Unless otherwise specified, all sizes in this post are listed in women's.
1. A plaid shacket that has a drop-shoulder design, button cuffs, and plenty of room for layering! It's sure to be your comfy go-to for some added warmth.
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: "What’s not to love about this jacket??? It’s soft but has a good weight to it. Color is on-trend but classic enough to be a fave for a number of years. Paired it with blue jeans, black jeans, and leggings all for different looks and received many compliments. Love that it has side pockets — they could be a bit bigger though — but better than no pockets! Def recommend this as a fall and winter staple! I’m 5’5", 145lbs; ordered a medium and it fits the way I thought!" —Wendy M.
Get it from Amazon for $33.99 (available in sizes S–XXL and in 12 colors/styles).
2. A pair of breathable high-waisted leggings with moisture-wicking, fleece-lined material so that you stay warm and comfy when working out, running errands, or lounging at home — especially as the temps fall. They also have a hidden waistband pocket!
Promising review: "I bought this pair of leggings initially so I could have something warm and comfortable to wear while working at home that wasn't just a pair of sweatpants — they ended up becoming a staple of my workout wardrobe too! I ended up getting two more pairs in the no-pocket style so I can cycle through them during the week for my outdoor walks/runs. Fit-wise, if you're not looking for something super-snug, I'd suggest going a size up. The legs are a little long on me, but I'm short (5'1") and I'm used to things being a little long on me. My only gripe about these is that the side pocket isn't anywhere near big enough to hold my phone, but I've got a huge phone, so I'm used to it not fitting in pockets easily. Long story short: I love these, and if you're looking for warm leggings, either for working out or for lounging around the house, you should get a pair of these." —Beth Lynn Nolen
Get it from Amazon for $29.99+ (available in sizes XS–6XL, in 19 colors, and in two different pocket options).
3. Or a pair of reviewer-beloved The Gym People joggers, which have a tapered design and a stretchy waistband that'll probably make them one of the most reached-for pieces in your closet. And let's not forget the side pockets. 😍
Promising review: "I love these pants! I have several pairs and a few different colors. I wear them to the gym, errands, and for lounging. I have both mediums and larges, depending on how I'm feeling on the day. I honestly wear these so much that I consider them to be somewhat of a 'uniform,' a staple for a grab and go, cute but casual and put together outfit." —Pam
Get them from Amazon for $28.99 (available in sizes XS—XXL and in 16 colors).
4. A pair of adorable slouchy socks because they're the perfect accessory for an effortlessly comfy-yet-cute look. Plus, reviewers say they wash well and are super breathable!
Promising review: "These slouch socks are such a staple. I ONLY wear slouch socks. They are so comfortable, so durable and they are so cute! I love them so much I purchased another pack. These are my go to socks. And they feel like clouds! They're also true to color! They also go with ANYTHING!" —Chyna Mari
Get a three-pack from Amazon for $21 (available in five color variations).
5. A pair of thermal velvet leggings — get this, they combine the beauty of sheer tights with the comfort of warm leggings. Wear these fleece-lined babies under your dress or skirt and you'll be able to brave the cold weather without having to sacrifice a cute outfit. Plus, they're also available in non-translucent styles!
Promising review: "Super warm, good staple piece if you live in a colder climate. Ordered these for the winter thats coming, I live up north so I was looking for a good base layer to layer up. I love the sheer elastic around the ankles to tuck into my socks so they don't fall down in my boots." —Emery
Get them from Amazon for $20.99+ (available in sizes XS—XXL and in 10 colors and in multipacks).
6. A loose-fitting corduroy button-down shirt with button cuffs and a charming turn-down collar you can wear on your next coffee date for a relaxed, effortless look.
Promising review: "Staple for any outfit to layer or accessorize. Material is great quality, dress it up or down. I’ve worn this to the gym with leggings and sneakers and to brunch in booties with jeans, did not let me down!" —Melissa Garcia
Get it from Amazon for $35.98 (available in sizes S–XXL and in 41 colors).
7. A lightweight mesh-sleeve blouse — its elegant square neckline and puff sleeves will make it the new top you reach for when going somewhere that requires more effort than just throwing on a sweatshirt.
Promising reviews: "Nice lightweight shirt. Completely on-trend with slightly puffy sleeves, great weight, good quality fabric. A must-have staple." —Lily
"The fit is amazing. It looked super cute for date night. It was comfortable because of the stretchy body. And the sheer sleeves made the top look more fancy. I received several compliments!" —mmts
Get it from Amazon for $29.99 (available in sizes S–XXL and 25 colors and sleeve styles)
8. A reviewer-beloved Carhartt beanie that comes in a bunch of different colors, so you can add a stylish accessory to your outfit while keeping that noggin of yours toasty warm. Oh, and it has over 121,400 5-star ratings!
