Unless otherwise specified, all sizes in this post are listed in women's.
1. Square-toe boots guaranteed to become one of your new favorite pair of boots to wear in the fall. They're sleek, chic, and give juuust enough height that you feel tall and mighty without compromising support.
Promising review: "Very comfy and great looking boots! Just like the picture. The heel height makes me taller but isn’t too steep to walk naturally in. Zipper is smooth to pull up and it stays up and doesn’t creep down over time. Overall very happy with this purchase." —Rebecca Henry
Get them from Amazon for $69.90+ (available in sizes 5–13 and five colors).
Psst: This item is included in Prime Try Before You Buy, so you can give it a trial run if you're a member!
2. A Sorel wedge bootie that'll give you all the style of a heel with all the function of a boot, making it the ideal shoe for the quickly approaching fall season.
BTW, it's made with waterproof leather so you can even step on wet leaves!
Promising review: "I have been wanting these Sorel Wedge boots forever. A gift card solved that problem so I purchased these beauties. Just got them today and I'm in love. They are sleek and minimal with the side zipper, which adds just the right touch of chic. And they are amazingly comfortable. I don't wear 3" anything but you would never know these are 3" with the wedge heel. They make your legs look a mile long. And I swear they make my butt look good. Now, I'm likely delusional, but at age 59, I'll wear anything that makes my legs and my butt look good. I'm gonna wear these babies around the house naked they’re that good. I live in Denver so they'll be ample opportunity to wear them in the snow and everything I've read says they're great for that. I'm calling this pair my best booty boot. Buy them. You'll see." —Joangee
Get them from Amazon for $95+ (available in sizes 5–12 and 13 colors).
3. Calf-friendly boots for the peeps who have always struggled with finding the perfect pair of below knee-high boots to fit around their wide *or* narrow calves.
I got a pair of these for my sister-in-law who every year complained about never being able to find boots that fit her wider calves. She did the Find Your Fit test to figure out which size would be the best fit for her, chose a pair, and is absolutely obsessed. She gushes about how comfortable and stylish they are and is so ecstatic to finally have a pair she can zip all the way up!
Get them from DuoBoots for $237 (available in sizes 5–12 and eight calf widths).
4. A pair of Dansko clogs that you may think are clunky and weird, but I promise you, they'll look absolutely adorable on you!
These clogs have a dual density EVA footbed with memory foam for cushioning and support!
Promising review: "I broke my foot 37 years ago, and it left me with a bump/deformed foot, so I can only wear Mary Jane type shoes. These are so comfortable, so stylish, and so quiet for clog-type shoes! I have tried other more expensive clog-type nursing shoes, and they do not come close to the comfort of Dansko shoes! I love them!!!" —Kate
Get them from Amazon for $139.95+ (available in sizes 5.5–12 and two colors)
5. Classic Bean boots for all types of messy weather *and* for that New England chic vibe. Rain, snow, and mud-approved!
6. A snazzy vegan loafer that'll pair with every single outfit you own in your closet. They're timeless! They're chic! They're even ethically sourced!
7. Classic Birkenstocks because you've seen people wear these for years and trust me, there is a reason they're popular. Do it. You know you want to.
Made with 100% suede!
Promising review: "Fits like a dream. I'm in love! This is my second pair of Birkenstocks. I'm used to open-toe style sandals, but these are way more comfortable! I thought I would have to break them in, but they were so comfortable right out of the gate due to the suede top and the soft foot bed. Trust me they're AMAZING!" —LorenaMae
Get them from Amazon for $89.95+ (available in women's sizes 5–13.5, men's sizes 5–9.5, and 25 colors).
8. Everlane flats designed to mold so well to your feet that you may actually forget you're even wearing shoes.
9. Steve Madden ankle boots that effortlessly combines style, comfort, and function for the absolute *perfect* shoe this upcoming winter season.
10. A pair of Sorel strappy sandals to basically become your designated important errand shoes. By important errands, I mean your third trip to Target for the week. They also come in some really funky colors!
Promising review: "Just perfect! I love these! They're so comfortable. I can walk a mile and more in these." —Carolyn O.
Get them from Amazon for $71.40+ (available in sizes 6–12 and seven colors).
11. Pointed-toe heels with a bow tie and cutouts along the ankles that'll look gorgeous year-round but especially when you layer it with your date night fall outfits.
Promising review: "Absolutely gorgeous! These are comfortable as well. I wear a size 9 but ordered a size 8 due to other reviews regarding sizing and they fit perfectly. I wore these to a holiday party and received so many compliments." —Teresa
Get them from Amazon for $44.98+ (available in sizes 5.5–11 and 20 colors).
