Winter Style Tips: Warm Fashion for Cold Weather

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Many of you have written to me lately on how to handle very cold temperatures while maintaining your personal style. While it’s frigid right now by DC standards, I don’t deal with such cold temps on a regular basis and would never consider myself to be an expert on cold weather fashion. I know many of you live in far colder parts of the country and world than I and would love you to weigh in on what you swear by to stay warm and fashionable. Below are the winter style tips I use to stay warm when it’s super cold:

cold weather fashion how to stay stylish and warm tips

Have a Base Layer

Keeping your core warm will ensure you stay comfortable when the temps drop. Thin layers close to the body will do a remarkably good job without adding too much bulk to your outfit.

  • Fleece and wool tights are my jam; I’ll wear a regular pair of tights under for extra wind and cold protection, and have even worn them under jeans and work trousers.
  • The same holds true for fleece and wool leggings. Check athletic departments and brands for great ones; while some may have reflective strips others will be solid black which will fit perfectly into your work or weekend wardrobe.
  • Wool socks keep your feet warm and dry and also help prevent foot odor. The chunky cable or marled versions are back in style and look cute peeking out of ankle booties or tall socks so they add style with warmth.
  • A silk or heat-keeping fitted tank or cami is a must-have in winter. Brands like Lands’ End carry these in a broad range of sizes and colors so you can find one to fit and become invisible under your clothing.

Wear Smart Accessories

When it comes to accessorizing in the winter, choose pieces that have fashion as well as function. It’s possible for your styling accents to keep you toasty in the winter.

  • I’m such a fan of pashminas. In wool, cashmere, or a blend these scarves are toasty without being bulky, stylish, and versatile. I will cross a pashmina across my body in front before putting on my coat; it will fill the neck area but also add an additional layer of warmth to my core. Once at my destination I’ll loop it around my throat for a pop of color to my outfit. Pashminas are also great when it’s not freezing; they can act as a shawl with a dress and I take them on travel to be my plane blanket as well as to ward off strong A/C on planes and at conferences.
  • A cashmere beanie is in style right now, so it’s easy to find a color and weight that appeals to you. I have a black cashmere beanie that I’ll put on in the morning and not take off until I go to bed. I style my hair around it, intensify my lip color and it’s a chic look that also keeps me warm. Adding a hat when it’s cold can really do much for increasing comfort; in fact I am writing this while wearing my cashmere beanie and am quite comfortable even though it’s around 60 degrees inside.
  • Gloves are a must-have and my favorite are cashmere-lined leather gloves. They are super warm, wind repellent, keep you dry when scraping off your windshield and look quite chic. Right now is the perfect time of year to stock up on leather gloves as they are on sale everywhere after the holidays. I always have a pair of classic black but when I can find fun colors like purple or green on clearance I snatch them up so add a pop of color or fun to black outerwear.

You Need Proper Footwear

When it comes to inclement weather, function always trumps fashion. A pair of warm boots that provide traction on slick sidewalks is a must-have for cold weather. Come winter, I keep a pair of black pumps at the office and wear boots on my commute. When out and about, slim jeans and pants look great peeking out of tall fur-trimmed winter boots for ski lodge style. Tall leather boots (especially if they are waterproof) are wonderful for when it’s cold but there’s no snow or ice; the leather is a wind breaker and an extra layer of warmth. I’ll wear tall  boots with a dress or skirt, fleece tights and wool knee-high socks and be toasty while still maintaining my personal style.  FYI all the boots featured in the carousel below are waterproof and ready for all sorts of frightful weather!


Choose Outfits with Layers, Length, and Warm Fabrics

If you plan on getting away with a long-sleeved tee and a pair of jeans you’re going to be shivering all day.

  • Layer: I’m a fan of sweater coats, puffer vests, and ponchos come winter because these are easy layers to slip on and off depending on how high the heat is cranking inside. Under, I’ll wear a long-sleeved tee or fitted merino or cashmere sweater and a silk tank under that so when I slip off the topper I am still pulled together and warm. Chunky knits are popular this fall and easy to layer over a silk or knit tee. I’m also known to slip fleece tights or silk longjohns under dress pants or jeans come winter and no one is the wiser except my warm self!
  • Length: Winter isn’t the time for mini skirts and crop tops. I pull out the midi skirts and wear with fleece tights and tall boots, longer tunic sweaters over slim pants or sweater dresses over fleece or wool leggings and tights, and thigh-skimming sweater coats keep my rear and upper legs warm.
  • Warm Fabrics: Wool pants are truly warmer than synthetics; look for a pair with lining to stay itchy-free and add some wind repellant. As mentioned a thousand times already, fleece and wool tights and leggings are a smart choice with dresses and skirts. Leather is wind repellant and warm; I wear a lot of leather skirts come winter for fashion with function. This year sweater and sweatshirt dresses are on trend and look great with tall boots and leggings or thick tights.

