Unless otherwise specified, all sizes in this post are listed in women's.
1. A pair of super-sturdy, high-quality Chelsea boots everyone should own a pair of. You'll instantly realize how smart of a purchase you made when you discover these can go with literally any outfit you pick out this fall.
Promising review: "After a lot of worry about getting the right fit, I took the advice given by the reviewers and the company and ordered a half size larger. They fit great! The leather is beautiful. They smell really good. They look very suave and debonair. I’m sitting on the sofa watching TV because I don’t want to take them off. I debated a long time and worried a lot about buying these boots because of some of the negative reviews, but I’m glad I went with the majority of reviews. They were not too narrow and fit comfortably. They also were not too long. They are the look that I was going for. A dressier look than my normal work boots that I bum around in. I’m very happy with these classy boots!!" —CMaxDavis
Get them from Amazon for $160 (available in sizes 5–11 and in eight colors).
2. Or these waterproof Chelsea boots if you don't love the clunky design of a traditional rain boot but still want protection against rainy conditions this fall — but in a fashionable way of course. Now you don't have to rework your whole outfit just because it might sprinkle later!
Promising review: "I go to school in Santa Cruz and it rains a lot over here so I thought I should invest in some stylish rain boots. These are perfect because they aren't too clunky and obnoxious but they are able to keep warmth in and rain out. I also love how trendy they are because I don't feel like I'm wearing two traffic cones on my feet." —Tara Mashkory
Get them from Amazon for $26.95+ (available in sizes 5–11 and in 11 colors).
Psst: this item is included in Prime Wardrobe so you can give it a trial run if you're a member!
3. A pair of waterproof Columbia hiking boots so you can embrace your outdoorsy side this fall and go on some nature hikes to get an up-close view of all those changing leaves.
I've owned these hiking boots for the past three years and I absolutely love them! When I bought them, I was looking for something with ankle support because I have really weak ankles and was sick of rolling them whenever I misstepped while hiking. They do a great job at keeping my feet protected and supported during hikes, and I love that I don't have to worry about it raining or being soggy on the trail thanks to the waterproofness. Lastly, I love that they're not too heavy or bulky — if you're already climbing up a mountain, the last thing you need is extra weight on your feet!
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 $75+ (available in sizes 5–12, two widths, and eight colors).
Psst: this item is included in Prime Wardrobe so you can give it a trial run if you're a member!
4. A pair of classic riding boots — this investmentworthy piece is such a timeless style, you'll feel justified spending a bit more on them. After all, they'll be in your wardrobe for years (even decades!) to come.
Get them from Anthropologie for $230 (available in European sizes 36–41, 36W–41W, and in two colors).
5. Or these riding boots with a lace-up feature that takes this classic design to a whole new level. Whether you wear these with your jeans tucked in or over leggings, you'll love showing these off with all your new fall sweaters and dresses.
Promising review: "I love these! I get lots of compliments on them. They're super comfy. I would say they are not quite a half size larger. I got the 9, which is usually pretty well fitted on me. These are loose enough that I can wear very heavy socks comfortably. If you are on the fence, I suggest getting them. You will be happy you did." —Erin M. Metz
Get them from Amazon for $24.99+ (available in whole sizes 6–11 and in three colors).
6. A pair of chunky boots with two super-trendy design details — a sturdy lug sole and a sock-like design going up the ankle. If your main objective this fall is to actually stick with the trends, this is the boot for you.
Promising review: "They're very cute and high quality! The only thing is they are a little snug to slip on and off, but they are extremely comfortable. They are wide set, which is perfect to wear thicker socks with. And the bottom has stars! I want them in every color." —Angie
Get them from Amazon for $69.98+ (available in sizes 5–11 and in 20 colors and styles).
Psst: this item is included in Prime Wardrobe so you can give it a trial run if you're a member!
7. *Clog booties that transform the clog trend that was alll the rage this summer into a cold weather-appropriate look. Not only does the clog base give you a little lift, but the fleece lining will keep your toes nice and warm on those chilly days!
It also has a memory foam insole!
Promising review: "These boots are so cute. Very Scandinavian cool and comfortable. I think they could work with most outfits and look much more expensive than they are. I have medium to wide feet and they fit well." —BohoBrit
Get it from Target for $39.99 (available in sizes 5–12 and two colors).
8. Classic waterproof duck boots — they're practically screaming at me to wear them any time I head outside this fall.
Promising review: "I am thrilled with these boots! I took a chance on them and went to Seattle in the winter hoping they would keep my feet dry and comfy. They did not disappoint! We hiked, walked on beaches, it rained, and it snowed, and I wore these boots every day and my feet were always warm and dry, and they held up perfectly. Not to mention they looked great! :) They made this pregnant lady very happy and I highly recommend them." —L.McDaniel
Get them from Amazon for $45.99+ (available in sizes 6–11 and in 12 colors).