Psst: This item is included in Prime Try Before You Buy, so you can give it a trial run if you're a member!
12. A timeless pair of slip-on heels for when you just don't want to commit to wearing a *high* heel at the holiday party you're invited to but still want to dress the part.
I got these in red and they're my go-to heels when I want my outfits to look a bit dressed up, but I don't want to commit to wearing actual pumps. They're SO comfortable and look absolutely adorable on. I will say, they're VERY squeaky at first because of the leather, so that's a little bit annoying. However, it goes away once they break in and it's not an issue! It was kind of funny walking around and sounding like an old-timey villain in a cartoon. They're definitely a splurge, but absolutely worth it as I know these will be in my collection for many, many years to come!
Ma'am is a woman-owned small business based in Los Angeles, California dedicated to providing high-quality, yet stylish footwear for everyone.
Promising review: "I adore these heels! First off, they look great with a casual dress, shorts, and even jeans. Beyond that, they’re amazingly comfortable from the first wear. I would definitely recommend this high quality product." —Molly Swanson
Get them from Ma'am for $300 (available in sizes 4.5–11 and five colors).
13. Dr. Martens combat boots so you can finally jump on this bandwagon that is definitely here to stay. They're wicked reliable, so you can wear them through rain, sleet, and even snow!
14. Or Sam Edelman combat boots, for when you like the Doc Marten look, but the neutral colors of these just suck you right in.
15. Hunter boots that will not only keep your feet dry from rain puddles (and hey, even snow!), but they just look so great over jeans or leggings.
16. A Rebecca Allen pump to get you through the workdays looking totally put together, even if you don't feel it.
Rebecca Allen is a Black woman-owned small business that sells stunning, classic shoes for your everyday person.
With its all leather construction, this pump is *made* to be worn for many years to come. It's so timeless and classic, it'll never go out of style. Basically, it's a splurge up front, but you'll get your money's worth with every step you take.
Get them from Rebecca Allen for $185 (available in sizes 6–11).
17. Western-style boots that'll have you "yeehaw-ing" all over your house feeling like Miley Cyrus circa 2010.
Promising review: "You will love these boots!! They are absolutely gorgeous! I wore them straight out of the box to the state fair. My feet were comfortable the whole time except the last hour. I was walking around for four hours! Buy these boots!!!" —Fashionprincess
Get them from Free People for $328 (available in sizes 6–11 and 11 colors).
18. Asics running shoes because what better way to get your money's worth with your shoes than to run ~miles~ in them.
The multi-directional mesh material improves ventilation and stability while the GEL technology cushioning provides excellent shock absorption.
Promising review: "I like the comfort and the fit of these shoes. I have been using Asics for several year, and they keep me coming back. Very good quality and comfort. Although they are high priced, in my opinion, the quality is worth the investment. The sizing was spot-on with the measurements I received from a shoe store. Sizing has been consistent style to style." —Jerri
Get them from Amazon for $84.95+ (available in sizes 5–12.5, wide sizes, and 18 colors).
19. A pair of vegan sneakers that are made with a surprisingly light and flexible formula designed to deliver optimal comfort and style for all your errands, commuting, and overall fabulousness.
So I have these shoes, and they're truly one of my new favorites. They're incredibly lightweight and comfortable and the color is so chic and timeless They go with all of my winter looks and I feel like I could wear them all day every day and not get sore feet!
Cari Capri is a woman-owned small business specializing in stylish eco-friendly apparel and accessories.
Get them from Cari Capri for $150 (available in sizes 6–11).
20. A cut-out mule elegantly designed to be a more sophisticated version of a flat you can slide on without having to deal with straps or buckles *and* not look too childish like some ballet flats do.
Zou Xou Shoes is a Black- woman-owned business that has been creating handcrafted shoes by Argentinian shoemakers since 2015. The styles are easy and classic so they can be worn for years. These mules are handmade to order in European sizes, and they suggest sizing up. So, if you wear a US 8, choose a 39.
Promising review: "OMG they are perfect!!! As soon as I opened the box I could smell the quality. I’ve been eyeing these shoes for months and they are so worth it! Keeping these forever. ❤️ So happy to support!" —Isabella Henriquez
Get them from Zou Xou Shoes on Etsy for $249 (available in European sizes 36–42) or from Zou Xou Shoes for $245 (available in European sizes 35–43).