Promising review: "I own every color. It’s a staple. I’ve given this as a gift so many times I don’t know how many times I can review it. I’m obsessed with these hats. I own every single color and most of them I own in two." —Jasmine Young
Get it from Amazon for $12+ (available in 36 colors).
9. A pair of sherpa-lined sweatpants, which you'll probably end up getting in different colors because you'll hardly spend any time *not* wearing them. Now all you gotta do is sit back and sip on some hot cocoa as you commence your annual Christmas movie marathon and laugh at how utterly relatable the Grinch is.
Promising review: "It fits very well. I live in Seattle and these are amazing for the cold weather we're starting to get. I wear them in 35–55 degrees F weather and I can't feel any cold hitting my legs. I own them in pink and grey already. I'm about to buy them in black and navy. I truly think these are a staple if you want warm, cozy pants!" —Ash
Get them from Amazon for $38.99 (available in sizes XS–XXL and in 10 colors).
10. A moisture-wicking thermal set that is *perfect* for wearing underneath your clothes on your way to a snowy location, or as a comfy set of jammies! Its ultra soft fleece and heat retention will keep you nice and warm, and reviewers rave about how stretchy and breathable it is.
Promising review: "Purchased these as a base layer for our trip to Colorado. They definitely did the job as a good base layer. It was -17 degrees on our first day out in the mountain and these with an additional layer kept us cozy all day. These were a staple of our attire the whole trip. We did size up per recommended by others and it was accurate. So size up and just purchase!" —Ali
Get it from Amazon for $27.99 (available in sizes XS–3XL and in 15 colors).
11. A timeless Wrangler jean jacket because it goes with basically any outfit, and you can even throw it on over a hoodie for a bundled, layered look!
It's machine washable and has over 14,000 5-star ratings!
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 have been searching high and low for the perfect denim jacket. That search ended here! It's become a wardrobe staple for me, and I have to remind myself to limit how often I wear it because I want to wear it everyday! It stretches perfectly, it's warm without being hot, the pockets are perfectly sized and placed, I could go on and on! I love this jacket! It washes well, travels well, keeps its shape and keeps you warm!" —Alexa
Get it from Amazon for $39.99 (available in sizes XS–XL and eight colors).
12. Or a faux leather jacket to easily add a touch of classic coolness to any OOTD, even on those extra chilly nights! I'm pretty sure you could throw this on over a onesie and make it fashionable.
Promising review: "I have been trying so hard to find a duplicate faux leather jacket to replace the one I purchased from Forever 21 a few years ago. With that being said, I fell upon this baby right here on Amazon. I must say, I LOVE IT! Definitely a purchase I am satisfied with. I compared my measurements with the size chart provided and picked a size closer to my preferred fit and I just couldn't be happier with what I got. It's my STAPLE JACKET now." —LilRed
Get it from Amazon for $39.98 (available in sizes XS—XXL and in 20 colors).
13. A slouchy half-zip sweater with buttery soft material and a V-neck collar. Perfect for hopping on your Zoom meetings in something that isn't your pajamas but feels like pajamas (I guess looking semi-presentable is "important" — *rolls eyes*).
Promising reviews: "This sweater is good thick material and is a perfect staple for your wardrobe." —K Dramatic
"I LOVE THIS SWEATER! So soft and comfy but still polished looking! Perfect for my fall WFH wardrobe update. Works layered or on its own. I am going to get another color!" —SSK-LA
Get it from Amazon for $41.99 (available in sizes S–XL and in 21 colors).
14. A lightweight jumpsuit that you can dress up for a date night look that doesn't require wearing a dress that'll have you shivering the whole time. It has an elastic waist, keyhole back, and an elegant off-the-shoulder design to help you look effortlessly put-together.
Promising review: "Y'all. If heaven were a piece of clothing, it would be this jumpsuit. The fabric is so buttery soft and it is so cute and chic. You can easily dress it up with accent jewelry and some cute shoes, or nap in it. It has a cute boatneck cut, but if you leave the top keyhole unbuttoned you can achieve the hanging off the shoulder look. It is the perfect amount of 'baggy'. I probably could have ordered a small, but I am happy with the medium. Will definitely be re-ordering in other sizes. This is a new staple piece in my closet." —Rachel Landrum
Get it from Amazon for $37.99 (available in sizes S–3XL and 32 colors/patterns).
15. A chunky soft knit cardigan because it isn't winter without this classic staple. Throw it on over your leggings and T-shirt for a basic lounge fit, or wear it with your fave pair of jeans and a simple top! (And to all my fellow Swifties, you know what song to cue.)
Promising review: "Just as expected. If you want a baggier and oversized look I would recommend going up a size. I got a medium and it is just the right amount of oversize for me. The quality is nice as well, love my new black cardigan! It's a great staple piece." —Alexis A.