9. Knit and faux-fur-lined booties to keep your toes extra warm on those chilly fall nights full of bonfires, hayrides, and jumping into leaf piles.
Promising review: "Nothing but good things to say about these boots. Absolutely love them! I have big feet (size 10) and was concerned these boots would make my feet look huge. Not the case at all! I love them and they’re my new favorite pair of shoes. They’re a tiny bit tight with thick socks on, but I’m sure they’ll stretch a little with time like all shoes. These boots look cute with some leggings and thick socks, and by themselves with some skinny jeans. 10/10 would definitely recommend!" —jackie kessler
Get them from Amazon for $35.19+ (available in sizes 5.5–10 and five colors).
10. Microsuede ankle booties so versatile, you're bound to wear these at least three times a week. Pair them with straight leg jeans, your favorite skirt, or even tights and a cute fall dress.
Promising review: "Yesss. I was looking to replace a far more expensive pair of boots (I wear a size 12). I'm so surprised at the look and fit of these shoes. Nailed it, Amazon!" —Allison Buck
Get them from Amazon for $39.40+ (available in sizes 5–15, wide sizes, and in five colors).
Psst: this item is included in Prime Wardrobe so you can give it a trial run if you're a member!
11. A stiletto bootie with a super-glamorous cutout on the side that's lined with beautiful rhinestones. Is this footwear or a piece of art? I think it's both.
Aminah Abdul Jillil is a Black-owned, woman-owned small business based in Los Angeles that designs bold, fashion-forward luxury shoes.
Get it from Aminah Abdul Jillil for $578 (available in sizes 6–11).
12. Classic Dr. Martens combat boots that are so worthy of the investment because once you break them in, you'll be rocking these for literal decades to come.
13. Kitten heel booties to instantly glam up any outfit you wear them with. Seriously — you might just be wearing a simple T-shirt and jeans, but then you put these on and BAM: Instaworthy ensemble.
Promising review: These are the booties I've been looking for. They fit perfectly. I wear a size 5.5 or 6. I got the size 6 because I already tried on the 5.5 and those were a little snug. The size 6 is perfect. I wore them to dinner and they are really comfortable to walk in. I just ordered the burgundy ones." —Kathleen Garner
Get them from Amazon for $22.71+ (available in sizes 5–11 and six colors).
Psst: this item is included in Prime Wardrobe so you can give it a trial run if you're a member!
14. Some bold '70s-style booties if you're looking to channel your inner dancing queen, even if you're just strutting down the street heading to your local coffee shop. These are a seriously show-stopping pair of shoes that everyone will be complimenting you on!
15. A stylish glove boot from Everlane that feel like you're just wearing your coziest socks instead of actual footwear. You'll be hard-pressed to find a more comfortable look on this list!
Promising review: "At first, I wasn’t completely sold on the bootie. I had eyed it for a while and then decided to go for it. What a wonderful decision that was! They are extremely comfortable and hug your feet as you stand and walk. The heel height is perfect for being on your feet many hours a day. The knit is soft and stretchy and made for true comfort. I would give these boots a 10-star rating if I could. Go ahead, treat yourself...your feet will be so happy you did!" —ShoeLover4Ever
Get it from Everlane for $130 (available in sizes 5–11 and three colors).
16. This thigh-high option with some toe cutouts — if you just got a pedicure and want to show off those freshly painted toes, go for it!
Lilly's Kloset is a Black-owned, woman-owned small business based in Houston, Texas. The founder Kemetria Lilly is committed to creating affordable and accessible fashion.
Promising review: "I love these heels!!!!! OMG the quality is AMAZING!! The toe area fits fine and has some stretch. I have thick thighs so these fit like a dream!! They also arrived on time and were not damaged. Will be buying from again." —Ruth R.
Get it from Lilly's Kloset for $78 (available in sizes 5.5–11).
17. Chunky-heel booties that come in a variety of different colors, but we're partial to the white ones because they'll help you stand out in a sea full of black, brown, and beige boots this fall.
Promising review: "Chic at a low cost. I was iffy because the price point was so low, I was scared they'd be costumey. But these boots are a killer mod and chic addition to my wardrobe. Fall in California. Arrived without a scratch, double wrapped in tissue paper with a branded box. They have a zipper on the outside for decoration and a true zipper on the inside to get on and off. UPDATE: I've worn them out three times now (twice for grocery runs and once to work) they are very comfortable but are losing their shape a bit. Not necessarily a bad thing (I'm not docking any stars) since I'm interested to see how this faux leather will wear in." —Sasha McKinley-Yunker
Get them from Amazon for $43.99+ (available in sizes 5.5–11 and 12 colors).
