Cold Weather Dressing Essentials


dressing for cold weather

We’re digging in for the long winter haul here in MN, so I figured it was about time to revisit my personal list of cold weather dressing essentials. Now, none of my tools or tricks are terribly unusual, but since I’ve had several folks ask how I’d be kickin’ it this winter, I’ll share.


  1. Layering tees: I have amassed quite a collection of layering-specific tees and tanks over the years. Why are they reserved for this use? Because I have bought them tight enough to slide beneath other layers – including close-fitting sweaters and blazers – which means they’re not quite loose enough to be worn on their own. If you want to layer without lumps, your underlayers need to be pretty durned tight.
  2. Tights: My picks for the best warm tights can be found right here, and I stand by them. I’ve since invested in another pair of Falke opaques and absolutely adore them. If you are a skirt lover, a relatively dressy dresser, and live in a cold clime, I highly recommend investing in at least one pair of high-quality tights to see if they make a difference in terms of comfort and warmth.
  3. Lined wool skirts: Lined because wool sticks to tights, wool because it’s WARM! Boden makes a fantastic array of super heavy lined wool skirts, from minis to knee-length to floor-length. Talbots also tends to line their skirts. Many of my best lined wool skirts have been thrifted. (Naturally some skirts will be unlined. Invest in a slip!)
  4. Tall boots: My ankles and toes get cold very easily when not encased in sock-and-closed-shoe. So although I employ pumps on warmer days, much of the winter will be spent clomping around town in my arsenal of knee-high boots. I know tall boots can be tough, so here’s a post with specialty size resources. Also see Wardrobe Oxygen’s post about online retailers who specialize in wide-calf boot styles.
  5. Scarves and wraps: I had an evaluation with an acupuncturist once and she told me two things that I have never forgotten. One is that the bizarre, embarrassingly loud single hiccups that I get on occasion are the result of “rebellious chi.” The other is that, if I want to stay warm, I need to keep my neck covered. I believe them both. Since I am no fan of actual turtlenecks, this means that I employ a lot of scarves and wraps. Fashion scarves get creatively tied, and provide a surprising amount of warmth despite being constructed from flimsy fabrics. Wraps, pashminas, and mufflers get slung around my neck and shoulder area. (Fave large scarf tie here.)
  6. Silk long johns: Silk, as you likely know, is nature’s miracle fabric. Keeps ya cool in the summer, and toasty in the winter. I’ve had my silk long underwear since high school and it has saved me from losing my pelvis, thighs, and calves to frostbite more times than I care to count. Silk is also sleek and won’t bulk up your pants. Wintersilks will be happy to sell you a pair.


  1. Wear tall boots under slacks: Keeps calves extra warm, and no one is the wiser! I have several fun pairs of ankle boots that will be in heavy rotation, too, but on those snot-freezing days, fortified lower legs can make a world of difference.
  2. Wear a nude cami under everything: When it’s really horrible outside, I’ll throw on my nude cami, one of my long-sleeved layering tees, and a sweater. Three layers, minimal bulk.
  3. Layer colorfully: As I mentioned above, I buy my layering tees a size too small to minimize lumpage, and make sure they’re nice and long. That way, I can throw them on beneath non-cardigan sweaters (crews, v’s, and cowls) and let a little contrasting color peek out at the hem and sleeves. Bright tights can add another pop of color. So can scarves.
  4. Wear dresses as skirts: I have several sleeveless dresses that I could relegate to basement storage … but instead, I plan to layer them. Long-sleeved layering tee, dress, cowlneck sweater. The bottom half of the dress peeks out from beneath the sweater and just looks like a skirt, but I’ve got an extra layer up top!
  5. Don’t forget accessories: This has nothing to do with keeping warm, but I cannot resist throwing it in. When it’s cold and dark and you have to put on upwards of seven separate garments to keep yourself from freezing, the mere thought of adding jewelry or a belt may cause a minor tantrum. But most outfits benefit from those finishing touches. Try to remember to add earrings, a watch, a brooch, or a barrette. You’ll look and feel more pulled-together.