Get it from Amazon for $42.99 (available in sizes S–3XL and in 29 colors).
16. A simply chic and easy-to-accessorize mock-neck sweater that you can wear for both a casual or more polished look. Pair it with trouser for a day at the office or under a dress for a coffee day with your besties.
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 am so pleased with these sweaters. I normally wear a medium sweater, so I ordered the black, charcoal, and navy in medium and they are an instant staple in my wardrobe. They fit perfectly and go well with a pencil skirt or trousers for the office. 10/10 would recommend." —Lane Augustine
Get it from Amazon for $16+ (available in sizes XS–6X and in 17 colors).
17. A fan-favorite Orolay parka with over 20,000 5-star ratings that'll have you wondering how you've ever braved a winter without it. It's got a fleece-lined hood, six (!!) big pockets, it's windproof, and uhh...oh yeah, it's sooo cute!
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: "Is it really as amazing as everyone swears it is? Yes! This is warm and covers my perpetually cold butt without feeling like I can’t move like in my down jackets. It’s not bulky and I have plenty of room for sweaters underneath. This is a staple in my winter wardrobe as a mom of three always on the go and has gone back and forth between my closet and my college age sister's closet many times!" —Lacy B.
Get it from Amazon for $89.99+ (available in women's sizes XXS–5XL and in 13 colors).
Check our out Orolay down jacket review to learn more!
18. A long-sleeve tunic top if you just want to throw on a sweatshirt for your morning Starbucks run but don't want to look like you just rolled out of bed. This provides all the warmth and comfort of your fave sweatshirt, but looks so much chicer!
Promising reviews: "Lots of compliments. Everyone asks about this super cute top every time I wear it. I bought several and it's my staple winter top now." —Tiffany Taft
"Love love love this sweater! Warm enough without being bulky. I want one in every color! Color is true to pictures. No defects. Definitely a great staple. You will not be disappointed with this purchase!" —April
Get it from Amazon for $29.99+ (available in sizes S–XXL and in eight colors).
19. A pair of modish cargo pants that will take any casual look to the next level. They're cute, comfy, *and* have convenient front and side pockets? I'll take one in each color, please and thank you.
And just FYI, these are final sale!
Klassy Network is an Asian-American woman-owned small business based in Orlando, Florida that sells stylish clothing, including their TikTok viral Brami top (aka a top that provides amazing support and doesn't require a bra underneath!).
Promising review: "The cargos are perfect staple piece for my outfits! I get to wear a complete Klassy Network outfit, and it feels great. I am 5’2" and my pant size varies from size 6–8. I ordered a medium and it fits perfectly! I like the high-rise look, so I never got it hemmed, but I'm obsessed it’s perfect for when I want to wear heels and dress up." —Alexis T.
Get them from Klassy Network for $48.75 (originally $65; available in sizes XXS–3XL and in five colors).
20. A trendy cropped puffer vest to add both warmth *and* style for a casual OOTD. If you're not a huge fan of bulkier winter jackets, this'll keep ya cozy in the cold weather while still allowing you full range of motion.
Promising review: "New fall/winter staple. I am absolutely OBSESSED with this puffer vest. It is lightweight and not overbearing, but at the same time it keeps me warm and feels so comfy. I took the advice of other reviews and ordered an extra small even though I'm usually a small, and I'm so glad I did. I love the cropped look that the smaller size gives me. I will certainly be buying this in other colors." —Lydia Spencer
Get it from Amazon for $36.97 (available in sizes XS—XXL and in 20 colors).
21. A super versatile long-sleeve bodysuit with a square neckline, a snap closure, and endless styling possibilities. Style it with jeans and a pair of boots or with a long skirt and heels for more of a date night look!
It's also available with fleece-lined material and in a short-sleeved option!
Promising reviews: "This body suit is perfection. Comfortable and now a staple in my wardrobe for casual occasions, work, or even going out. It's versatile! Love it." —Amanda S.
"I'm usually not a bodysuit gal but these are so comfortable. The material is light but not cheap looking. There is plenty of room in the torso so it doesn't ride up like some bodysuits. It fits snugly but not too tight. They are great staple items for pants, jeans, skirts and shorts. I purchased three and will be buying more." —Jerr
Get it from Amazon for $26.99 (available in sizes XS–XXL and in 24 colors).
22. A buttery soft ribbed knit long sleeve because it isn't winter without this simplistic staple to keep you just warm enough without feeling too bulky during a lazy day in. Or wear it out — it's one of the easiest pieces to dress up or down!
