

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-MEGHAN 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.

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. 

Pointed Toe Boot

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

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-MEGHAN will get you 15% off your full price purchase from the brand!

Bean Boots

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

The Chic Winter Boot

Sort of like a combat 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!) 

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.

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.

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.

Shop the Styles

 

 

You May Also Like:

• French Style Fall Outfits.
• Things in My Closet I Can’t Wait to Wear This Fall.
• The Best Sezane Essentials.

This post contains affiliate links. Should you purchase something from an affiliate link, I may earn commission, at no cost to you. Thank you for your support of my work!