Like I said, not exactly the world’s most innovative plan, but I think it’ll work. Hope these suggestions are helpful!

**Disclosure: Actions you take from the hyperlinks within this blog post may yield commissions for See Already Pretty’s disclosure statement for more details.

Originally posted 2012-12-05 06:11:41.

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43 Responses to “Cold Weather Dressing Essentials”

  1. Elly

    Everything you ever needed to know about cold weather dressing in one place – thank you Sally!

    I’ve rediscovered my (vast) collection of scarves this season and really enjoy playing with their patterns and colours. Plus, I’ve added a few wraps and larger, woolen scarves to the mix – including a retro British Airways blanket that is perfect for cuddling up to/over/under/around.


  2. Stephanie

    Where I live, it doesn’t get that cold for very long, but in the winter months, I try to keep a jacket in the car (in case I get down to the car in the morning and realize it’s colder than I realized)! 🙂

  3. Emma Hill

    The other ‘trick’ I’ve passed on is to tuck my inner top layer into my inner bottom layer in to create a sort of sealed under layer. I get chilled easily and I nearly always wear a cami as a vest and then tuck it in, into my tights if I’m wearing a dress, into my trousers or skirt if I’m not. Can’t bear it if my kidney area gets cold.

    I used to volunteer at a local seaman’s centre and frequently had to tutor new Filipino merchant sailors on how to cope with northern weather. Introducing them to vests and then getting them to tuck the vests into their trousers was always an uphill stuggle. “Ma’am, Filiponos wear things loose”, but it makes such a difference.

  4. Bree Bronson

    Hi Sal!

    I live in Finland (Europe), and it gets *really* cold in here. I’m talking about temperatures down to -25 C and even below. Today we’re down to -15 C. So it’s just terribly cold, and most people rely on skiing clothes or something that looks very much like it. They’re warm and practical, but I hate to look like a skier for 6 months in a row. I adore pretty clothes, and dressing for winter has always been a problem for me. I’m allergic to wool which makes finding fantastic winter clothes and accessories even harder.

    Would you have any tips or ideas for North Pole (ok not really, but the Arctic Circle does cross Finland) residents? How to look classy when h*ll freezes over?

    Judging from people’s outfits most of us up here have actually given up – so I’d be ever grateful for advice! Thank you!

    • Sal

      Oh my gosh, Bree! I have the very thing for you! My friend and colleague who goes by The Waves is from Finland, and moved back recently … AND she just posted about dressing for the Finnish winter!

      We do get subzero days here in MN, too, and I’ll admit that for the most part, I give up on looking truly chic under those conditions. I’m most likely to do a large scarf, cami, long-sleeved tee, cowlneck sweater or sweater coat, silk longjohns, tall boots, and jeans.

      Overall I’d say find as many silk garments as you can, and layer them up. Make sure your base layer is silk for sure, and track down some large silk scarves for accessorization. Can you do cashmere? It’s a great cold weather fiber and can layer well.

      General tips:

      1. Play with pattern mixes. (Tips here: If you’re getting bored and can’t vary your staple garments much, doing print mixes can keep things interesting.

      2. Printed scarves. When it’s that cold, keeping your neck covered will be ESSENTIAL. Even if the rest of your outfit is plain, a fabulous printed scarf will jazz it up. My favorite scarf is actually extremely thin cotton, but it’s so huge that by the time I’ve wound it around my neck it’s very warm.

      3. Consider hats. Are you a hat person? Ski hats can be pretty plain or sporty, but if you knit or can find some artisans on Etsy who make more eye-catching ones, you can add that accessory to you mix and be warm and stylish! Go for silk/cotton blends.

      4. Be mindful of color. Even sporty clothes can be fun if they’re colorful! Opt for brights or jewel tones instead of relying too heavily on blacks and grays.

      Hope that helps, my dear!