18. A pair of black platform booties you'll be stomping around in all autumn long. Just imagine how satisfying it'll be crunching leaves with these bad boys!
Promising review: "I bought these black platform boots for the added height to wear with my dress pants so I didn't have to hem. They are perfect! They are so comfortable, so I can wear them for nine hours straight at work! With the thick heel, I can take the stairs up and down and not have any worries like I do when I wear skinny heels. They even look cute with jeans." —Tricia Thomas
Get them from Amazon for $29.99+ (available in sizes 5.5–10).
19. Waterproof mid-calf snow boots that look way more chic and fashion forward than your normal snow boots. And you don't have to wait for the first blizzard to start wearing these — they make a great fall boot, especially when it's raining and cold outside!
Promising review: "I just received these boots and tried them just around the house. Super comfy and light, very warm. They have a thick fur lining inside to keep my feet warm. They look waterproof, though I haven't tested them yet. My favorite part is the zipper!! The laces make the boots adjustable to fit snug or loose to your calf. So different types of pants can fit in them. I am ready for the snow!" —Amazon Customer
Get them from Amazon for $59.99+ (available in sizes 5–12 and in 18 colors).
Psst: this item is included in Prime Wardrobe so you can give it a trial run if you're a member!
20. Fluffy shearling-and-suede lace-up Ugg Neumel boots if you're missing the comfort of those classic Ugg boots you wore in middle school but want something that's a bit more fitting for this decade.
Promising review: "I have always been a huge Ugg fan, but these boots are my absolute favorite! They are super warm and comfy and just like regular Ugg boots they are roomy, so you can round down a half size." —HuskyNurse
Get them from Nordstrom for $99.99+ (available in sizes 5–12 and in five colors).
21. Glittery heeled booties because you'll love showing that shine whenever you enter the room. Everyone needs a little sparkle in their shoe collection!
Promising review: “I have wide feet, and these felt comfortable to wear. They are SO PRETTY!!! Even prettier in person! The glimmer is amazing, and I am obsessed with them. They are taller than they look, but I wore these out for a night on the town and was able to wear them the whole night out as we restaurant hopped (about four hours). Highly recommend these!" —Amazon Customer
Get them from Amazon for $46.99+ (available in sizes 5.5–10 and nine colors).
22. Some scrunched cowboy-style boots — your fall wardrobe is practically begging you to add some Western flair to it this year!
Get it from Anthropologie for $180 (available in European sizes 36–41 and two colors).
23. Or these white pointed-toe booties — this cowgirl chic style will give you confidence as you're rocking your favorite outfit this autumn.
24. Some low-wedge booties if you're looking to give yourself a bit of a lift this fall but want to try something else besides a chunky bootie.
Promising review: "These are a surprisingly great alternative to more expensive brands in the same style. They are very comfortable, which is saying a lot because I often have terrible foot and ankle pain. I highly recommend these wedges." —M. K. Miller
Get them from Amazon for $31.99+ (available in sizes 5–12 and in 11 colors).
25. A pair of platform boots with three buckles that give a rocker edge to an otherwise classic pair of shoes. These tough-looking shoes have a secret — they're actually super comfortable and have a fleece lining for extra warmth!
Die With Your Boots On is a small business based in Salem, Massachusetts, (spooky!) that sells Halloween-inspired dresses, tops, shoes, and more.
Get it from Die With Your Boots On for $50 (available in sizes 4.5–12.5).
26. An ankle boot with a fun side cutout and a ruffle detail if you're looking for some boots that add a bit of flair to your wardrobe. They also can be worn in the summer thanks to the breeziness of the design!
Promising review: "I bought these in several colors and love every pair. They are super cute and comfy. I love the ruffle — it gives them a fancy feel. I want them in every color now!" —Jordan Pemble
Get them from Amazon for $53.98+ (available in sizes 5.5–11 and in 11 colors).
27. A pointed-toe heeled bootie polished enough to wear to work while still being cute enough to wear to happy hour with friends. Bonus: they come in a fun silver metallic color if you're looking to go more bold!
Promising review: "I purchased this boot in silver. It is very comfortable and easy to pair with a variety of outfits. These will be my go-to pair of the season!" —babybluexsedan
Get it from Target for $37.99 (available in sizes 5–11 and two colors).
28. These retro leather boots that give the classic riding boot a mod-style upgrade with the white detailing, the square toe, and the block heel. Pair this with a plaid mini skirt and a black turtleneck for an instantly chic ensemble.
Alohas is a small, woman-owned sustainable shoemaking company that uses an on-demand production system, which means they create their products based on the number of orders they receive. They make awesome (and non-wasteful) boots, sneakers, loafers, sandals, and more!
Get them from Alohas for $363 (available in EU sizes 35–42 and two colors; consult their size chart to find your US size).