Unless otherwise specified, all sizes in this post are listed in women's.
1. A turtleneck bodysuit that reviewers say is not too thin and not too thick because we love a transitional piece between the warmer months and the cooler time of the year.
Promising review: "This bodysuit is so comfortable! I've been looking for a bodysuit for a few skirts...you know, one that didn't result in a wedgie. I was so happy to be able to wear this bodysuit literally all day without it trying to floss me! Absolutely recommend this garment!!! And it looks cute in fall photos!" —Pullin' Reviews
Get it from Amazon for $17.99+ (available in sizes S–XXL and in 12 colors).
2. A pair of wide-leg stripe pants with a fun retro flare if you're into looking ridiculously chic while still feeling ridiculously comfortable. The best of both worlds, right?
Promising review: "I’ve been waiting my entire life for these pants. They’re comfy but also very stylish. Perfect for work or a weekend out. The length is amazing (even for a 5'10" woman). I plan on wearing them every day!" —Amy K.
Get it from Universal Standard for $145 (available in sizes 00–40 and in seven color combinations).
3. A pair of platform ankle boots designed with a stretch knit around the ankle, making them super easy to pull on and off, so you can wear them to the airport and not have to have a mini panic attack when you get to TSA.
Promising review: "These boots fit perfectly. I am a 7.5 in Steve Madden, and these fit TTS. The quality is great so far, and they are super comfy. GET these for fall!!" —Bailey Earp
Get them from Amazon for $48.98+ (available in sizes 5–11 and in 19 colors).
4. A pair of overalls if you're a farmer, an artist, a barista, or anyone who is on their feet a lot and wants to be comfy and look cute at the same time. These are basically like wearing an adult onesie...what's NOT to like?!
Promising review: "If you've been hesitant about whether or not to buy these, then this is your official sign to just do it!! I kept these in my 'Saved for later' cart for nearly a year before finally deciding to take the leap. Oh my GOSH, I am so glad I did! These are officially my favorite pair of overalls and absolutely perfect for fall. They're so comfortable, and I most certainly will be ordering more in other colors. So if you're looking to unleash your inner painter/gardener, then this is the perfect outfit for you :D" —Nathan R Ford
Get it from Amazon $26.99+ (available in sizes S–3XL and in 19 colors and patterns).
5. A super-stylish midi skirt made with a rib-knit material, because you want to be prepared when you're invited to a last-minute brunch outing and need something easy and comfortable to wear while still looking chic.
Promising review: "This skirt looks so good on. The color is perfect for fall and winter. I will be pairing it with sweaters. It looks expensive on." —Alicia Adams
Get it from Amazon for $26.99+ (available in sizes XS–XL and in 14 colors).
6. An oversize crewneck for those days that you really don't want to get out of your pajamas, and because for some reason, society has deemed PJs unacceptable in public. This sweater isn't technically sleepwear, but it feels like it! And it's super cute!
Promising review: "I love this sweater and need to buy it in other colors because I wear it way too much. It washes well. I purchased one size larger than normal because I wanted it to cover my rear so I could comfortably wear it with leggings. It’s perfect!" —Mom2_4
Get it from Amazon for $36.99+ (available in sizes XS–XL and in 32 colors and styles).
7. A pair of Everlane's '90s cheeky jeans if you're a millennial who has come to the realization that skinny jeans are no longer "in" but still wants to desperately hang on to the skinny jean feel. As a Gen Z girlie, please just let me help you here.
Promising review: "I have gone through the '90s Cheeky in probably every color (except bone, which is perpetually sold out); they are my favorite jeans I've ever worn in my life. They're comfortable, they fit like a glove, they're durable, they're adorable, and they go with everything. They run a size large and get looser over time and don't retain their original waist size because they don't have stretch. Just remember that." —Alexx S
Get it from Everlane for $108 (available in sizes 23–33, in three lengths, and in six colors).
8. A striped turtleneck with super-cute button detailing on the shoulders for those times we get invited out on our friend's boat and want to fit in with the nautical theme.
Promising review: "This sweater is very comfortable and easy to pair with different options. It has four buttons on the left shoulder that add to a dressy look. It can be worn with jeans and a pair of boots or with dress pants. It is warm on a cold day and still light enough that it isn't too bulky. Then it is either as expected or slightly big. The sweater is easy to care for and still looks great after a couple of washings! I would buy this sweater in other colors." —Suzan Hornbeck
Get it from Amazon for $42.99+ (available in sizes S–XL and in 26 colors).
9. A leopard-print slip midi skirt to pay homage to the OG fashion icons: the Cheetah Girls. Pair with some hoop earrings, a denim vest, a low-slung belt, and a fedora, and you might as well be their fifth member.
Promising review: "This is by far one of my favorite purchases. It's an awesome skirt, and the price was unbelievable. I'm so happy I purchased this. It looks way more expensive than it is. I get tons of compliments every time I wear it. Buy it; you won’t be disappointed." —Jen Francis
Get it from Amazon for $28.99 (available in sizes XS–XL and 11 colors).
