A Roundup of My Favorite Boots and Booties

September 25, 2023

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

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 thought I’d round up all my favorite pairs of boots and booties and show examples of how I style them all through Fall and all through Winter. This post is freshly updated and I also include some more styles I am eyeing and shopping for the season ahead at the end of the post.

My Favorite Boots and Booties

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 Booties

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 this color way, too.

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

Boss Boot

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!

Leather trimmed coat on Meghan Donovan of wit & whimsy

Over The Knee Boots

I have these boots in retirement right now but know they’ll come back in rotation in future years.

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

The Suede Heeled Bootie

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.

A Guide to the best of the Vail Valley I A Roundup of My Favorite Boots and Booties

Chic Snow Boots

My favorite boots for Winter, these Marc Fisher 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 now own them in two colors. 

Available in additional colors here.

Marc Fisher Izzie Snow Boots

Loeffler Randall Goldy Boots | A Roundup of My Favorite Boots and Booties

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.

If you prefer a lower heel try this pair.

Inez Boot Review I wit & whimsy

The Sleek Neutral Sock Bootie

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 but I wear those a lot less.

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

Celine Box Bag

Neutral Winter Outfit

The Walkable Neutral Bootie

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

The Round Toe Suede Ankle Bootie

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 Fall Outfit

The Downtown Boot

I also have Margaux’s Downtown Boot which is a great similar option if you prefer a pointed toe. The Chocolate Brown color is so beautiful but they have additional colors, too.

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

The Dress Bootie

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.

Sarah Flint Alexandra Boot

The Suede Low Heeled Knee High Boot

The Sarah Flint Alexandra Boot 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.

LL. Bean Boots I @meghandono

Bean Boots

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

A Road Trip Through Ireland

Hunter Boots

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

Aqua Puffer Jacket and Sam Edelman Lug Sole Boots

Lug Sole Boots

These Sam Edelman lug boots 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 Lug Boot style I recently got are the Freda Salvador Brooke Boot are so good. So lightweight, waterproof and uber comfortable. They come in a variety of colors if the brown isn’t for you!

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. 

This style is similar for less. 


Inez Mila Boot Fall Outfit

The Calf Boot

This stylish and sleek pair of boots is perfect with dresses and skirts. You can use code WITWHIMSY15 for 15% off your first purchase when you purchase through this link.

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.

. . .

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 Shoes



Other Boots I’m Loving this Season



Love my shoe collection? Shop My Bag Collection and My Favorite and Most-Worn Jeans.



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