Longer Coats that Repel Wind

Many years ago I wrote that women don’t need puffer coats and can be just as warm and more stylish with a wool coat with Thinsulate lining. And now that I commute in a city, ride public transportation in the snow, and walk longer distances I agree with many of you who thought my advice bunk. Buy a coat that keeps you warm. When it comes to frigid temperatures, first look for something that will keep you as warm and dry as possible, then look for stylish touches. A quilted or puffer coat with a longer length is brilliant because it’s wind and water repellant, will keep your bum warm when sitting at the bus stop, prevents gusts from slipping up inside the coat, and is often machine washable. I like styles that at least cover the rear and have a belt which keeps you from looking like the Michelin man. While I wear a hat almost always, a hood is an additionally nice feature when you’re waiting for the train or it begins to drizzle. Buy from a company that is known for outerwear and get one that is made for the climate you experience. Companies like Patagonia, Lands’ End and LL Bean often give temperature ratings for their outerwear helping you make the best coat decision for your lifestyle.


And now I pass it back to you, what are your tips for staying toasty when the temperature drops? What are the best items in your wardrobe for winter weather? What brands or items do you recommend to those who are trying to stay stylish in the cold? Thanks!


A woman with curly hair wearing a plaid blazer holds a green fur coat over her shoulder on a city street.

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  1. Skinny jeans or cords just don’t cut it during the winter time here in the Pacific Northwest. I wear skirts or dresses most of the winter time and I have learned the concept of being comfortable yet warm and stylish at the same time. I buy a lot of the cuddl duds and have even worn on on top of the other as they are lightweight yet are loose enough to wear on top of the other – this is when it gets below 30 degrees outside and our office isn’t warm enough. On top of that I have my go to tights – usually black with plush fleece or just fleece covered from the top to the end of my toes. I’ve tried pairing on two of these tights on top of the other but I almost lost circulation in my feet when driving so a fair warning – don’t do this! On top of that I put on a pair of the thick fleece Cuddl duds leggings that are loose enough to slip over my tights. I try to wear the thin cuddl duds in black underneath everything as the white colored ones kind of show through my black fleece tights.
    I also went to Nordstrom rack to pick up a pair of my first sweater tights in mohair and polyester. I go up a size so I can wear what I can fit underneath. If I wear this and my tights and thin cuddl duds I’m set. Either the mohair tights as the last layer or the thick fleece cuddl duds over my tights and stuff are both pretty warm and toasty. If you’re able to pair another pair of the warm mohair tights over another one, you’ll really be warm.
    As for the top in cold, cold weather, I put on my thin cuddl duds crew neck long sleeved long john, then my thick fleece cuddl duds long sleeved top/fitted crew neck sweater on top. Then I put on a very comfortable and looser crew neck sweater, boucle or any other warm yet light weight sweaters on top to cover the layering underneath as well as added warmth if needed. If not, I find very loose tunics do the job to give the look some style. Add a warm scarf. I have lots of chunky old navy scarves that I wrap around to finish the look. Depending on the length of the sweater, I might add a skirt or not if the tunic or sweater is long enough. Because I am wearing so much layering on the bottom it’s thick enough that people assume I’m wearing thick leggings thus I don’t care if my tunic is a little shorter. I pair it with flat short or higher boots to the knees but usually flat soles. I might also find a long dress shirt that is loose enough for my warm layering underneath and long enough to cover my tights or leggings underneath then put on a shorter sweater on top to complete the look.

  2. I agree with Mrs. M……nothing is warmer than fur. I’ve only tried sheepskin, but I assume other furs have the same insulating properties. I have a knee length sheepskin coat that I could wear naked in the worst below zero weather and still really really not be cold. Its that good. (It is unfortunately, quite heavy).

    Excellent article and tips from commenters, I’ve enjoyed reading very much!

  3. This post makes me smile, because I remember when you were saying that a wool coat was plenty – and I was shaking my head and thinking you were out of your mind. I was in New York then, and I relocated back to the midwest in the last few years – and last winter was a major kick in the pants. In New York I could actually get by with a wool coat and no snow boots, but in Chicago? I thought I was going to die last winter, and the first thing I did this year was by snow boots.

