Unless otherwise specified, all sizes in this post are listed in women’s.
1. A pair of black floral tights to give your dresses and skirts the easiest (and dreamiest!) fall upgrade by making it look like you just stepped out of a magical pumpkin patch.
2. A pullover crewneck sweatshirt perfect for layering in cold offices or for your next Gilmore Girls marathon.
3. A relaxed fit black blazer for giving your fall dark-academia vibes a TOTAL autumnal boost. Reviewers say this particular blazer runs lighter in weight, which is PERFECT for early fall days where the sun is still doing its thing a little *too* well.
4. A button-front cardigan that is basically a cozy blanket that doubles as an “I’m an adult person” accessory.
5. A mock turtleneck A-line dress if you want to herald in the new season with a touch of Kathleen Kelly’s You’ve Got Mail wardrobe in your own cozy closet arsenal.
Target
Promising review: “I love how comfortable the dress is, and the pockets are an added bonus!” —Taramomteacher
Price: $35 ( available in sizes XS–4X and in three colors)
6. Some high-rise cropped wide-leg pants so you can look sleek and fashionable without a bunch of fabric feeling too tight on your legs. These neutrals are giving autumnal but also can be brightened up with a pop of color in the form of a cardigan.
Target
And don’t forget the matching top to go with them!!
Promising review: “Perfect, flowy, casual pant for spring and summer! Proportionate through waist and thighs. The high-rise is perfect, and I felt so comfortable with a tank tucked in, not worried about the pants rolling down. Please make in more colors and full pant length.” —Tamagaal
Price: $30 (available in sizes XXL–3X and in two colors)
7. A denim maxi skirt for when the weather starts to turn hoa hoa hoa outside. (Where are my Twilight friends at?? Bella totally rocked this skirt in the books, and YOU KNOW WHAT? ICON.)
Target
Promising reviews: “Comfy and perfect. I absolutely love this skirt I will wear all summer, fall, and spring.” —GirlMom
“This denim skirt is absolutely perfect! It has a comfortable stretch to it and not stiff and awkward like most denim skirts. I highly recommend!” —Ambnova
Price: $36 (available in sizes 00–30 and in four washes)
8. Or an A-line maxi skirt to bring a touch of swooshy cool-weather-picnic vibes to your wardrobe. (And this would also look darling with your new cardigan!)
Target
Promising reviews: “It’s super cute and comfy. I love it. The length is perfect and the color is exactly the same as the picture.” —Skirt
“This is the best skirt I’ve ever owned! I got it in both colors. The fabric is amazing and soft, the fit is perfect. I have it at my navel and still have about an inch off the ground. So it doesn’t drag. I wish there were more!” —Kei
Price: $28 (available in sizes XS–4X and in two styles)
9. A short sleeve belted midi shirtdress that is every worker bee’s go-to comfy fall outfit because it’s like wearing a big sleep tee but to official business places.
Target
Promising reviews: “Nice quality! Cute belted or unbelted. The color and weight of the fabric will be great for fall too! I sized up for an oversized look.” —Midwest
“Beautiful dress! Love how it flows when you move and the quality of the fabric. Great dress for summer that could easily transition into the fall.” —Onetiredmama
Price: $35 (available in sizes XS–XXL and in three styles)
10. A pair of high-rise and wide-leg gauze pull-on pants reviewers love for their versatility and snuggly abilities.
Target
Promising reviews: “Easy, breezy, comfy pants that will transition easily into fall.” —Kellydenn1977
“The pants are so comfortable. Great travel pants. They were very long but I took them to get altered. I received many compliments on the matching outfit.” —EMA
Price: $30 (available in sizes XS–4X and in three colors)
11. Or some high-rise fold over fleece pants if you’re after a little more warmth in your cozy pants game.
Target
Promising review: “These are SO soft and SO comfortable. Just the right amount of ‘Baggy.’ In my opinion, they do run large in the waist, but have a drawstring. The only con is they are easily 3” too long on me, and get bunched up under my feet/shoes.” —Hmnrn
Price: $25 (available in sizes XXS–4X and in six colors)
12. A V-neck denim vest for throwing over your fave fall dress to ~add a little spice to it.~
13. A French terry cardigan because the chunky knit oversized look is even more eternal than sneakers-with-everything and this one gives serious curl-up-with-a-book-and-look-great-doing-it vibes.
Target
Promising review: “Soooooo soft and comfy my go-to cardigan to wear over business casual clothing for meetings or in the house lounging around.” —Gatort90
Price: $32 (available in sizes XS–4X and in two colors)
14. A butter romper you can wear all on its own or layer up to tailgating and football games because you know sometimes—and I’m gonna hold your hand when I say this — fall can still have one last gasp of hot air. Look cute and seasonally festive without melting in the stands!
