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

1. A denim oversize Western jacket with a slouchy silhouette that layers ~perfectly~ over slip dresses, knits, and everything in between. It's pretty much the sartorial equivalent of open skies, road trips, and sunsets fading slow.

Madewell

Price: $108 (available in sizes XXS–XL)

2. A relaxed V-neck polo shirt that’s unbe-leaf-ably stylish and will have you raking in the compliments throughout the season. 🍂 Pair it with jeans, trousers, or layered beneath a cozy blazer. The options here are truly endless, people.

Madewell

Promising review: "Very soft. Super cute. I think this will be a fall staple. I love the subtle shimmer thread!" —Yaymeee

Price: $68 (available in sizes XXS–XXL and three colors)

3. A button-front cashmere cardigan so stylish and soft, you'll probably want to wear it every day when fall's here. This transitional beauty layers well with a baby tee, cami, or tank, plus keeps you warm if it's a slightly chilly day.

Madewell

Promising review: "I absolutely adore this soft cardigan. It’s incredibly warm, and the color complements my olive skin tone perfectly. I can’t wait to wear this sweater for years to come." —Daly

Price: $198 (available in sizes XXS–XXL and four colors)

4. Chelsea boots with a snipped toe and kitten heel because sometimes you need just enough edge to sharpen a floral dress, just enough height to elevate your jeans, and just enough attitude to take you from boardroom to bar without missing a beat. Meet the Goldilocks of fall business casual boots.

Madewell

Price: $218(available in sizes 5–12 and four colors)

5. Corduroy high-rise balloon pants if your fall daydreams involve bookstore browses, chai lattes, and leaves crunching underfoot. Their billowy silhouette makes every sidewalk strut feel like a scene straight out of your favorite indie flick.

Madewell

Promising review: "The corduroy balloon pant is a really cute addition for the colder months ahead. The fabric is lightweight while also being cozy. Would love more colors." —Style Mama

Price: $138 (available in standard sizes 23–33, 14W–20W, and in green)

6. A long-sleeve gingham top with clean lines and timeless checks, easy to tuck, layer, and wear on repeat from September to December (and beyond).

Madewell

Price: $72 (available in sizes XXS–3X)

7. Easy-going, highly rated straight jeans reviewers swear are the perfect fit, crafted from premium 100% cotton denim with that old-school character you can’t fake.

Madewell

Promising review: "I have bought two pairs in the last couple of weeks. The fit is perfect. I love, love, love these jeans. I recommend them to anyone, any size, they are awesome!" —Lorri

Price: $148 (available in sizes 23–33, 14W–24W, petite and tall sizes, and nine colors/washes)

8. And an oval buckle belt to go with, and instantly jazz them up. It's the kind of no-fuss accessory that makes even a plain tee look styled on purpose.

Madewell

Promising review: "I LOVE this belt; it’s a simple and chic addition to an outfit, and the woven pattern allows for variability, like cinching a dress at waist height." —Abbycn

Price: $78+ (available in sizes XXS–XXL and five colors/patterns)

9. A cozy cashmere V-neck sweater vest for when you want to look scholarly Fall Semester chic without ever cracking open a single syllabus. Ivy League energy with no acceptance rate? Sign me up.

Madewell

Promising review: "I have tried so many sweater vests trying to get that right slightly oversize fit. All are too loose or too tight in the wrong places, don't have the right feel, or fit weird on the shoulders. This one is super soft and light, great quality, and drapes exactly perfectly! The sizing is perfect, go with your true size for a comfortable fit!" —Jill

Price: $148 (available in sizes XXS–XXL and three colors)

10. A plaid smocked waist mini skirt made from a lightweight cotton voile if your weekend plans involve apple picking, brunch with friends, and pretending your life is a rom-com set to a crunchy-leaf soundtrack.

Madewell

Price: $98 (available in sizes XXS–XXL)

11. A wool baseball cap to keep your gorgeous face shielded from the sun and it goes well with all your cap-tivating fall ensembles. 🧢

Madewell

Price: $45 (also available in navy blue)

12. A '70s-style fringe shirt-jacket crafted from 100% suede well worth the splurge since it’s the kind of forever piece that, like a fine vintage wine or great record, only gets better with age.

Madewell

Some reviewers say it runs big, so you might want to size down for a more fitted look.

Promising review: "I am 5'11 and have broad shoulders. It is a cute jacket and I look forward to wearing it this fall!" —Sarah

Price: $625 (available in sizes S–XL)

13. A gathered button-front floral midi dress with blessed pockets because who needs a purse when your outfit’s already doing the most? Wear it solo on sunny days or layered with a cardigan when the breeze hits.

Madewell

Promising review: "I love this fabric. This dress is so cute, and the slightly longer length in the back is very nice. It's a bit more fancy, so it'll be perfect for a dinner out." —Mich

Price: $148 (available in sizes XXS–XXL)

14. A crisp poplin button-up shirt that has clean lines, tailored ease, and endless styling potential. You'll be collar-ing all the compliments in this baby.