    At least I remembered to get a parka when I moved back home.

  4. All of these are solid picks, but I would also suggest checking out Uniqlo. It’s a Japanese company slowly making its way into the US market- I believe the only stores are in New York and California. However, they do ship, and their long underwear is to die for. I also have one of their down coats (like this-|/women/outerwear/down/coats/| ) and it is also very warm.

    As for footwear, I have to use insoles, but Santana Canada makes some nice boots, and I believe La Canadienne does too.

    Also, people don’t bring it up because it’s controversial, but fur keeps you warmer than pretty much anything else.
    (References: New Yorker; lived in Ukraine for 2 years.)

    1. Agree, the Uniqlo Heattech range is amazing! Their down gilets are good too as they are warm without being too bulky.

  5. Timely subject matter. I enjoy wearing a variety of winter outerwear depending upon the temperature. I’ll wear a nice wool dress coat for dressier occasions. I currently own Ann Taylor woolen overcoats in black, brown and tweed from seasons gone by. I love wearing fleece jackets that can be layered with down vests for my days of being on construction projects. Lastly, I have several lengths of down coats for the type of weather we’re currently experiencing here in the NYC area. My new go-to accessory is (are?) The North Face e-tip gloves so that I don’t have to take them off while talking or texting on my cell phone.

  6. I have a toughie. My mother (she’s 87) and because of irritation, only wears skirts but no tights. She lives in WV & her legs get cold. I actually cut sleeves out of a cashmere sweater & she uses them as leggings, but I just wondered if anyone had a better idea? I haven’t found any thigh-hi (or over the knee) socks that will stay up – any thoughts there? To top it off, she does not do synthetics, so cotton or wool blend is a for sure. Grazie!

    1. Leg warmers? I get mine from dancewear supply stores. They come in all length s. Also, try sockkdreams or Vermont country store or for wool and cotton thigh highs.

        1. Yep, ballerinas often wear full length super insulated leg warmers to keep their muscles warm before rehearsals so dance wear shops (or look online) should be able to help your mama out 🙂

  7. Great suggestions! I was wondering if you had any ideas for coats/jackets to wear over maxi skirts? I’ve never worn one in the winter but it seems like it would be pretty warm to layer long underwear/tights/leggings under a maxi skirt or dress, but I would be at a loss how to pick a coat silhouette to wear over it. Short coat to show off the length? Long coat to echo the long skirt length?

    1. Hi Hayley! I’ve lived in Boston (and now New York) for the past five years and I actually find that maxi skirts and dresses are a hassle in the winter because they get all gunky and gross at the bottom from the mud and snow. For the few black-tie events in the winter that call for ball gowns, though, I like to wear a wool coat that ends a little past my knee. I think shorter coats look strange over the long skirt since it cuts you into two columns of fabric, although if it’s not bitterly cold, I love the look of a short fur (real or faux) coat and a longer dress on the bottom, which works especially well if the fur is heavier and chunkier and the skirt silhouette is more clingy. Hope that helps!

    2. Like Nancy, I’ve had trouble with maxi skirts in winter because they can get all mucky on the bottom. I have one jersey/sweatshirt-like maxi but don’t wear it often because of this reason, and also it ends up clinging to tights and getting caught on boots. When I do wear it, I choose a shorter fur chubby or my below-knee chinchilla that has an a-line shape so it doesn’t compete as much with the length.

      1. This brings up a good point about dressing up in the winter – tips for winter weddings, the opera, all that. I am always shocked by the number of fancy winter dresses that don’t have sleeves! And don’t even get me started on shoe options. Sigh. These looks all work great for work (and they are much appreciated!!) but another edition for fancy things would be lovely.

  8. I wear dresses/tunics pretty much exclusively, and this is my system:
    Base layer – underwear and bra, then fleece-lined black leggings and a tank top. The leggings look just like opaque tights but are much more comfortable.
    Clothes – dress/tunic, cardigan, scarf.
    Feet – Tall leather boots, and super thick chenille socks.
    Outer layer – heavy knee-length coat with hood, gloves.
    ETA: the best part is, I come home, take off all the layers except for the undies, tank, leggings and socks, throw on a hoodie, and I am comfortable and warm for lounging and sleeping! I don’t even wear pajamas, I just sleep in the tank and the leggings. 🙂

