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.
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 and skirts.
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 bought last year and this color way, too.
T Heel Boots
The Staud Wally boots I got last Winter I wear so much thanks to being so comfortable.
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 boots. The leather is gorgeous.
A similar look for less from Marc Fisher HERE.
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
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.
Suede Knee Hight Boots
And for dressier looks, I reach for these gorgeous Larroude boots. They are so comfortable and chic.
In a similar style but with a more walkable heel, I also own and love the J.Crew Stevie boots. So good for walking around.
I got so much wear out of mine from last year and can’t wait to pull them out again.
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. After wearing the Ginger color so much since 2019, I bought the black last year and now am eyeing the new Rye color, too.
You can use code WIT&WHIMSY15 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.
Mine are from 2021 so the style is not as available now but here is this season’s version.
The Downtown Boot
Margaux’s Downtown Boot features a stacked heel and a low shaft. 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. I have gotten so, so much wear out of these booties since I’ve owned them the last several years.
They also have a lower heel version if you’d prefer that.
Code SF-MEGHAN for 15% off your Sarah Flint order.
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.
Code SF-MEGHAN for 15% off your Sarah Flint order.
Lug Sole Boots
These Sam Edelman lug boots are waterproof and got so much wear last year all Fall & Winter.
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! One of my favorite and most-worn boots.
The Riding Boot
These Sarah Flint Perfect Riding Boot are so classic, so comfortable and feel like they get better with wear. Given their price point I am grateful for their timeless make and style.
Code SF-MEGHAN for 15% off your Sarah Flint order.
The Calf Boot
This stylish and sleek pair of boots is perfect with dresses and skirts.
You can use code WIT&WHIMSY15 for 15% off your first purchase when you purchase through this link.
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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.
. . .
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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