Unless otherwise specified, all sizes in this post are listed in women's.

1. A pointed-toe flat, because working on your feet requires a comfy shoe — but that doesn't mean it can't look cute, too. This'll provide cushion on your feet while adding a sleek, elevated vibe to your outfits!

Zappos

Promising review: "As soon as I tried these on, I went back online to see if they came in other colors. I've never worn ballet flats that ACTUALLY HAVE ARCH SUPPORT!! Love it" —Anonymous

Price: $91.95+ (originally $120+; available in sizes 5–12, narrow, medium, and wide fits, and styles)

2. A zip-up ankle bootie with just a bit of a heel to keep you trekking all day long. You can wear this with anything from your go-to jeans to a flouncy fall dress.

Zappos

Promising reviews: "I really like these boots. The upper portion is soft leather. The shape of the boot is sleek and not clunky. They are comfortable and look great!" —Anonymous

"A perfect fit for me. This is my third pair of these booties...nice height...goes with everything." —Anonymous

Price: $77.40+ (originally $129+; available in sizes 5–11, medium and wide fits, and five colors)

3. A pair of Sorel waterproof sneakers if you're not so much of a rain boot person. These also have a really cushy platform for extra support!

Zappos

Promising review: "WOW. I created a Zappos account just to be able to write this review. These shoes are THE BEST. I ordered them a few days before my vacation after I found out it was supposed to rain the entire time. (Shout out to Zappos for getting them to me in time!) They were so comfortable and kept my feet dry. One night, we got caught in a torrential downpour and ran through several puddles. My pants were completely soaked through, but these shoes kept my feet completely dry!!!! I wore them almost every day for two weeks and walked over 15k steps a day without blisters or pain. I’m in awe. If you’re looking for a great waterproof shoe, these are it." —Anonymous

Price: $57+ (originally $94.95+; available in sizes 5–12 and in four colors)

4. A buckled Mary Jane, because Wicked 2 is premiering soon. Sure, these may not be sparkly red shoes, but you can still wear them to the theaters for a Dorothy-leaning look.

Zappos

Price: $99.95 (available in sizes 5.5–11)

5. A Mary Jane pump with a cute metallic trim to elevate your current go-to black pumps.

Zappos

Price: $155 (available in sizes 5–11)

6. A riding boot so that you can emulate your inner horse girl, even if you don't plan on hopping onto a saddle this season. These, plus a midi dress, are everything for the fall season.

Zappos

Promising review: "They were a bit snug at first, but I wore them with thicker socks around the house to stretch them out a bit. Now they are just perfect and are so comfortable." —Anonymous

Price: $298 (available in sizes 6–11)

7. A Coach platform loafer to give you both a little lift and a little prep in one easy-to-slip-on shoe.

Zappos

Promising review: "I love these shoes!!! They are so cute and comfortable. It fits true to size, and I can't wait for the brown or black to go on sale because I will buy them, too. They are a MUST-have!" —Cheryl

Price: $135.07+ (originally $195; available in sizes 5–11 and three colors) 

8. A Crocs platform mule that brings the classic Croc into the fall and winter seasons! These have a closed-toe design for extra coverage in cooler temps, but still have that beloved spongey Croc feel.

Zappos

Price: $64.99 (available in sizes 5–11 and two colors)

9. A pointed-toe slingback since leopard is basically the pattern of the season. Hop on the trend with what'll be your new office shoe.

Zappos

Promising review: "At first, I didn't have much faith in these as I had already tried on many pairs of pointy-toed kitten heels, but they are amazing! The fit is great. I think it's because they're longer in the toe box than the others I tried, so when my foot slides forward, my toes aren't being pushed into a tiny point. The heel is comfortable, and the cushioning is just right. It's an updated classic look that I will wear for years to come." —Anonymous

Price: $74.99+ (originally $140+; available in sizes 5–13, medium and wide fits, and 20 colors/materials)

10. A pair of Hoka sneakers that are perfect if you're training for a 5K. I have blown through about three pairs of Hokas at this point, and their cushioning is perfect for long runs and workouts.

