Unless otherwise specified, all sizes in this post are listed in women's.
1. A flowy tiered shift dress to achieve max comfy-cuteness whether you're bridal shower bound or just headed out on a fall foliage stroll.
If you're blessed in the boob department, reviewers recommend ordering a size up because of a seam that sits right below the bust.
Promising review: "I can’t say enough good things about this dress. The length is great, and the fit is great! I probably could have done a small but didn’t want it to be too short for work. Perfect dress to dress up with wedges or heels or dress down with booties or sandals." —Kayla
Get it from Amazon for $32.97 (available in sizes S–XXL and in 41 styles including short sleeve).
2. A beloved Carhartt beanie so you can join the legions of people who already love this rib-knit cap. It comes in loads of different colors, so you never have to compromise your style for head warmth.
3. Iconic Dr. Martens Chelsea boots with slip-resistant soles that add an instant cool factor to any look, and a bit of height, too. The versatile staple is shockingly comfortable and durable enough for all of fall's most unpredictable weather.
FYI, this is included in Prime Try Before You Buy so you can give them a trial run if you're a member! ALSO, many reviewers say these run big, so consider sizing down!
Promising review: "I have been wearing Docs for years now, and this pair has to take first place for comfort. They're incredibly cute and versatile, can be dressed up or down, and just like any other pair of Docs are faithfully durable. Docs always run big so I sized a full size down and still comfortably wear them with thin–thick socks. I brought them on a long trip, wore them in various weather conditions like rain/snow/forest trails, and they worked great." —Stacy Cruz
Get it from Amazon for $60+ (available in sizes 5–11).
4. A pair of high-waisted faux leather leggings for anyone who's been eyeing another (more expensive) pair of internet-famous pleather leggings for a while. This is a cheaper alternative that achieves the same great look.
FYI, this is included in Prime Try Before You Buy so you can give them a trial run if you're a member!
Promising review: "OMG!! Literally the best! Sizing was true to size. They're thick, not see through. They're EXACTLY like Spanx. I had a pair of the Spanx leggings and lost them. I ordered these last minute for my vacation and I was shocked at the quality for the price. Buy it! You will not regret it!" —Boca Doce Baking
Get it from Amazon for $69.31 (available in sizes XS–4XL and in four colors).
5. A pair of casual wide-leg overalls because it's breezy enough to wear in late summer, but will seamlessly transition into fall when you swap out the under layer for something cozy.
Because these are 100% cotton, reviewers recommend sizing up to account for shrinking or sticking with your regular size and line drying them.
Promising review: "I own these in several colors. You can dress them up for nicer casual occasions, but they’re also casual and comfortable for cleaning the house and an easy slip-on and cover-up after swimming or hiking. I definitely recommend sizing up a size because they do shrink." —LeighBeez
Get it from Amazon for $32.99 (available in sizes XS–5XL and in 20 colors).
6. A flannel plaid shacket to live out your full autumnal agenda in a versatile layering piece that adds warmth (but not too much) and was basically made for apple cider sipping and pumpkin patch adventures.
Reviewers say this runs large so, depending on the type of fit you're going for, you may want to order a size down.
Promising review: "Super cute and oversized for pairing with any outfit. Got the green for St. Patrick’s day then ordered black because I loved it so much. Large was super comfy and cute with a black bodysuit under it!" —Lindsey Daniels
Get it from Amazon for $29.99 (available in sizes XS–XXL and in 13 colors/styles).
7. A three-pack of fall-themed stud earrings so you can add a sprinkle of cozy fall vibes to any look, even if it's 85 degrees and you're forced into shorts.
Honest Outlaws is an Etsy shop based in Loveland, Colorado run by a husband-and-wife team that sells a delightful selection of handmade earrings.
Promising review: "Omg! I squealed when I opened the box...they are just too adorable! I will definitely be ordering again." —Julie
Get it from Honest Outlaws on Etsy for $16.99.
8. An oversized houndstooth sweater vest for updating your summer jeans and T-shirt uniform with a cozy, lightweight layer that's fit for fall.
Promising review: "Love this! Well worth the price! I paired it with a white turtleneck underneath but the options are limitless here. I was surprised at the quality of this item...it’s very soft and thick, which isn’t what I expected at all. Would definitely, and might, buy again very soon!" —Jon Evans
Get it from Amazon for $28.99+ (available in sizes S–L and in11 styles).
9. A cotton dickey collar if you hate the bulkiness off a long undershirt but live for a polished collar peeking out underneath your favorite sweater. Now you can get the layered looks you crave without overheating.