10. A fuzzy three-piece loungewear set for when you want to get in some lazy "bed rotting" but don't want to look like a literal couch gremlin. In these, you'll basically be chillaxin' like a Kardashian.
Promising review: "I love this outfit. This has become my go-to when I don’t feel like getting 'dressed' when lying around the house, but still want to feel somewhat put together and not look frumpy. It’s super soft, warm, but not too warm. It’s really cute." —Danielle Weiss
Get the three-piece set from Amazon for $53.99+ (available in sizes S–XL and in 30 colors and styles).
11. An off-the-shoulder V-neck blouse made of a soft and stretchy fabric with a super-stylish silhouette if you're looking to pair something ~slightly~ fancy with your fave pair of jeans.
Reviewers do say it runs small, so size up.
Promising review: "This blouse is so elegant! It fits well, but it runs a bit small/tight, so ordering up would be ideal. It’s also versatile, and the material is extremely soft. It has little stretch, but again, I would recommend it. The color is so nice too. I used it for a photo shoot, and it just popped!" —Gesselle Walters
Get it from Amazon for $28.99+ (available in sizes XS–XXL and in 16 colors and sleeve lengths).
12. A chunky knit button-front cardigan you're going to basically live in this fall and winter. You can wear it on its own as a chic top of over your favorite tee, making it the perfect layering piece.
Promising review: "I love this neutral taupe heathery color; it’s so much prettier in person. The material is very nice — not too heavy, not too light; it’s truly a perfect fall cardigan or as a layering piece. I’m more like petite size, so it’s hard to find a right-length cardigan. I ordered this in XS; fits great. I also got the matching cropped tank." —Ron Y.
Get it from Amazon for $54.90 (available in sizes XXS–5X and in eight colors).
13. A crew-neck sweatshirt that screams "off-duty model." Whether you wear this to go grocery shopping or pick up your kids from school, everyone will be thinking, "Wait are they famous??"
Promising review: "I love this sweater! I didn't realize that it wasn't brushed on the inside. The inside is more like a rougher towel texture. But it isn't bad. I actually prefer that sometimes because I am notoriously always hot." —TK
Get it from H&M for $24.99 (available in sizes XS–XXL and in six colors).
14. A striped button-down shirtdress because you want to honor one of your favorite spooky characters this Halloween season. Just make sure not to say Beetlejuice three times while you wear it!
Promising review: "For the price, this dress is WONDERFUL. I ordered according to my measurements to fit the bust so it would not pop or gap at buttons. The waist was not too large but will look better with a belt. GREAT for use as a Beetlejuice-inspired look for Halloween and then useful after!" —MrsStricklen
Get it from Amazon for $29.98+ (available in sizes 2–24 and in 10 colors and patterns).
15. A broken-in baseball cap if you're having a bad hair day and want to be able to leave the house without looking like a cartoon who just got electrocuted.
Promising review: "This cap is so perfect, and you can throw it on with any outfit! I got the beige one, and my sister got the white baseball cap. Both are such staples in our wardrobe now! And the fit is perfect. I love the little brown leather adjustable strap in the back; very luxe and high quality." —SAM97
Get it from Madewell for $12.99+ (originally $29.50; available in one size and in nine colors).
16. A lightweight maxi shirtdress that you can wear to work and during a night out on the town. Ideal for when you have a date directly after your nine-to-five and don't have time to go home and change.
Promising review: "Lovely! It was a bit big in the midsection, but I bought it oversize on purpose. It looks great with my chunky and thin belts! It's perfect for all seasons. I intend on wearing it this summer and then adding leggings for fall." —AMA
Get it from Amazon for $31.88+ (available in sizes XS–XXL and in 16 colors).
17. A pair of Sam Edelman loafers you can ~slide~ right into to elevate any outfit. These would also look amazing with the shift dress above for a classy casual fall look!
Promising review: "These shoes are a favorite! I ordered the black after having a beet red color for about a year and a half. They were comfortable right out of the box, the leather is supple, and they look high quality. I am very happy with my purchase. These are often compared to the Brixton loafer from a high-end fashion brand." —Christine
Get them from Amazon for $150 (available in sizes 4–14, in wide width, and in 49 colors and patterns).
18. A long-sleeved V-neck ribbed sweater I feel like Bella Swan would totally rock. Just pair it with a grey hoodie, a pair of Converse, and a mildly confused expression and you'll be living your Forks, Washington fantasy.
Promising review: "This is a very high-quality sweater! The material is thick and warm and soft. It's very well made and comfortable. The color is beautiful. I ordered the brown and black one in the XL, and it fits me great." —Michele D.
Get it from Amazon for $33.99 (available in sizes S–XXL and in 25 colors and patterns).
19. A Princess Diana embroidered sweatshirt showing her in her *iconic* revenge dress so you can feel comfy and cozy but still remind people you are not to be messed with.
Viable NYC is a woman-owned small business based in New York!