Madewell

Promising review: "Cute, versatile blouse. Fabric is crisp and attractive. Summer blouse that can move easily into cooler weather!" —Nancy

Price: $59.99+ (originally $98; available in sizes XXS–XXL and seven colors/patterns)

15. A flared denim midi skirt with roomy side pockets for a modern spin on a timeless silhouette. You’ll wonder how you ever skirted by through life without it.

Madewell

Price: $148 (available in sizes 14W–20W)

16. A stylish zip-front jacket you’ll throw on for everything — coffee runs, concerts, date nights, and those in-between days when you want effortless polish with zero effort.

Madewell

Note: Some reviewers say this jacket runs big!

Promising review: "My search for the perfect fall jacket is over! Very comfortable and roomy enough for a sweater underneath. Lightweight but provides enough warmth for chilly fall days. Love it!!" —Julie Z

Price: $218 (available in sizes XXS–XXL, 2X–3X, and in molasses brown)

17. Bestselling ballet flat mules that your group chat will get a real kick out of seeing you in all the time, as they're comfy, durable, and versatile enough to keep up with every plan on your busy social calendar.

Madewell

Promising review: "I bought the red suede color on sale, they are SO comfortable and chic. I couldn’t be more obsessed! and now great, I want every color lol. I’m a 9 in Madewell shoes and these fit perfectly in my usual size." —MWMWMS

Price: $69.99+ (originally $98+; available in sizes 5–12 and 10 colors/patterns)

18. A striped elbow-sleeve henley tee so your arms can be covered without feeling stuffy. It's the perfect balance of comfort and ease and goes with practically ALL your bottoms.

Madewell

Promising review: "This T-shirt can be dressed up or down. Looks as good for a casual work day as the weekend. I’ve paired with pants, denim, and athletic pants, and it looks great with all of them." —Tiny Texas

Price: $55 (available in sizes XXS–L and in red)

19. Barrel-leg utility pants that are basically the jean-ius move your fall wardrobe’s been waiting for: roomy, comfy, and proof that function and fashion can totally be soulmates.

Madewell

Price: $128 (available in sizes 14W, 16W, and 20W)

20. A puff-sleeve sweatshirt to snuggle up in with a mug of hot tea, a great book, and the kind of lazy Sunday vibes you wish you could bottle and sample anytime.

Madewell

Price: $95 (available in sizes XXS–XXL and in white)

21. A delightful silk bandana that moonlights as a lightweight scarf, belt, headscarf, or bag accessory. It's so good, you’ll want more than one to mix and match with all your fave OOTDs.

Madewell

Promising review: "Beautiful soft bandana which is a perfect mid-season weight. The colors are great to style with many different outfits. I've worn it with a white shirt for work and just peaking out of the top of a sweater for a more casual look." —Lisa

Price: $49.99+ (originally $68; available in seven colors/patterns)

22. Wide-leg jeans with a delightful retro aesthetic that sway with every step, channeling golden-hour strolls and vintage Polaroid vibes.

Madewell

Promising review: "I have these jeans in the cropped light wash and love them! Decided to buy them in black for fall outfits. They are just sooo good. Material is thick and has a good stretch, and they maintain their form all day and for several wears. For the record, I wash my jeans maybe every fourth wear to maintain the material’s integrity. Get them, you won’t be disappointed" —Oyuki

Price: $148 (available in sizes 23–33, 14W–24W, petite and tall sizes, and five colors/washes)

23. A tie-waist midi shirtdress in a gorgeous midnight navy tone perfect for tackling your inbox by day and raising a glass by night. Just swap the flats for heels and you’re good to go.

Madewell

Price: $158 (available in sizes 00–10 and 14)

24. A stunning lapis heart charm bracelet that shines on its own and gets even better as you add custom charms over the season (hint: the perfect gift from friends come Thanksgiving and beyond).

Madewell

Promising review: "I recently purchased this charm bracelet and I'm absolutely in love with it! It's such a unique and charming piece that stands out from other jewelry I've seen. The quality is fantastic — it feels sturdy and well-made. What I especially love is the little blue heart accent, which adds a perfect pop of color and personality. It's a super cute detail that makes the bracelet feel special. I've already started planning some fall outfits with it, as the style and colors will pair beautifully with cozy sweaters and autumn tones. If you're looking for a high-quality, unique accessory for the upcoming season, I highly recommend this bracelet!" —Acv68

Price: $48

25. A semi-sheer split-neck top in a floral georgette with smocking details which is sheer proof that your closet can still surprise you. Equal parts flirty and floaty, it’s basically a compliment magnet disguised as a blouse.

Madewell

Price: $118 (available in sizes XXS–XXL)

26. A crewneck cutaway denim vest you want your outfit to say "yes, I thrift cool vintage" without actually setting foot in a thrift store.

Madewell

Price: $108 (available in sizes 00–28)

27. And a midi slip skirt with a fun side slit, because sometimes your fall outfit deserves its own little plot twist. It's the kind of cut that really gives your look a leg up in the style department.

Madewell

Price: $98 (available in sizes 00–16 and in black)

Reviews for this post have been edited for length and/or clarity.