Promising review: "It’s a good value, fits nicely in the 'V' of a sweater. The underarm straps are comfortable and a nice addition to the dickey of the old days. The length is long enough for a deeper V sweater but would not work for a button down cardigan sweater. For the money don’t hesitate to give it to try." —Duffy
Get it from Amazon for $8.99+ (available in four styles and in multipacks).
10. A pullover striped sweater to ease you into sweater weather with a lightweight style that's not too hot, but still oozes fall vibes.
Promising review: "I had three random people tell me, 'I love your sweater!' the first time I wore it! It’s not thick, which makes it perfect for the in-between weather days of south Louisiana when you can’t decide if it’s truly fall or summer still!" —Terrie M.
Get it from Amazon for $39.99 (available in sizes S–XXL and in 27 styles).
11. These high-waisted palazzo pants for tricking people into thinking you tried really hard on your outfit when really you just swapped your skinny jeans for a bit of wide-legged volume.
Promising review: "I’m so impressed by these! The quality is amazing. I love the material. Not sheer at all and super comfortable. I purchased them to wear for work but they would be super cute dressed up with heels and a bodysuit for a night out. I’ll be ordering in more colors as they are already a staple in my work wardrobe! I purchased the color Mocha first and it’s exactly like in the photos — kind of a warm gray color. Highly recommend." —Skylar
Get it from Amazon for $33.99+ (available in sizes XS–2X, as well as short sizes, and in 32 styles).
12. An oversized pale pink hoodie that grants you membership into an elite group of people with the same autumn plans as you — the Cancel All My Plans Club.
The fit is designed to be oversized, so size down if you want a slimmer fit.
Get it from our Goodful shop for $63 (originally $79; available in sizes S–XXL).
13. An A-line woolen midi skirt if your cool weather wardrobe consists of jeans, jeans, and more jeans. This skirt will give your go-to looks a refresh, and the elastic waistband doesn't hurt either. 😏
Promising review: "This skirt is so luxurious! It's soft to the touch, the fabric is thick and warm, the length is long (to my ankles), it's a beautiful print, and it has a stretchy waistband...just gorgeous! I will definitely be buying more in different colors. I purchased the XL and it fits perfectly." —Monica
Get it from Amazon for $36.98+ (available in sizes XS–3XL and in 36 styles).
14. A pack of knit over-the-knee socks because all your favorite dresses and skirts aren't going to cold weather-proof themselves! Don't worry, these babies got some stretch so they can accommodate a wide range of sizes.
TeeHee Socks is a small biz creating fun and funky socks in a wide range of styles to complement your look.
Promising review: "Loved these socks. They are nicely made and look 👀 soooooo cute on!! These are the perfect socks for boots for that in-style look we all love. I was worried because I've got some meat on my bones and didn’t know if these would be too tight but they fit just fine and stretch nicely. These socks are sooo cute and perfect. Get them you will love them!!" —Luv2shopp
Get a three-pack from Amazon for $21.99+ (available in a variety of styles and pack sizes).
15. A V-neck adjustable wrap blouse you can wear on or off the shoulders if you're more than ready to tuck your tank tops away for another year and don a dramatic, billowing long sleeve.
Promising review: "This top is so much better than I had anticipated. The fabric, the quality, the cut, comfort, and versatility are superb!!! I’m so happy. I’ll def be ordering a few more colors. Do it! You won’t regret it. FYI: The wraparound style makes it super easy to wear normally or off the shoulder and your placement can be exactly where you want. I can’t give this top enough ⭐️⭐️⭐️⭐️⭐️" —Daniel
Get it from Amazon for $55.99+ (available in sizes XS–XL and in 11 colors).
16. A faux leather moto jacket to add just the right amount of warmth (and attitude) to your fit without looking overly bundled up on kinda-hot-kinda-cold fall days.
FYI, this is included in Prime Try Before You Buy so you can give it a trial run if you're a member!
Be sure to double-check the size chart for your specific measurements! Some reviewers recommend sizing up, especially if you want to layer bulkier clothes underneath.
Promising review: "This jacket is fantastic! The faux leather is very soft, it looks amazing and the fit is spot on! I’ve worn it a few times and received compliments each time. I love it so much, I’m ordering more colors!" —Peacedolphin22
Get it from Amazon for $48.99+ (available in sizes S–XXL and in 19 styles).
17. A crewneck spooky season sweatshirt for anyone interested in playing the part of Halloween PR rep and spreading holiday cheer (or fright) to everyone you encounter.
Hello Handpressed is a Spokane Valley, Washington-based Etsy shop run by a husband and wife duo. The pair hand presses too cute graphic prints on quality apparel.