Zappos

Promising review: "The fit is excellent! I've had a hard time finding shoes in my size in wide. These have plenty of room and don't make my feet feel cramped. There is enough cushioning to feel supportive but not overwhelming. My feet feel great in these!" —Anonymous

Price: $140 (available in sizes 5–11, medium and wide widths, and 20 colors) 

11. A lace-up ankle bootie to bring your outdoor gear to everyday life. If you find that you often wear your hiking boots on rainy or snowy days, you can swap them out for these shoes — while they look like everyday booties, they have the same waterproofing (hi, a Scotchgard-treated upper!) and tread as your more durable footwear.

Zappos

Promising review: "These are amazing! I think I squealed when I opened the box. They are beautiful. I know I sighed when I put them on. Propet understands what VERY wide feet are like. They also understand that even women with Flintstone feet want stylish, comfortable footwear. And they deliver. I plan to buy more of these. And speaking of delivery... I received these shoes 30 minutes before I got a shipping notification. They got here FAST. This is my first Zappos order (though not my first Propet purchase), and I couldn't be happier. Great prices, great brands, great styles, and, at least for this order, free shipping that was faster than a timely email! Any company offering such great products and service has a customer for life in me." —MommaSuz

Price: $97.74+ (originally $109.99+; available in sizes 6–11, narrow, medium, wide, X-wide, and XX-wide fits, and six colors)

12. A Sam Edelman ballet flat, because flats are so back! Since these have a scrunched design, you can easily slot them into your bag whenever you need to give your feet a break from heels (I'm looking at you, wedding guests).

Zappos

Promising review: "You know someone loves a shoe when they buy a second pair of them...and I just ordered my second pair. I got a pair this spring, just before I had some minor foot surgery. It turned out to be one of two pairs of shoes I could wear without pain because it doesn't have any pressure points. I literally wore these for three weeks straight. I love this shoe because I can wear it with jeans or skirts, and it's easy to wear on a plane. They pack great!" —Ann

Price: $54.75+ (available in sizes 6–11, narrow, medium, and wide fits, and eight colors)

13. A square-toe slingback pump so that you can enjoy the look of a heel with the support of an adjustable strap.

Zappos

Promising reviews: "Fit was true to size and very comfortable. Very attractive shoe, especially for a larger foot." —Lisa

"Material is soft. Super comfortable shoe, stylish, and perfect width." —Anonymous

Price: $90+ (originally $125+; available in sizes 5–12, in narrow, medium, wide, and X-wide fits, and nine colors)

14. A chic suede boot since suede is back, y'all! These'll look great paired with an oversize blazer and chunky vintage jewelry.

Zappos

Price: $275 (available in sizes 5–11 and two colors)

15. A Keds white lace-up sneaker if you love the look of a white sneaker but want something more durable than a canvas shoe. These have the same comfort and design as classic Keds but with a leather upper!

Zappos

Promising review: "After trying at least 20 white sneakers, this one is a hit. The leather is soooo comfortable as compared to canvas. The style is just what I was looking for: not too athletic and not too casual. Buy them. You won’t be disappointed" —Carol

Price: $64.95 (available in sizes 5–11)

16. A vegan suede slip-on mule, because they're an easy shoe to wear both in and out of the house! Wear these with wide-legged jeans when you're off to a coffee shop, or pair them with your favorite yoga pants as you do some housework.

Zappos

Price: $69.95 (available in sizes 6–10)

17. A Madewell Laurel bootie so that you can look chic as heck as you commute to the office. These work just as well with a midi skirt as they do with your favorite barrel jeans.

Zappos

Price: $228 (available in sizes 5–10.5)

18. A bow slingback flat to help you bring a coquettish vibe to your otherwise neutral-leaning fall wardrobe.

Zappos

Price: $140 (available in sizes 5–13)

19. A tall Steve Madden cowboy boot, because cowboy boots are a classic comfort shoe (cowboys wear them for a reason!). These come in cute colors that are muted enough to go with most of the pieces in your closet, but still bold enough for a cool twist on your footwear.