    • Viktoria

      I´m in Swedish Lapland and I have pretty much no particular winter clothing any more – but I am the queen of layering! The only thing I add is hat, gloves, warm shoes, and a pair of zip-off themo pants. This year, I have explored layering summer/autumn coats and jackets, instead of taking out a bulky down parka that is mostly too hot anyway, except if you are standing still for hours outdoors. It works brilliantly. And, everything Sally says, I second.

    • Jenny- Adventures Along the Way

      In Quebec it is usually well below 0 C during winter, and it gets down to -20 C (and sometimes below that, especially if you consider windchill when talking about the temperature).

      I don’t come from a cold climate originally, but my most essential things to feel warm are:
      -good quality, warm boots. I have these and absolutely love them: (And I have a different pair of warm winter snow boots that I wear for less extreme winter days. Cute leather boots are relegated to indoor wear only once the snow hits (from about December through April), but I carry them with me and switch when I get to work, or I keep them at work and change into them.
      -a warm hat (I have a wool one that is lined in fleece) that covers my ears snugly.
      -mittens (which are ski mittens actually). I learned after experiencing winter here that mittens kept my hands significantly warmer.
      -a warm double-layered fleece scarf
      -a warm coat (which I left off my list at first because it felt obvious)

      Obviously these are all things that are sprty looking, but they get removed once you are inside. As far as the clothes that get worm underneath, I find that “normal” winter clothes are generally okay if I have good winter “outer” gear. I find regular leggings and jeans are fine (and I don’t wear long underwear underneath), even on very cold days. I do often use Sally’s trick of multiple top layers, including a base tank top, a long sleeve shirt and then a warm (but not too bulky) sweater.
      And this winter on some -15 C days so far, I’ve started layering legwarmers over leggings above my boots, like tall “boot socks” like Sally mentioned in a post the other day. I’ve liked the extra warmth. Unfortunately many legwarmers are too small to do this.

      If it is a very cold day (colder than -20 C maybe) I might add my snow pants on top of my jeans or skirt-and-leggings outfit, and that keeps me toasty while only looking ski-like while walking to work or wherever. When it’s so cold that my eyelashes are frozen together, I decide that warmth is the important thing. 🙂

    • Bree Bronson

      Ladies, thank you *so much* for your tips and ideas! I had time to go through them properly just now. They didn’t only give me ideas but also motivated me to look for something nice for the winter!

      I’ll absolutely invest in silk and scarfs. Also, I’ve been uncomfortable with layers (I feel kinda stuffed) but now I’m starting to realize that I probably should consider a bigger jacket! Longjohns is a bit problematic I think because at least in here it’s really warm inside and if I’m shopping for example I really get hot.

      But once again thank you, you’re super awesome!

  5. Patti @ NotDeadYet Style

    If it *ever* cools off here, I really love wearing tights and boots, with a well-fitted jacket and over-sized scarf. Please, how about a few days in the 60’s?? Love your full skirt with those awesome platform pumps.

  6. Jen

    I have to echo your scarf sentiment as spot on. The last two winters our young son was suffering from bout after bout of strep throat and various other throat-related illnesses. When I would take him to our family practitioner, I was dressed in my cold weather uniform-which includes a vast array of scarves. She has commented on this often, telling me that by keeping the throat warm, it helps warm the entire body and help your body fight off illness. Now, I still get ill a few times each winter (I work in a school and have a elementary aged child) but I think there is wisdom to the use of scarves. I am warmer when I wear them. And when I do take to my bed feeling under the weather, I will pull my softest and lightest scarf off the hook and wrap myself up-even if I’m wearing sweats and surrounded by tissue. Only then it isn’t a fashion statement!

  7. Debby

    I live in New England and am *always* chilled until about May. Your tips are perfect!

    After years of brushing off my elders’ warning to wear a hat to keep my head warm, I finally caved. I found a pretty magenta cloche in a little boutique in Cape Cod last year that is warm and doesn’t smoosh my hair down (and then make it static-y when I take the hat off). Those knitted headbands that cover the ears but keep the back of the head/hair open are also pretty and practical.

