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.
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.
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!
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.
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.
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.
The Leather Knee High Heeled Boot
If you prefer a lower heel try this pair.
The Sleek Neutral Sock Bootie
I have the higher heel version.
You can use code WITWHIMSY15 for 15% off your purchase of Inez shoes.
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!
The Round Toe Suede Ankle Bootie
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.
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.
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.
The classic boots that are essentially a requirement for us NorthEasters!
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.
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!
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.
The Calf Boot
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.
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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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Shop the Shoes
Other Boots I’m Loving this Season
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