  9. I learned to embrace what I call “LLBean lumberjack formal” in winter here in Nebraska. I worked in a business casual environment (university PR) my entire career and we are practical and pragmatic regarding dressing for the weather. In fact, folks who dress more for fashion rather than weather realities are kind of not taken seriously here. If you are wearing 4 inch heels on ice with bare legs when it’s -22 windchill, folks question your common sense. I am a huge fan of fleeced leggings (and I’ve not found much quality difference between $24 Hue and 2 for $15 Walgreens brand, so I go cheap on these). I prefer skirts, even in winter, and have several wool pencil skirts from Bean that I wear with my leggings, and woolen socks with boots or ankle booties. I love the leggings in fun colors, too, like red, cobalt or yellow. I love a thin silk tee or polypro running shirt under a regular shirt, then cashmere or wool sweater or blazer. And a puffer from Lands End, with hat, mittens and infinity scarf. Yeah, it’s lumberjack, but I kind of rock the look and it’s super comfy. My biggest winter problem is static flyaway hair but a tiny amount of the coconut water conditioner you recommended gently smoothed over hair reduces that a lot.

    Also, remember thin layers with air between (so not sausage tight) offer much more warmth.

  10. I hate Target clothing but love their accessories. Their stockings are the only stockings I will buy, and I have quite a few scarves from there. A few months ago I noticed Target carries sweater tights, and those are the only things I will wear when it’s cold. I work downtown and like to walk on my lunch break, and a few days this week we’ve had a wind chill of 5 to 10 below during my lunch, so it’s been cold. I wear my Target sweater tights, knee-high leather boots, a knee-length wool coat with a hood, a Target scarf wrapped around my head and face, and fleece mittens. Fleece isn’t a great wind barrier, but my hands heat up enough when I’m walking that fleece is just perfect. Under the wool coat I wear a skirt, a shirt, and a cardigan.

    After reading your post, I am ready to do some shopping for a new pair of boats or some more wool.

  11. Embrace the puffer coat! Having had commutes that have included standing on windy train platforms and walking several block during Chicago winters I don’t think I would have survived without one. I cannot encourage enough getting one that comes at least to the top of your knees or longer, it makes all the difference. I have owned a North Face Metropolis Down Parka for years and it has held up great. One of the best features is the hood. While not stylish when it’s up it keeps me warmer than any hat could and has the added bonus of not messing my hair up, which is a hard task in the middle of winter!

    Also I found a stylish sweater coat to keep at the office. It’s an extra layer to throw on when I get chilly sitting at my desk but doesn’t look so frumpy that if our company president stops by announced I don’t feel too casual.

    I think the best thing is that those of us who live in colder climates have reinvented what stylish means for us for the coldest of months. When temperatures started to drop and it was time to break out boots all the women in my office were excited to show off what they would be wearing for the winter. Sure, we all might look a little silly to someone in LA but dressing for cold weather can be fun too! When else do you feel empowered to stomp around in brightly colored, faux fur lined boots while sporting a pom pom hat?

  12. I agree that it’s easier to layer with a skirt than with pants. I have a Smartwool miniskirt that I’ll use as a slip in really cold weather. On a trip to New York last year, I picked up a fleece-lined quilted nylon wrap skirt at Uniqlo, and wear it as outerwear over skirts or pants.

  13. Thank you for this post!!!! I am a native Texan, but often vacation off-season in colder climes for budget reasons, including my recent honeymoon in Boston. I always struggle at figuring out how to stay warm, and as a result am slowly developing a vacation specific wardrobe for when we’re on our trips. I will be pinning this one for sure! I’m also so glad to have you back from the holiday break, I missed my WO fix the last couple of weeks. 🙂

  14. Silk long underwear saves me on the coldest days, and the tops are usually elegant enough to be visible if you take your top layer off (just wear a vest or cami as they tend to be see through!)

    Layer, Layer, Layer. Right now I am wearing fleece lined tights with wool thigh highs over them, and my Uggs. Wool and silk are my go-tos for cold weather. I’m looking for a shoe version of Uggs so I don’t have to wear them all day (I hate cold feet)

    Don’t wear your coat indoors- you’ll acclimate too much to the indoor temperature, and then you will be even colder outside!

    Fingerless gloves are very helpful in a cold office, and covering your head with a scarf or chic indoor hat helps alot.

    Mittens are much better at preventing frostbite than gloves. Sometimes I’ll wear my leather gloves inside of my mittens for extra warmth. I’m lusting after some sheepskin mittens.