15. A V-neck pullover tunic sweater that wants to come with you to any and all sporting events to keep you looking sporty and feeling snug all football season long. (Go Taylor’s boyfriend!)
16. A pair of linen cargo pants in colors that can go with literally anything which is GREAT because we love being very demure, very mindful with our pumpkin spice season outfits.
17. A pair of mid-rise ’90s baggy jeans comfy and able to tie your outfit together in a way that even the strict ’90s sitcom moms would approve of. Get your disapproving look ready for the “my kid snuck out on Halloween” episode.
Target
Promising review: “These jeans are so good! This review is for dark-wash cuffed jeans. They are a tad bit snug in the waist but baggy and loose from the hip through the leg. The cuff is sewn in, so no worries about it coming undone. Good weight denim, and the perfect pair of jeans! I love them!” —Toni
Price: $36 (available in sizes 00–30, three lengths, and in six washes)
18. And a ’90s baggy trucker denim jacket if you really want to commit to the baggy/comfy/trendy bit. (And trust me, you do!)
19. A striped cardigan because you really can’t have too many long-sleeved comfy options when the temperatures start to drop.
Target
Promising reviews: “Very comfortable and high quality. Fits well!” —sge1212
“I bought this in red and loved it. So I had to have it in black as well. It’s soft and stylish and even the buttons look expensive. I highly recommend it!” —soft sweater
Price: $35 (available in sizes XS–4X and in two colors)
20. A midi sheath dress in colors that just scream “WELCOME, FALL” while also being put-together enough to wear to work or out on a cute pumpkin-y date.
21. A short-sleeve tee for tossing on with a skirt or your baggy jeans for a casual, easy go-to outfit that will have you out the door to fall farmers markets and flea markets all the faster.
Target
Promising reviews: “The best everyday basic tee! These are so soft and cozy, they fit true to size, and wash well. I hang dry them and they’re still in perfect condition after repeated washes.” —Agk23
“Working my way up to owning every color of these! Such a great basic and can be worn with anything. Love tucking them into jeans or a midi skirt.” —jaclyn1993
Price: $6 (available in sizes XS–4X and in 15 colors)
22. A waffle robe because when it comes to our excitement about peak lounging weather, we’re not wafflin’.
Target
Promising review: “Great price. I’ve been looking for a waffle robe. This one washed up well and is soft and lightweight. I sized up to give an oversized spa feel. It’s a mix of cotton and polyester so it didn’t shrink in the wash like the last one I bought from another store. This one is a keeper. I purchased the light grey. I’m 5’4″ and the length falls just below my knee cap.” —Comfycozy
Price: $35 (available in sizes XS/S–3X/4X and in two colors)
23. And a short satin pajama set to go beneath it. (Psst. I’ve seen more than one person buy sets just like this on TikTok recently who wear the top out as a regular around-town satin top, too!)
Target
Promising review: “I’m so obsessed with these that I bought a backup pair! They are so soft and cozy, and fit true to size. I have washed and dried these and they didn’t shrink at all!” —averybclark
Price: $25 (available in sizes XS–4X and in two colors)
24. A pair of high-rise flutter shorts if the cooler weather has you ready to hit the trails, the park, or anything in between. Comfortable and reminiscent of a Taylor Swift Eras Tour costume??? Please and thank you.
25. Some high-waisted ButterBliss leggings that will keep your legs as warm as your heart when you get your hands on your first autumn beverage.
Target
Promising reviews: “These leggings are buttery soft and very comfortable. I have several pairs. I like that they are high-waisted, they offer the right amount of compression.” —Maria C
“These are one of the best leggings I have gotten in a long time. They are very soft good quality and not see-through.” —Liza
Price: $18 (available in sizes XXS–4X)
26. A long-sleeve utility baggy denim jumpsuit because the denim-on-denim moment is back and we love to see it fall and all year, frankly.
Target
Promising reviews: “I buy this denim jumper every year. Hope they make one in black. It is so comfortable and you can dress it up or down. And the price is very reasonable. Can’t wait to wear it.” —MAR
“Buy it! Great quality, TTS. Looks even better in person! This is as good as the Aritzia denim jumpsuit but a fraction of the price.” —Bossmommie
Price: $44 (available in sizes 00–30 and in two colors)
27. And finally, a good ol’ fashioned cropped full zip hoodie to keep you snuggly on any planes, trains, or automobiles you find yourself traveling on for your autumn travels.
Target
Promising review: “I wanted an oversized slouchy zip up and this was the perfect one. It does fit TTS so I sized up one to get the loose fit I wanted. Has held up great and I ended up ordering more colors because I wear it so much.” —guessr
Price: $18+ (originally $30, available in sizes XS–4X and in four colors)
Reviews have been edited for length and/or clarity.
