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.
Stylish Sock Booties
These Inez booties are so comfortable that they are a go-to shoe for me when I go to Europe. I’ve been wearing them since 2019! I first bought the beautiful neural Ginger suede (below) and then the black calf.
You can use code MEGHAN15 for 15% off your purchase of Inez shoes.
Suede 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 (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.
Also available in cognac if you prefer.
Block Heel Ankle 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.
Look for less here.
Western Boot
I wore the Wally ankle boots so much I decided to do a minimalist take on the Western Boot trend by getting the Staud Western Wally. Also available in suede if you prefer.
I’ve seen Western-inspired boots like this pair everywhere in Europe this fall so continue to expect them to be one of the bigger boot trends for Fall 2026. Staud’s site also has a lot of gorgeous boot options for the season.
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, Marc Fisher and Dolce Vita have a lot of affordable options.
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 is another pair of knee highs I wear often with a nice, walkable heel.
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’ve owned these for three years now. This year’s version is called the Sylvie.
I also love the J.Crew Stevie Ankle boots for a kitten heel bootie. This year’s version is the Sylvie ankle boot.
The 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.
I wore the Downtown Boot so much the last year that I just got the brand’s new Phoebe Boot style that features a more square toe. The chocolate calf color is gorgeous in person and a different colorway to the other boots in my collection.
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.
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 now own three colors now – they truly are so well made and so functional yet stylish. Code WITWHIMSY10 will get you 10% off your first Freda Salvador order.
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.
It looks like they are retiring the style but I still love reaching for mine.
My Favorite Boots and Booties for Winter
I’m also in the market for a new pair of winter boots that can handle snow. I usually rely on my Freda Salvador Brooke Boot but could use a pair that has some lining. Varley has some cool looking pairs.
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.
If you’re looking for good boot socks, I recommend Calzedonia. They have so many great, well made options.
And don’t miss my guide on What Socks to Wear with What Shoes.
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
As for boots I am considering adding to my collection this year?
- These Western inspired boots from J.Crew. Or these in a gorgeous chocolate suede.
- The newest Rye shade of my beloved Inez Paz boots.
- Margaux’s new Phoebe boot. I’m also keen to get another shade of their Downtown boot.
- I’m considering this pair or this pair or this pair by Loeffler Randall whose boots have never let me down.
I also just got this pair which will be a perfect evening boot. (This pair looks similar for less).
. . .
Love my shoe collection? Shop My Bag Collection and My Favorite and Most-Worn Jeans.
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