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1. A pair of fleece-lined joggers that'll feel like someone sewed your favorite blanket to the inside of your favorite sweatpants. The silhouette means that if you're so inclined to wear these on some errands, you can still look a bit put-together.
Promising review: "10000000/5 stars!!!!!! I just shoveled our driveway for an hour in 2-degree weather and my legs NEVER got cold. While my hands, face, feet, and arms were cold...legs were nice and toasty. I am recommending these to everyone!!!" —jc
Get it from Amazon for $24.99+ (available in sizes XS–XXL and five colors).
2. Some fleece-lined leggings to keep you feeling toasty when you're forced to leave your house.
Promising review: "Wow it took serious willpower not to buy a bunch more of these leggings! They're so perfect if it weren't for the fact that I hate winter I would say I can't wait to wear these! They are so, so, so, so soft and fluffy inside. It feels like you're wearing the best kind of leg blankets ever." —sierrahasCat
Get them from Amazon for $18.99 (also available in 14 other styles) or get some plus-size leggings for $29.99 (available in four colors).
3. A cozy leopard-sleeve sweater can easily distract from your (essential) snow boots that you don't love while keeping ya' nice and toasty.
FYI, this sweater is included in Prime Wardrobe so you can give it a trial run if you're a member!
Promising review: "SUCH a cool sweater! Great quality, awesome print, got a lot of compliments!" —Amazon Customer
Get it from Amazon for $33.99+ (available in sizes S–XL and in 14 colors).
4. A quilted Vera Bradley tote in weather-repellent, durable, lightweight performance fabric so you don't have to worry about getting caught in the rain and getting everything in your bag wet.
Promising review: "You’d be hard-pressed to find something negative to say about this bag. I use mine as a crossbody and it’s a wonderful size. It’s not huge, but definitely big enough to carry everything I need. The front magnetic pocket is great for putting small items that I use often like my keys or masks while the back slip pocket is perfect for my phone. And you can’t go wrong with performance twill. By far it is my favorite fabric from Vera Bradley. Easily wipeable and no worries if I get caught in the rain. It’s such a wonderful bag to have in various colors." —Amy
Get it from Amazon for $110 (available in nine colors and prints).
5. A pair of sleek touchscreen-friendly gloves with rubber grippers on the palms so you can keep your paws on your phone. *And* these'll match basically any cold-weather outerwear.
My colleague Emma Lord uses these when she's running outdoors in NYC winters. So, uh, they're legit:
"I've been using these all winter to run outdoors, and they're also just supremely warm and soft. I've had trouble finding decent running gloves to keep my hands from getting cold without overheating them for years, and these are the first ones that are so functional that I barely even think about them when they're on (which is saying something, because I am a very picky bean about my gear)."
Get it from Amazon for $11.99+ (available in sizes M–XL and five colors).
6. A matching sweat set that'll help you fight against chilly gusts of will-it-or-won't-it-snow while looking cute.
Promising review: "Got this set to sleep in for the winter. The material is very comfortable and soft on the skin and not irritating at all. The stitches were flawless and looks exactly like the picture. I actually wore the sweats outside with another top and I was feeling fine the whole day." —Kesha Follz
Get it from Amazon for $35.99+ (available in women's sizes S–XL and five colors).
7. A cute crossbody bag you can feel OK about taking on every single last errand because sometimes winter weather hits REAL fast when you're not anywhere close to home and you've got your really nice bag on you.
Promising review: "I had been searching for this size bag for a while, it's not too big, but large enough to fit my essentials (wallet, phone, glasses case). I can even fit a medium size book in there :) The quality is awesome as well. Perfect crossbody bag for me." —Amanda Hubard
Get it from Amazon for $23.95 (available in 28 colors).
8. Water-repellent ankle boots that'll still scream fashion while you *safely* stroll down the wet-snowy sidewalk on their sturdy rubber soles. AND they're from Naturalizer so they're super comfy despite the bit of height. I should know. I own them and wear them ALL the time!
