I'll say it: Booties — specifically, the most comfortable booties — are the one thing you can wear with anything in your fall/winter wardrobe. (If you wear them as often as I do, then you know the last thing you want is for them to inflict pain.) There are so many different styles out there, but the good news is, plenty meet the comfy criterion, no matter if you've got your heart set on ankle booties or a wedged pair.
The Most Comfortable Booties Have 3 Things:
When searching for the perfect booties for you, there are some important (read: functional) features to look for.
- Stacked block heels. They offer more stability than pointed heels.
- Cushioned insoles. These will help with shock absorption as you walk.
- A wider toe box and ankle opening. This is particularly key if you have wide feet and want to avoid blisters.
Keep reading to peruse the most fashionable-yet-functional booties Amazon has to offer. I've already done the research and scoured the reviews for you, so here, you'll find a variety of price points and styles guaranteed to complement your existing closet. Your feet will 100 percent thank you later... especially if you treat them to the best walking shoes for travel next.
1. The Most Comfortable Booties Considering Features & Reviews
If you're looking for easy-on/ easy-off ankle booties with the hidden support of an orthotic built inside, give this Vionic pair a try.
Why they're great: These suede booties, which come in black (pictured), greige, and olive, have a zipper with an adorable tassel detail and a modest 1.8-inch block heel. They have been pre-treated with a special protective coating to help guard against inclement weather. Even better, Vionic shoes all come with something called "Vio-Motion Support," which is special technology the brand has created to ensure all-day comfort and foot stabilization.
What fans say: "I am a teacher and on my feet all day. You pay for the comfort, but the arch support and heel cushioning is unparalleled to other shoes. These booties are super cute and I love the olive color. It's a good neutral option of you're bored of tan! Gone are the days of cheap shoes."
- Available sizes: 5 - 12 (plus some wide-width options)
2. Also Great: Splurge-Worthy Leather Booties That Offer Plenty Of Support
If you're after a premium leather look and feel, Cole Haan's Abbot slip-on boots are a solid investment.
Why they're great: Like the booties above, they have an 11-inch boot opening and side cutouts that make them suitable for wide feet (not to mention, easy to slide on and off). Additionally, they boast rubber soles and under-2-inch stacked block heels to give your feet that desired stability. Want them in another color? You can get them in two other shades — both variations of tan — but, just so you know, the block heel remains brown with each.
What fans say: "Very comfortable bootie!!! I walked in them for hours around NYC the first day I wore them and my feet felt great. I just ordered them in the British Tan because I loved them so much. I wear a size 10 and have a slender somewhat narrow foot and these worked well for me."
- Available sizes: 5 - 11
3. The Most Comfortable Waterproof Booties
Getting caught in the rain or snow while wearing leather or suede shoes is never fun. These boots by Blondo will ensure you are prepared for all weather conditions thanks to a waterproof upper and sealed seams.
Why they're great: They are the ideal shoes to pack on a .vacation to a colder, rainy climate because they can serve multiple purposes— they look stylish but are also very practile because they are waterproof. Plus, the stacked heel and rubber sole means they will stay comfortable and give you enough traction that you won't have to worry about slippery surfaces. They come in several soft suede and nubuck leather options and some of the colors are even available in wide sizes!
What fans say: "No break in time, extremely comfortable, and they are waterproof. I've owned these for less than a month and have worn them on a trip to New York and Italy, walked in them all day, every day (few of those days were very rainy) and they still look brand new. I get compliments every time I wear them."
- Available sizes: 5.5 - 13 (some sizes also available in wide)
4. A Fashionable Perforated Pair
These are the ankle boots you will love to wear during the transitional seasons of fall and spring. They are perforated, which gives them an airy feel, but also an upgrade to the traditional smooth leather styles. Dr. Scholl's is also a go-to brand for extra arch support, so you know this pick will be comfy from the start.
Why they're great: They come with a memory foam cool fit insole, are available in wide sizing, and have deeper cut outs and a tab to pull on for an easy on and off fit. Also note that several reviewers mentioned they could still wear no-show socks without having them peek out from the sides of these boots.
What fans say: "They have a little cushion inside so they are very comfortable. I liked them so much that I went back an bought the Olive ones too. They look perfect with a pair of jeans."
- Available sizes: 6 - 11 (some sizes also available in wide)
5. Comfortable Wedged Booties
For wedged heel fans, Marco Republic boots deliver on comfort, price, and style. Plus, they are crafted to be completely vegan-friendly.
Why they're great: With non-skid soles and rounded toe boxes, these booties are — spoiler! — also great for wide feet. Their wedged heel is nearly 3 inches tall, so they're the tallest on this list. However, that doesn't mean they're uncomfortable. Between the wedge and their cushioned insole, they're supportive and adorable at the same time. They come in taupe (pictured), charcoal, and black, which are all great neutrals to pair with any items in your closet.
What fans say: "Love these wedges! Really comfy and cute. I have small feet so getting shoes online is really hit or miss. I got size 5 and they fit perfectly. The inner cheetah print was an welcomed surprise, too. Definitely getting all the colors!"
- Available sizes: 5 - 11
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