21. A pair of sleek Chelsea boots that'll quickly become your go-to shoe for every single outing *and* for many years. One of those outings might just be secretly walking around the house in them. Just once. 👀
They've got memory foam, five-layer, cushioned insoles!
Nisolo is a small business that sells ethically created, sustainable footwear.
Promising review: "Beautiful boots and comfortable right out of the box. They fit true to size. Like most of my Nisolo boots, I wore them around the house with thick socks for a couple of hours to get them a little softer. This pair was so comfortable that I quickly forgot I was wearing new boots! I like the casual look of the lighter grained sole of these and the rubber anti-skid sole will be great in the winter months. They are perfect casual boot. I’m a huge fan of Nisolo shoes for look, quality, and sustainability practices and they’ve once again impressed me with these." —Julie J.
Get them from Nisolo for $200 (available in sizes 5–11 and six colors).
22. Or a Chelsea boot to save you a *wee* bit of money, because they're not just a wardrobe staple, but a wardrobe *must-have*.
100% genuine leather!
Thursday Boot Company is a small business specializing in created high quality footwear that'll not only stand the test of time, but will look fabulous while doing it.
Promising review: "Everyone — EVERYONE — at the place I work wears some type of Chelsea boot, ranging from the flashy to the more functional. I wanted something that was both sleek and professional as well as sturdy for walking 40 min in the rain every day, and these shoes fit the bill perfectly! Time will tell, but so far they seem to be waterproof as well as slip-resistant. I normally wear a 7–7.5 and sized up to an 8. It's roomy enough for thick socks, but close fitting enough without. No ankle chafing either! I'm very pleased with these shoes!!" —Danielle
"These are the most comfortable boots I've ever owned, and I've owned a LOT of boots. I just bought my second pair because my old ones are starting to show wear after 18 months of hard use, and now I'll have a pair for getting dirty and a pair for town. They take a little breaking in (I can tell, because my old ones are way softer than my new ones), but that just means they're quality leather." —Lori
Get them from Amazon for $160 (available in sizes 5–11 and eight colors).
23. Ultra-chic low-top sneakers that'll effortlessly make even your most casual of outfits look like you're a fashion influencer dressed for a #chillday.
I had been on the hunt for a stylish pair of black sneakers like this for a really long time, but I could never find the good balance between a shoe for fashion and function...until I found these bad boys. They're exactly what I was looking for, which was to have a pair of kicks I could wear to make an outfit look more casual, but at the same time still look super put together! I love pairing them with leggings and hoodies the most! They're super comfortable and flexible, so it felt like I didn't have to break them in at all.
Get them from Thursday for $129 (available in sizes 5–12 and eight colors).
24. Lace-up booties perfect for when you want to keep your feet toasty warm, but don't want to commit to longer boots.
Promising review: "These boots are made so well! They are unbelievably comfortable; there is no need to break them in. The first day wearing them I stood for several hours and had no trouble at all. These are by far my favorite boots. I will be getting more in the future." —Lisakay
Get them from Amazon for $130+ (available in sizes 5–11 and seven colors).
25. Columbia hiking boots that are waterproof, lightweight, *and* have advanced traction rubber soles to handle any kind of terrain you put in their path.
Before I got these shoes, I used to have a pair of Merrell's that I found were just way too awkward and clunky for me to walk in. I finally bit the bullet and bought these Columbia boots, and it was the best decision I have made! They're incredibly comfortable and provide so much support around my ankles. I love that they're waterproof, so I don't have to tread lightly through mud or water — I just stomp right through! I've worn them in short four-mile hikes and long 14-mile hikes, and they've been equally comfortable in both!
Promising review: "I needed a waterproof boot that would also be good for lots of walking. I did a lot of walking in Ireland and Scotland, mostly in rainy weather, and these boots were true to their description. My feet were dry and comfortable." —Louise M.
Get them from Amazon for $59.02+ (available in sizes 5–12, wide sizes, and 14 colors).
Psst: This item is included in Prime Try Before You Buy, so you can give it a trial run if you're a member!
26. Kitten heels you can wear to work *and* for a night out with the besties without having to change your outfit.
The metallic lining detail is the perfect touch, isn't it?
Promising review: "I bought these shoes in both lavender and mint- no regrets. They’re really sexy, comfortable to walk in, and remind me of '90s glam in the best way. They’re the perfect shoe to dress up or down. Highly recommend! Thinking about getting the nude as well." —Lauramc2
Get them from Free People for $138 (available in women's sizes 6–11 and 12 colors).