    I also like fingerless gloves for when my hands are frozen indoors but I need to do things, and I have a big black ruana (like a pashmina, only wider and with thicker fabric) that I carry with me everywhere. It’s as warm as a blanket, only more stylish, when I just can’t get rid of the chill. 🙂

  8. Asher

    There is a lovely move not to use “nude” as a color–or not to use it without calling attention to the way it creates what gets to be “normal” when it comes to skin tone. (The calling-attention approach can be syntactically unwieldy, but I welcome that because that very awkwardness helps to convey, clearly but pleasantly, the intent NOT to participate in the implications of the naming of “nude.”

  9. Dee

    Sal, any reason you left off hats, gloves and other outerwear accessories? I am guessing because you were not addressing outerwear per say. But I find that if I wear too many heavy/warm layers under my coat I get hot at the office too easily. What works for me here in Chicago is a good down coat, with a hood, and yes, a warm scarf or turtleneck (or both!) for the neck. I think we all know that we lose much of our body heat through our head. If my neck, hands and head are warm I can even deal with a not so heavy coat or bottom layer. I guess we all figure out what works for our own body thermostat!

    • Sal

      Yep, I figure everyone has her own outerwear-related cold weather preferences, but wanted to focus here on indoor/everyday clothing! And although I think some environments are accepting, many – including most offices – still frown upon wearing hats indoors. (Not all! But many.)

      And yes, all of this is subject to your internal thermostat and daily environment. Some offices are unbearably warm in winter. I’ve worked in many that skewed hot in cold weather!

  10. Jasmine

    Thanks for this post. I may have to start layering more again after my 30-30 Challenge is done. And thanks for linking back to the pretzel scarf tie. I will be using that today!!

  11. Cecelia

    Sal, can you (or anyone else) recommend good skirts that block the wind? I find leggings/tights/longjohns under a skirt to actually be warmer than pants, at least until that wind starts up.

    I second silk longjohns! I’m working on finding a silk slip for layering, too!

    • Sal

      Have you tried maxi skirts, Cecelia? I’ve found that I can layer a thrifted silk maxi under a jersey/knit one, then longjohns, then boots. SO WARM.

      Otherwise, I find lined wool to be the best at blocking wind. Preferably a thick, borderline boiled wool.

      Anyone else have suggestions?

      • Cecelia

        I LOVE maxi skirts, I just haven’t found any good winter ones, all mine are super summery cotton gypsy skirts…

  12. GlamaRuth

    Uniqlo Heat Tech. End of story. Tights, leggings, camis, short and long sleeve Ts – and Uniqlo just opened up online. Obviates the need for multiple layers. And they don’t get stinky.