When I came across this sweatshirt while scrolling TikTok, I just knew I HAD to own it. I've loved Princess Diana for years now, and this look is unmatched. And ever since this sweatshirt arrived, I basically haven't taken it off my body. It is so perfect. It's soft and comfortable and yet so chic. I paired it with my faux-leather shorts to show a more dressed-up look. If you're a fan of Diana, you NEED this sweatshirt. Or check out the other designs in the shop, because there are so many other great styles.
Get it from Viable NYC on Etsy for $53+ (available in unisex sizes S–4X and in two styles).
20. A lightweight shacket reviewers love for its fit, warmth, and style. This is ideal for those fall days when you wake up and it's chilly outside but then somehow it's 75 degrees by lunch.
Promising review: "I saw this on TikTok, and I was hesitant at first, but I bought it. I’m really small, so I bought the medium to be oversize, and it’s great. I could definitely fit smaller sizes and it would still be big, so if you want the sleeves smaller, I’d size down. So comfortable and cute, especially with bodycon dresses." —Bela Maria
Get it from Amazon for $29.99+ (available in men's sizes S–3XL and in 13 colors).
21. A pair of palazzo pants if you're wanting to look stylish and put together but skirts and dresses aren't exactly your thing. Plus, these look incredibly comfortable, IMO.
Promising review: "I don't typically wear flowy clothing, but these looked comfortable and stylish, so I took a chance. Once I put them on, I didn't want to take them off! They are very comfortable, and I love the color. My husband even commented that I should get them in more colors, since I like them so much. I wore them to an upscale tearoom event and received a lot of compliments." —World Changer
Get them from Amazon for $33.99+ (available in sizes XS–2X, in short, and in 32 colors/patterns).
22. These Polarized vintage-inspired sunglasses because you want to block out the haters (and the sun) while also lookin' good as hell.
Promising review: "OBSESSED!!!! They’re sooo cute! They look super high end and expensive. They’re very lightweight and fashionable. I love everything about them. They came in the cutest box and came with a drawstring bag to hold them in and a lens cloth! Love, love, love!" —Tianna
Get it from Amazon for $25+ (available in 11 colors and also in sets of two).
23. A gingham anorak with an adjustable drawstring in the waist, meaning you can wear it two different ways. Believe me when I say, once the temperature hits below 60, you're never gonna wanna take this thing off.
Get it from M.M.LaFleur for $150 (orignally $495; available in sizes XS–XXL).
24. A V-neck pleated tunic that has incredible twirling potential, so you can feel like the center of attention when everyone is asking you where you got it.
Promising review: "This is a great transition dress for fall. I would say with the baby doll fit, it is a loose dress, which is to be expected for the style. I loved it so much, I ordered two other colors!" —Marci
Get it from Amazon for $27.18+ (available in sizes S–XXL and in 41 colors, patterns, and sleeve lengths).
25. A detachable shirt collar because spooky season is coming up and you want to turn every skirt you own into a Wednesday Adams look.
Promising review: "Must-have life hack! I saw someone get this off of TikTok, and I totally loved it. It does exactly what you’d want it to do. The shirt can unbutton if you need it to; it’s super easy to put on. I love that it gives the illusion that I have a collared shirt under it without the hassle of wearing an actual collared shirt!!" —Danny
Get it from Amazon for $8.99 (available in three colors and in round and pointed collars).
26. A swoop-neck top with a built-in bra because, let's be honest, it is nearly impossible to find the perfect strapless bra, and with this, you don't have to!
Buzzoms is a Black woman–owned small business creating clothes with a "boob pocket" in them so you can ditch your bra. The pocket is made with a breathable mesh material with an elastic band underneath to hold everything in place.
Get it from Buzzoms for $70 (available in sizes 0–5 and in olive, black, and tan).
27. A chic monochromatic sweater and pencil skirt set for when you're putting an outfit together but can't be bothered to find pieces that match. Just throw this ensemble on, and you'll be ready to go!
Promising review: "I love this set. The quality is good. The skirt is a bit thinner than the sweater, so I wore Spanx underneath. It’s soft, warm, and cozy. The material isn’t itchy. I will have these pieces on repeat. It’s also Pantone’s color of the year. Buy it!" —Amazon Customer
Get it from Amazon for $47.92+ (available in sizes XS–XXL and in five colors).
28. A strapless mesh bustier that you'll feel very smug telling people is from Amazon because it looks so much more expensive than its price tag. Time to serve some Hailey Bieber realness in this beauty!
Promising review: "Perfect and versatile. This fit like a glove. I wore to a birthday celebration and I felt super secure and comfortable and chic. Will be a repeat outfit offender and wearing this piece in so many different ways." —Princess
Get it from Amazon for $26.99+ (available in sizes 00–20 and 19 colors).
29. And finally, a button-down baby doll dress in denim if you want to look like a fashionable cowgirl but have never actually seen a cow IRL (and if that's the case, you really should try to see one sometime. Cows are great). But don't worry — you can wear this on and off the farm!
The reviews for this post have been edited for length and clarity.