Promising review: "I got this shirt in a large (I usually wear a medium) because I wanted to be able to wear it with leggings, but also have a little room in it. I have washed it, no shrinkage. I do hang it to dry just because I don’t want the colors to fade, which nothing has shown me in the washing process that it will. Just ordered my second one in a different color, great staple to my wardrobe and so grateful I have found this shirt." —Kirsten Fountain
Get it from Amazon for $21.97 (available in sizes S–XXL and in 26 colors).
23. An open-front knit cardigan with a stylish lapel neckline and two front pockets. It'll act as the perfect layer of warmth without clashing with your outfit for a night out on the town. The cold never bothered you anyway. 🤷♀️
FYI, this is included in Prime Try Before You Buy so you can give them a trial run if you're a member!
Promising reviews: "I bought this to go over some of my winter dresses. Love the color and it is so comfortable! It will be a staple in my closet now!" —Dana L Knight
"This is a classic, must-have wardrobe staple. Very well constructed. Beautiful weight and knit is smooth and soft. Holds its shape." —janice
Get it from Amazon for $49.99 (available in sizes S–XXL and in 24 colors).
24. A pullover striped sweater because sweater weather is officially upon us, baby! This soft knit piece is lightweight enough to feel breathable, while still giving cozy szn vibes.
25. A button-up oversized blazer — it just screams "chic." Pair it with a beret and some knee-high boots, and you'll look like you belong on the steps of the Met like you're on an episode of Gossip Girl.
Promising review: "You can absolutely never go wrong with a classic camel blazer, and this one is even trendier since it's slightly oversized. I still think it's fitted enough to be a wardrobe staple and not wane as trends fade away, though. I can dress it down with a cute crop top and some mom jeans, or dress for work with a cami top and some white slacks. It's such a versatile jacket and I'm pretty excited to style it a billion different ways this spring. The material is quite nice, too, and the lining will keep you pretty warm, especially in the shade or in the heavily air-conditioned office. Go ahead and take a chance on this one; it's been one of the best additions to my wardrobe this season and I foresee this piece serving me for lots of years to come :)" —Bibby928
Get it from Amazon for $37.50 (available in sizes S–L and in 17 colors).
26. A pair of palazzo pants that'll have you looking so chic and elegant, people would never guess that you're wearing your fave pair of fleece leggings underneath (shhh, it'll be our little secret🤫).
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 to wear for work, but 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! Highly recommend." —Skylar
Get it from Amazon for $33.99+ (available in standard sizes XS–2X, short sizes XS–XXL, and 31 styles).
27. An oversized cable knit sweater vest that you can wear as a mini dress with boots or with a long-sleeved blouse underneath. Either way, it'll look super chic!
Promising review: "A staple for my wardrobe. I bought this the first time in black, I loved the quality so much that I came back and bought the brown! If you’re looking for a quick, stylish fit this goes perfect with a collar shirt or turtle neck. I get lots of compliments and it’s so comfy! Highly recommend." —Monica Alvarenga
Get it from Amazon for $34.98 (available in sizes S–XXL and in 28 colors).
28. Or a trendy oversize sweater vest because it combines comfort and elegance. Wear it with a long-sleeved white button-up shirt underneath to achieve that sophisticated look with little effort.
29. A pair of moisture-repelling insulated bib overalls if you'll be having some fun in the snow this season. Reviewers rave about how warm and dry this keeps them in even the toughest weather. And don't worry, it's also super lightweight. So that you can glide down those slopes in comfort *and* style. 😉
Promising review: "Incredible staple piece for winter wear. This jumpsuit was amazing, kept me incredibly warm while snow tubing and boarding. They are waterproof and the cut makes my body look amazing. Great find!" —Zoraya
Get them from Amazon for $32.36+ (available in sizes XS–4X, in tall, short, and inseam styles, and in 28 colors).
30. A moisture-wicking long-sleeve sports bra to give your arms an extra layer of warmth if the dropping temps make you feel less motivated to get your workout sesh in. And bonus! It shows off those back muscles as you put in work at the gym.
Promising reviews: "Good quality and fit true to size. I love the material and this is a staple in my gymwear." —Hannah
"I’m OBSESSED with this top! I have a bigger chest and never thought I’d be able to wear something like this without a bra underneath but this top has great support and padding! I workout in this top comfortably and get so many compliments." —Lexie
Get it from Amazon for $26.99 (available in sizes XS–XL and in 23 styles, including some with short sleeves).
31. An A-line woolen midi skirt if you refuse to compromise style for comfort. With its classic plaid pattern and fully elastic waistband, this gives you both!
Promising review: "Heavy skirt for the colder months but light enough that I can wear in spring and fall, too. I absolutely love the pockets and am glad that the waist has a little stretch to it. So happy it is such a versatile wardrobe staple." —Blaze
Get it from Amazon for $36.99+ (available in sizes XS–3XL and in 60 styles).
The reviews for this post have been edited for length and clarity.