  13. Becky

    I’m a Texan girl who moved to Northern New England six years ago. The first four winters were appalling and wretched, but I’ve adapted and here are the things I have learned:
    – Everyone has their own winter-wardrobe needs! I created my first my winter wardrobe by copying my dear MIL, who always looks beautiful and has lived here all her life. But what was comfortable for her does not work for me.
    So the rest of this list is what I have learned for myself:
    – Wool is magic. I sweat a lot, even when I’m cold (nice, right?), and wool is warm and stink-free even when it’s damp. Wool socks are the best, and I splurged on a pair of fabulous I/O Bio brand merino wool long john bottoms – I find them 100% non-itchy. They rock as baselayers and and PJs too.
    – Designated “baselayer” tops are not very useful except for outdoor sports. Even then, once you get inside you’re going to want to strip down to your baselayer, so it ought to look OK as a single layer and not be see-through. Better to use tees and camis as your innermost layer up top; many long-john tops have high necks that stick out of clothing.
    – 2-3 light, thin layers are more comfortable than a bulky sweater. You’re less likely to overheat & sweat, leading to the damp chillies later. Bulky cable-knit sweaters look so cozy and lovely in the catalogs, but ’round about March you will be *dying* not to wear 10 lbs of clothing anymore.
    – Keep your feet warm and dry at all costs! I live in the boondocks, and NEOS (New England OverShoes) are great for popping over my street shoes/boots and plowing through the snow to the car and digging the car out. I can then take them off, drive to my destination in street shoes, then put them back on if my destination is also a snowy wasteland. My feet have never been cold in these things. Also, I have an outhouse, and the NEOS are great to throw over slippers for a quick trip outside. Dog-walkers and mail-fetchers would also love them.
    – Shawls are warmer than sweaters when you are sitting still indoors, because your body can keep your arms warm. And they’re quick on/off; I tend to need one more layer sitting still than I do moving around in the kitchen etc., so shawls are most practical at home.
    – Fingerless mittens are great for computer work, reading, etc. Warmer and more comfortable than fingerless gloves.
    – I broke down and chose a hairstyle based on the need to wear hats much of the time, including to bed. Getting a big wardrobe of super cute winter hats of varying degrees of warmness made this less sad than it might otherwise have been. Another reason to get lots of winter hats – I have lost many, and people have left many at my house whose owners I have never ID’d. Don’t get too attached.
    – I discovered that my thrifty Southern minimalist wardrobe habits just do not work for the *wide* range of winter temperatures (indoor and outdoor) that obtains in New England. I have many more articles of clothing now, and I spend more on clothes. A single day can go from 50 F indoors in the morning to -30 F outdoors to 80 F indoors by a friend’s wood stove. This requires attention to layering and unlayering all day long.
    – Many winter garments require hand washing (wool, silk, knits). It helped to embrace frequent hand-washing rather than let it pile up in a fusty mound of shame. I bought some lovely fancy soap (Eucalan grapefruit scent) and made a habit of hand-washing every few days. Created a designated drying space so things drying don’t feel like clutter. A fresh, fluffy clean winter hat or silk cami is a little joy; stale, grimy warmies make mid-March *even* more depressing.
    – Snowshoes are a mental health tool!

    • Marie

      I am exactly the same about the need to layer and unlayer! I often wear a light “fashion scarf” indoors, which I sometimes pull over my shoulders, when I get cold from sitting/not moving. For going outside I will often put my woolen scarf over top. – Putting on a hat, than the hood(s) and the scarf around as the outermost layer keeps the strongest winds out : )

      The layering also works for gloves – I have some cheap one-size-fits-all ones, which I wear with fingerless gloves over top in the morning and then only the fingerless ones on my way home. Or I put thicker pleather ones over top. – That also helps with drying time. – Nothing more disgusting than having to put on wet gloves.

  14. Laurel

    Leather is great in the winter. It blocks wind and isn’t bulky. I have a suede midi-length skirt that I love wearing with tall socks and/or boots.

  15. Kayla

    Sal, A trick I learned from you several years ago was to wear double tights. Sometimes I will wear spanx nylons under tights to minimize bulk.

  16. KL

    Sal–where do you find fitted but longer-length layering tees? I am petite with short arms but a long torso, and I haven’t been able to find layering tees that are both fitted enough not to look lumpy and also my ideal length for easy tucking. For instance, J.Crew’s perfect-fit crewneck tee is fitted enough for layering in XXS and for regular wear in XS (but the sleeves are a tad long and wide, tending to scrunch), but the length is not long enough to tuck into my low-rise jeans.

    • Sal

      Hmmm, so interesting to hear this, KL, as I find that most layering tees are MILES too long for me! I buy a lot of Bella brand for layering, and they label some items as “longer length” They’re designated as “great for layering or low-rise bottoms” and “features a longer body length and slim fit.” Could work!

      I’ve found that Old Navy and Target both cut long for my proportions, but I’d bet you’ve checked there already. Bella stuff is cheap via Amazon, so might be worth a try.

      • KL

        Thanks Sal! I haven’t tried Old Navy and Target in recent years, so I’ll give them another look. I did try Gap’s highly-rated crewneck tee in XS, and the length was good but the body wasn’t fitted enough to be a true layering tee. And I keep hearing about Bella tees, so I’ll give them a whirl if other options don’t work out.