Promising review: "I loved this sweater so much I ordered three other sweaters! It looks just like the pictures and it was super soft!" —wyndzer
Get it from Hello Handpressed on Etsy for $35.93+ (available in unisex sizes S–4XL and in 22 colors).
18. These stylish tassel loafers with thick rubber lug soles so you can hop on one of this fall's hottest footwear trends without sacrificing your feet to an uncomfy fate.
FYI, this is included in Prime Try Before You Buy so you can give them a trial run if you're a member!
Promising review: "I needed a pair of dressy shoes to wear with my suits on days when I have to walk a lot. These shoes look sharp and they are so comfortable. I can walk all day in these, and guess what, they look great with jeans, too! I feel like I have a spring in my step when I'm walking in these and I get so many compliments. I am ecstatic with this purchase. They fit perfect, too, which I was a bit worried about." —Jane Jernigan
Get it from Amazon for $76+ (available in standard sizes 5–13, wide sizes 6–10, and in nine styles).
19. An oversized turtleneck sweater dress that'll put to rest any argument that dresses can't be cozy. Pair it with leggings or your favorite showstopping boots.
Promising review: "OMG, where do I start. I love this dress. It’s so big and chunky and cozy but also super sexy!!! The pockets are amazing, and the material isn’t itchy at all. It looks great paired with tall boots, but I’m sure you could rock some leggings and ankle boots and it would look just as amazing. Totally worth the price; it is baggy for sure, but I anticipated that when I ordered one size up so I could get the length I wanted. I want one in EVERY COLOR. Another Amazon win!" —Ashlee
Get it from Amazon for $41.99+ (available in sizes S–3XL and in 43 styles).
20. A daisy-covered cardigan for cozying up basically any outfit with a punch of color and Y2K flair.
Reviewers who typically wear sizes S–L seemed to have success with this "one size" cardi.
Promising review: "This is so much nicer than I expected. It's very warm and very soft. I was honestly expecting it to be very thin and rough like most knit sweaters and I was pleasantly surprised that it was quite the opposite! And its complete coverage! No holes that show your undershirt!" —Yahari
Get it from Amazon for $25.99+ (available in one size and seven colors).
21. A ribbed balloon-sleeve top if you're on the hunt for the perfect slouchy shirt to basically spend every waking moment in this fall.
Promising review: "Absolutely fantastic top! It’s warm enough for cool weather in fall and winter (subtropics) but light enough for spring. It’s soft and comfortable, drapes very cute, and looks good. Great color of blue." —Julie
Get it from Amazon for $34.99 (available in sizes S–XL and in 27 colors).
22. Or a V-neck waffle knit top that's equally comfy but has a little added structure with the cute tie-front detailing.
23. A flowy long sleeve maxi dress to ride out those not-quite-fall, not-quite-summer days in a printed piece you could just as easily pair with espadrille sandals as you could your favorite boots.
Promising review: "I bought it as a versatile dress to wear for fancy or casual occasions. It’s so easy to throw on and run out the door, and automatically look put together. I have used it with the included belt as well as belts I already have. I love that it does not have the little belt loops that stick out and make dresses look cheap." —JaymeInOhio
Get it from Amazon for $38.99 (available in sizes S–XL and in 12 styles).
24. A workwear-inspired short-sleeve jumpsuit in a picture-perfect autumnal hue so you can skip finding a top to match your bottoms and just slip into a one-and-done outfit that's built for just about any adventure you could imagine.
Big Bud Press is a Los Angeles-based small business creating quality, ethically made unisex clothes for living out your day to day. The majority of their fabrics are knit/woven locally, they visit each branch of their manufacturing minimum once a week (but usually more), and all of their dyes and non-toxic.
Get it from Big Bud Press for $210 (available in unisex sizes XXS–6XL and in additional colors).
25. A knit long-sleeve dress with cute button detailing that's the perfect accessory to your favorite leggings when you want to look put-together without a whole lot of fuss.
FYI, this is included in Prime Try Before You Buy so you can give them a trial run if you're a member! Also, reviewers say this dress runs large, so consider ordering a size down!
Promising review: "Love the comfort and ease of this dress. I wear it with leggings. Washes and dries easily, no shrinkage or wrinkling! Maybe the pockets weren’t necessary, there is a slight bit of bulk on one side, but not noticeable and who doesn’t like pockets?!?! Jewelry with this is limitless; easy to style. Definitely buying again in another color." —MoInnkeeper
Get it from Amazon for $32.99 (available in sizes S–XXL and in 28 styles).