Zappos

Promising reviews: "The other reviews made me worry these would be too narrow, but they are so cute I ordered them anyway in my regular size, and I was not disappointed. My feet are fairly wide across the toes, and while I would describe these as snug, they are completely comfortable. I wore them for 10 hours today, and my feet didn't hurt at all, and I got a ton of compliments from everyone. I did wear them with tights, though. If I wanted to wear them with thick socks, I'd have to go up a size. I'm always wary of brown leather, too, because if the color's not just right, it can look really cheap, but these look expensive, and the leather is very soft, supple, and smooth. These might be my new favorite pair of shoes!" —Cecily

"I have been looking for the perfect riding boots for ages, and I am thrilled to have found them! The zipper works, making it easy to get in and out of these boots, and the leather is lovely. I bought the chocolate color, and they are very pretty. They are super comfortable right out of the box! I have slightly wide feet, and these fit just fine. I have fairly big calves, and these have just enough room to wear tights. There is a vent that allows for even more room, but I am not sure that I will push it with much more than leggings for now." —Anonymous

Price: $86.38+ (originally $179.95; available in sizes 6–10 and four colors)

20. A sophisticated pointed-toe heel to add pizzazz to your all-black wardrobe! The mesh ankle strap also makes it really easy to slip these shoes on and off!

Zappos

Promising reviews: "Bought these for a trip to NYC. They were everything I wanted and more. I had to actually run to catch a cab ten minutes after I first put them on, and forgot they were even on my feet! Comfortable immediately and longer! So happy." —Ellen

Price: $47.99 (originally $79.99; available in sizes 6–11, medium and wide fits, and in two materials)

21. A heeled penny loafer, because they'll go with every last work outfit you have planned for the fall. These have a short block heel to provide just the right amount of lift that won't ache throughout the day.

Zappos

Price: $95 (available in sizes 5–11 and medium and wide sizes)

22. A pair of New Balance 327 sneakers that you'll love to slip into for early morning jogs, errands, or simply strolling around the city.

Zappos

Promising review: "Best sneakers I’ve bought in a long time! So cute and comfy and versatile" —Anonymous

Price: $74.99+ (available in sizes 5–12 and 17 colors)

23. A heeled bootie you'll reach for every single weekend! They'll quickly become your go-to going-out shoe, whether you're off to dinner or are bar-hopping with your pals.

Zappos

Price: $119 (available in sizes 6–10 and two colors)

24. A pair of Blundstone Chelsea boots, because they're rugged enough for long treks, but cute enough to wear every day! These are also a favorite amongst restaurant workers for their closed-toed design and comfy feel.

Zappos

Promising review: "These boots are worth every penny! After a short period of breaking in, they feel great for hours of walking on trails or even in town. They keep your feet warm and dry." —Anonymous

Price: $209.95 (available in women's sizes 6–16 and men's sizes 4–14)

25. A pair of Ugg slippers so that you can elevate your indoor footwear, too! These are comfy as heck and will keep your toesies warm during the cooler months.

Zappos

Promising review: "This is my second pair of Ugg slippers. I love them. They felt a little snug when I first put them on, but within a few hours, they were perfect. My last pair lasted two years, and I wear them every day, all year long. I wear a 7.5 and got an 8, they fit perfectly." —Anonymous

Price: $99.95 (available in sizes 5–12 and six colors)

26. A checkerboard Vans slip-on shoe that is a classic shoe for a reason! These have elastic straps that help the shoe conform to your foot, becoming comfier over time.

Zappos

Promising review: "LOVE! These are my eighth pair of Vans and they're so stylish. I especially love the slip-on style because they are so convenient." —Kayla

Price: $60+ (available in women's sizes 5–17.5, men's sizes 3.4–17, and 16 colors)

27. And a square-toe Mary Jane, because there's something inherently preppy about fall, and there's definitely something super preppy about Mary Janes. Pair these with white socks and a plaid dress for the ultimate back-to-school look (even if you've been graduated for years).

Zappos

Price: $150 (available in sizes 6–11 and two colors)

Reviews have been edited for length and/or clarity.