Today I’m giving you a peek into my closet and sharing some of my favorite boots for fall and winter. Some of these I’ve had for years and some are new to me. I wear a size 5, so most of these start right there (some are from previous seasons and are no longer available in a size 5).
Fall & Winter Boot Guide
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Knee-High Boots
Knee-high boots are what I reach for when I’m looking for something to pair with a skirt, dress or pair of leggings. From a petite standpoint, knee-high boots are the hardest style to find a great fit due to the shaft height. There is also the issue of calf circumference depending on whether you need a narrow or wide fit. I personally have a narrow calf, so the styles I have to share have a slim shaft.
Steve Madden Ninny Boot
I bought these boots last year and if they were still fully stocked they would be my only pick to share. For me, they’re a perfect fit with a slim short shaft. Since I tend to only wear knee-high boots with something I want to dress up I tend to stick to a pair with a heel. I think flat knee-high boots are great too, I just don’t currently have a pair in my wardrobe. I sized up 1/2 size in these boots.
I have also tried this pair from Amazon that looks and fits almost identical to the Ninny boot.
Ways to Wear
Chelsea Boots
I wear Chelsea boots a lot during the winter. My favorite way to wear them is with leggings because its comfortable and warm, but I’ll also wear them with jeans and skirts.
Madewell Cleary Boots
I love the fit of the Cleary Boots from Madewell. They’re slim, beautiful, and durable. They don’t claim to be waterproof which is their only drawback. I just recently purchased these so I haven’t tried them in the rain just yet, but I plan to protect them with Frye Weatherproof Balm. They’re true to size for me, but run narrow. You may want to size up 1/2 size.
Ways to Wear
Winter Boots
We do get snow where I live, but it’s maybe 1-2 storms a year. So while I’ve had this pair of Nordic boots from J.Crew for a few years, they haven’t been worn a ton. They are crazy warm and keep your feet dry. They also come with two different color laces. I bought them in my true size, but you could size up for thick socks.
J.Crew Nordic Boots
Dressy Booties
I have four different pairs of booties to share in this post and I decided to seperate them into dressy and casual.
Ann Taylor Sock Booties
These booties are great for wearing with pants to work as well as with a skirt or dress. I love to wear them with tights for extra warmth. They fit slim to the leg so they can easily tuck under different pant styles and they help elongate the legs when worn with a skirt and tights. The heel is low so these are also comfortable and easy to walk in. I’m wearing them in my true size.
Ways to Wear
Marc Fisher Boots
This pair from Marc Fisher has a tall angular heel and a sleek pointed toe. They’re modern and do a great job of dressing up an outfit, I especially love to wear them with flare jeans and pants. I find them to be true to size. They’re comfortable overall, but since the heel is tall they do hurt my feet after prolonged walking or standing.
Ways to Wear
Casual Booties
All of my booties have a decent size heel (except for the chelsea boots). I personally prefer a good heel because it makes it easier to pair the boots with different types of jeans. I have two pairs that I wear often with my casual everyday outfits.
Calabria Boots
I bought these boots last year and have worn them heavily every since. They have a slim sock style shaft that fits beautifully under straight jeans and even skinny jeans. They are lighter in person than they appear online (my pictures are a closer represenation). They do run small and I recommend sizing up 1/2 size.
Ways to Wear
Madewell Mira Boots
The last pair of boots on my list is the Mira boots from Madewell. They’re a beautiful color and I like that the rounded toe makes them look a little less western than my other boots. These boots are comfortable overall but took a little bit of breaking in around the ankle. I find them to be true to size.
Ways to Wear
-Brooke
