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 along with sharing two newer pairs I’ve recently picked up!
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 Boots
These booties are one of my favorite boots and booties. They 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 two years ago.
This similar in style chocolate suede pair is gorgeous, too.
This is the other sock boot I wear constantly in Fall and Winter.
These Inez booties are so comfortable and I love the perfect neutral color of them in the Ginger Suede. A full review can be found here. I wore the Ginger so much since I got them back in 2019 that I bought the Black last year and plan to buy the Rye this year.
You can use code MEGHAN15 for 15% off your purchase of Inez shoes. I just got the newly released Paz Leather boot!
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.
Look for less here.
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 last year and ended up wearing them so, so much. The leather is gorgeous. They have so many styles worth browsing.
If you prefer a block heel, try these.
A similar look for less from Marc Fisher 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 several other colors. I’ve been wearing Loeffler Randall boots for years and years and think the quality is so wonderful.
If you prefer a lower heel try this pair.
The Low Heeled Leather Knee High
And this pair and this pair I just got in Fall of 2025 to add to my rotation. (I got this pair after seeing a girlfriend wear them a lot and I was always asking her about them so decided a year+ later it was time to finally invest!)
Suede Knee Hight Boots
And for dressier looks, I reach for these gorgeous Larroude boots. They are so comfortable and chic.
And with a lower heel, I also love the soft brown color of this pair by Inez.
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.
I also love the J.Crew Stevie Ankle boots for a kitten heel bootie.
The Pull On 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 largely no longer available but they have so many great looking pairs of boots at the moment for the coming months.
New for me this season, I just picked up these boots that look gorgeous and are 1/3 of the price of a designer boot I’d been eyeing for a few years.
Or consider the J.Crew Piper boots. A great suede pull on boot.
The Margaux Downtown Boot
If you prefer a pointed toe, the Margaux Downtown Boot may also be perfect for you. 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. These don’t get loads of wear for me due to the color choice I made but I do love them.
The Dress Bootie
The Sarah Flint Dress Bootie is my 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.
You can use code SF-MEGHAND15 for 15% off your Sarah Flint order for a limited time.
Lug Sole Boots
I get so much wear out of are the Freda Salvador Brooke Boot that are so lightweight but also water resistant. Practical and yet still stylish.
I added the black leather pair to my rotation last year, too.
I wear them with these socks, FWIW.
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.
You can use code SF-MEGHAND15 for 15% off your Sarah Flint order for a limited time.
The Calf Boot
This stylish and sleek pair of boots is perfect with dresses and skirts.
You can use code MEGHAN15 for 15% off your first purchase when you purchase through this link.
My Favorite Boots and Booties for Winter
I’m also in the market for a new pair of winter boots that can handle snow. Varley just launched boots and they are chic with a capital C. This pair looks similar to a pair from The Row my friend has, these look perfect for winter days and these could be styled a myriad of ways.
And J.Crew has great boot socks in a variety of styles!
I’ve had most of these pairs of my favorite boots and booties 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 My Favorite Boots and Booties Collection
Other Boots and Booties I’m Loving This Season
Love my shoe collection? Shop My Bag Collection and My Favorite and Most-Worn Jeans.
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