These have been my go-to fall and winter ankle boots for the past year or so. They're super comfy, look a bit goth (my own personal preference), and can withstand all sorts of rain and wet snow. I wore them about a month ago to dinner on a night where it was snowing and coming down fast, quickly accumulating on the sidewalk in powdered layers. I wore these and managed to get home fine while walking a bit slowly, despite seeing a guy in front of me EAT IT on the sidewalk. That was a night where I should've worn proper snow boots but I was fine to walk the eight NYC blocks home in these in the pouring down snow. Oh, and did I mention that they're total compliment-bait? Well, they are.
Get them from Nordstrom for $180 (available in sizes 7.5–11; also available in matte black).
9. And a set of heat-retaining socks can help keep your lil' piggies toasty down to -15 degrees F.
Promising review: "These socks have just changed my life. I am not even kidding. I suffer all of the time from feet that are painfully cold when the temperature outside is anything less than about 75 degrees F. It is horrible. I wear double socks with slippers; still have cold feet. Always having them tucked under a few thick blankets while watching TV, etc., but still feeling the cold in my feet. Well, I saw the reviews and ordered these. I put them on this evening, put on my usual slippers, and shortly after I felt like I had an electric heater inside my socks. They feel so very warm and toasty. I have never had a sock that could do this. Even thick wool socks don’t do this. MY FEET ARE ACTUALLY WARM which is something that rarely ever happens. I am in LOVE with these socks. I could kiss whoever invented them." —Linda Marie Nutter
Get a three-pack of women's sizes from Amazon for $24.99+ (available in sizes 5–9 and 8–13 and two color sets) and men's sizes for $24.99+ (available in sizes 7–12 and 12–15 and two color sets).
10. A thermal top with ties in the front to help ya' build a cute outfit that's warm but not too warm. I guess it would be a little weird to wear your thermal underwear to the mall. This is a nice compromise.
11. A pair of spiky ice and snow grips can make you feel (nearly) unstoppable once you clip them onto your winter boots. Each grip has 19 stainless-steel spikes to help you get a better footing and the harness just slips over your boot. Yeah it might rain, but it could also full-out snow. It's good to have these in your car.
Promising review: "I used these on a backpacking trip to the Grand Canyon. The top of the rim was very icy for several miles and these literally saved my life. No joke. If I didn’t have these I would've been stuck at the bottom 'til the ice melted. Great price and great product. And easy to put on and take off." —Megan Depper
Get it from Amazon for $17.99+ (available in unisex sizes S–XXL and three colors).
12. A cozy eco fleece sweatshirt ready to replace that old stained one you've been using for layering for years on years on years. Or at least you can wear this one out in public and the stained one *just* in the house, k?
Promising review: "Purchased this same sweatshirt for my husband YEARS ago which alone says something about its durability. He wears it continually as we are in a cold climate. He decided to actually purchase the same product to where while the first one was in the wash. It's being made a bit longer now which is fine and I like his so much I decided to get one just like it for myself... both happy campers. 👵🏻👴🏻" —P. Flynn
Get it from Amazon for $32.67+ (available in seven colors and men's sizes S–3XL).
13. L.L.Bean Boots will be in for the long haul through lots of flighty weather forecasts and can be resoled at a store location!!!
Promising review: "My husband has the same boots and he's worn them for 10 years so far. Just took them back to Bean to have them resoled (so they can last another 10 years!). That convinced me to buy myself a pair, wore them through a hurricane and several rainy days so far, and I've only had them for two weeks. They are waterproof and comfortable, I have no problem wearing them all day. Much better than my Hunter rain boots." —hannabean
Get them from L.L.Bean: women's for $139 (seven color combos, sizes 6–11, three widths) and men's for $129 (two color combos, sizes 7–14, three widths).
14. A lightweight water-resistant down coat as a topper against the chill that'll pack down to fit in a small bag. Affordable, available in eight colors, and easy to transport? Sign me up!
FYI, if you have Amazon Prime Wardrobe you can give this a spin before you buy it!