    Skirts are often warmer than pants. A wool or leather skirt layered with a slip, fleece or wool tights and warm boots keeps me much warmer than a pair of jeans.

    Embrace dirty hair. I normally wash my hip length hair every day and let it air dry, but in winter I’ll go 3 or 4 days between washing. Another reason to embrace hats and scarves!

    Put some vaseline on your hands before you put your gloves on.

    Pashminas are my jam. I wear mine as a scarf outside, then as a shawl as needed indoors.

    Cover your face outside. It is hard on your body to breathe cold air- a face mask or scarf will warm the air before it hits your lungs.

    And of course, warm drinks, hand warmers, etc…

  15. any recommendations for good, true-to-size fleece tights? i bought 2 pairs online that should have been more than large enough (by both the height and weight chart), yet i cant get them above my knees!

    1. I got ones from Orablu (sp) they were at Bare Necessities and Nordstrom but are now sold out. But they are the first pair I have found that truly fits well and keeps their shape. I did link to a few other brands available at Bare Necessities in the carousel but honestly don’t know if they’re any better than the awful ones I got last year on Amazon.

    2. I always size up on them, and I have found the footless ones fit much better than the footed ones. I haven’t found much difference in quality between the $6 ones and the $30 ones.

      1. Yup, I’m always comfier in tights (fleece or otherwise) if I size up. I’m much rather a touch of sagging that being pinched around the waist (but mostly they don’t even sag).

        I don’t have that much experience with really cold weather, but I do second what you’ve been saying, Allie.

        It was bloody freezing in Belgium on my recent holiday so I put on a thermal vest, tights under my jeans, kneehigh boots, a bit cashmere pashmina and a hat that covered my ears. My coat wasn’t quite warm enough, but it’s fine for English temps.

        1. It was before Christmas, so they may not be there any more… but they were on hangers on a carousel near the active wear, not on the shelves near the bags where the tights in packaging would be, if you know what I mean. 🙂 Good luck!

  16. I love this! I find it so challenging to stay warm and comfortable and mobile in a lab environment during the winter. I have to wear all shirts at bracelet length for safety and wearing gloves, and scarves don’t work, either (they get in the way when you’re working at a lab bench).

    I find that wearing doubles of tights is hard, but doing one pair of tights and then a pair of leggings can work. This is a much harder thing to pull off if you’re not wearing boots. I like fleece leggings, but I find they pill pretty seriously after a certain point, and graduate into “only under pants” and away from skirt territory.

    I really enjoy the look of Sorels, but walking in them any longer than half a mile really hurts the top of my feet – any thoughts?

    1. I was fleece tights and leggings inside-out on the gentle cycle and line dry, that keeps them from pilling so quickly. I can do fleece tights on top because they’re not so tight, but could never do two pairs of normal tights, it’s so awkward and I end up spending half the day in the bathroom trying to get them back up!

      As for Sorels I had the same exact problem except for the Joan of Arctic wedge ones I have. My winter boots are from Lands’ End who may not be as “cool” but have a far roomier footbed and I can walk a mile in them without issue.

      1. Oh my gosh that’s exactly the problem I have with two bottom layers! Fleece on top of regular tights has been much better than other leggings (though, if it’s cold and you need to wear a skirt/dress and look somewhat nice, you can do the matching tights and leggings from Silkies…there’s still a line where the leggings end but it’s not super noticeable).

        I didn’t know the inside-out trick, I always line dry, but maybe that will help with pilling.

        Joan of Arctic wedges or Lands End got it. I always feel like the footbed isn’t well described online. It’d be so helpful for people with a higher instep! I’ve been thinking about a pair of Steger Mukluks as well, they have a softer moosehide layer, so you don’t have the same hard plastic problem that you have with Sorels.

        1. My mom has a high instep and has a heck of a time finding boots. I know she wears the classic LL Bean Duck boots, but she has also had the same pair for over a decade so I have no idea if they’re still shaped in the same manner.

  17. Thank you so much Allie for these tips! I was among those who was writing to you about being stylish in rough weather 🙂
    I can add that warm woolen or fleece shorts save me in the coldest times of the year. Sometimes tights are just not enough to keep warm and protect from ice-cold wind, especially if l wear a skirt. And we, girls, need extra protection from abdominal problems the cold may cause.

  18. Wisconsin reader here! Something to remember in extra cold temps is to up your moisturizer game. Have a thicker, soothing cream for the mornings before you put on your makeup. It makes all the difference!

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