Promising review: "I loveeeeeee. Super lightweight and warm!! Worth the purchase, and I love that you can fold it up into a small pouch for easier travel. This jacket is a little long as well but Amazon sells a normal length version as well." —mayacoston
Get it from Amazon for $23.13+ (available in sizes XS–XXL and eight colors).
15. A clear crossbody handbag can weather the, well, weather. I have this bag and have carried it to so many places where I *might* get wet.
Clearly Handbags is a small biz founded by Kori Green and Ro Rynd to help solve the problem of finding stylish handbags that still pass clear bag requirements for stadiums, sporting events, concerts, and other events that require them.
This is my Clearly Handbag that I snagged at a boutique in Nashville in October. I've used it at least a dozen times since then, including to go out on the town that very night on a bachelorette, on rides (including Splash Mountain) at Disneyland, and just while I bar hop with friends here in NYC. It's large enough to hold the stuff that I need for the night (and even a very small book to read on the subway if I plan accordingly). I get tons of compliments on it because, like the founders of the company say in their "about" statement, there are so few actually cute clear handbag options. I love that this has a purse strap I can change out (yes, they sell cute straps) if I so choose, and that the studs on it make it feel like more of a statement. I've been caught in the drizzle in this a few times and it's been fine...unlike if I was caught outdoors carrying a suede bag.
Get it from Clearly Handbags for $65 (also available with brown, red, blue, and purple zipper details).
16. A hair finishing cream on a mascara-like wand for helping slick back those baby hairs and flyaways that tend to really come out to play whenever there's even 1% chance of precipitation in the forecast.
Promising review: "No matter what I do or what expensive and high-rated product I try, my fly-aways are an annoying constant. This product has completely rid me of my daily top of head fly-away frizz! I wish I would have discovered this product years ago! It smoothes my hair out and truly lasts all day. Be careful, as a tiny bit goes a long way!" —RHoffsommer
Get it from Amazon for $7.98.
17. A windproof umbrella with a sunny outlook — even if that's the complete opposite of how you woke up feeling to the pitter patter of rain.
Promising review: "So big and pretty and really built well. I love how it catches the rain when collapsing. I bought two. One for me and one for mom." —leigh nelson
Get it from Amazon for $18.88 (available in 16 styles).
18. A pair of sneaker-style rain boots in both hi- and low-top options you'll come to rely on for those days when it's a 30% chance of rain and you 100% don't want to ruin your good suede ankle boots OR sweat it out through wellies. Plus! If it doesn't end up raining, it's NBD.
Promising review: "I bought these for an event, when the weather report kept saying it was going to rain the whole time. Rain boots would have been great, because the mud was DEEP, but at the end of the day, the shoes never got stuck in the mud, and my socks were dry. They are also super cute, which is a bonus. Everyone thought I was crazy and just wearing regular shoes :)." —SarahJoy
Get them from Amazon for $25.99+ (available in 17 colors/styles and women's sizes 6–11).
20. Or some weather-centric hair claws you'll wanna sport when it's super sunny out, too.
Matt Live Supplies is a small biz specializing in a range of cute hair claw and clip designs.
Get it from Matt Live Supplies on Etsy for $8.07 (available in cloud or lightning styles).
21. A houndstooth sweater vest to help you take advantage of sweater weather without imprisoning your arms. This'll be especially handy in case it ends up just raining and is weirdly 15 degrees warmer than expected.
Promising review: "I’ve been looking for this kind of sweater vest forever and I finally found the one. I’m very happy with this purchase. The quality is great and the fabric is very thick and heavy. It might sit a little large on me so I would probably exchange for a smaller size. Great for fall/winter. I would recommend pairing it with a white button-down for a chic look." —Jane T.
Get it from Amazon for $25.99+ (available in sizes S–L and in 18 colors).
22. A super-pretty puff-sleeve minidress I just bought in green that you can easily wear with tights and snow or rain boots in messy weather without worrying about your hem getting wet.
Promising review: "It’s super cute, comfortable, and I received a ton of compliments on it. I ordered a medium but could have gone with a small. Ordering another color, because I liked it so much." —Amber Nelson
Get it from Amazon for $35.99 (available in sizes S–XXL and in 10 colors).