  17. trefoil

    I do circuit court 3-4 days a week in the northern prairies, and need to be warm AND professional. When it hits -40, I wear a tank top tucked into silk long johns tucked into cotton socks covered in wool socks, long sleeved wool t-shirt, dress pants, wool sweater, knee-high boots, scarf and blazer. It’s surprisingly not cool, and the wool layers mean it’s not super-bulky.

  18. Angela

    GlamaRuth, thank you for chiming in with your comment about Uniqlo’s Heattech line. I’ve heard good things about it, but since they only just recently launched their e-commerce site, I haven’t been able to try it yet. Something about never having seen their clothes in person makes me nervous about figuring out what size I am in their line, particularly given that I’ll have to pay their $7 return fee to send back anything that doesn’t fit.

    I’ve been firmly in the SmartWool base layer camp for 5+ years. Is it time to revisit silk? I haven’t tried a silk base layer since my “conversion” to SmartWool, but I seem to recall not thinking it was all that warm.

  19. Sonja

    Just another thing that nobody has mentioned yet, although it might be a neglectable factor: It gets really warm underneath a broad, obi-style belt. I learned this the hard way last summer, but it’s an advantage on colder days!

  20. Zadi

    Holy buckets… you get random embarrassingly loud single hiccups too? I tend to joke that I’ve had the same case of the hiccups for the last decade, with a delta of around 24 hours between ’em.

    Now I need to go research ‘rebellious chi’…

    Thanks so much for these tips, though. I do tend to employ a lot of these during winter, though only this year figured out the tight undershirt thing. It allows me to still wear some of my nice short-sleeved work tops into winter, if I’ve got multiple layers underneath. Can’t believe I hadn’t thought of that before. Also, I definitely need to expand my collection of tights.

    Oh, one more tip: hats! My hat collection really shines in winter because it’s not too hot for something on my head, and as a bonus they help keep warm. Bucket hats, trilbys, even sun hats can work wonders for warmth retention.

    My feet are pretty much always cold, so in winter I often wind up wearing tights + two pairs of socks + boots, but then my darn feet will sweat like you wouldn’t believe all day regardless of the temperature, resulting in wet and cold socks. Any tips? Do I just need to give in and switch to an all-wool sock collection?

  21. Annette

    Sal your tips and tricks are right on. I live in Alaska where winter is both long and cold. Although southeast Alaska is not as cold, we seldom see temperatures below -15F it is damper which is just as chilly try 30F with humidity of 90% and you will swear it is much colder.
    Back to clothing — layers is a must, I wear silk long johns and camisoles then a t-shirt or blouse and then either a wool sweater, cardigan, or polar fleece. I top this off with a warm coat. Yes to scarves too. As someone else mentioned smartwool socks and sweaters are great. For those in the US and Canada REI has a great selection of smartwool.
    My husband works in various villages across western Alaska and 2 things he always wears is a fur hat and gloves and gortex pants lined with polar fleece.
    If you sew there are lots of products that can be used including wool, thinsulate, gortex or other rain proof products that layered together are nice and warm.

  22. Ann Cox

    I was so glad to see this post – it’s freezing here in London Town at the moment, and I’d been worried I didn’t have enough warm clothes. Love the idea of transforming dresses into skirts – had a look through my array of Spring/Autumn jersey dresses today and worked out which jumpers and thick tights would work with each of them. I feel like I’ve just doubled my winter wardrobe without having to buy a single thing!!

  23. Julie

    I can also vouch for Uniqlo’s heattech line. They are made to be fitted but they are light and stretchy and move with your body (order your true size, but be aware they’re more fitted than the regular Ts). The long sleeve top I just ordered is so slinky and comfortable, it feels like you’re wearing nothing and it’s ideal for layering. The size charts on their website are actually specific to individual items and very accurate in my experience. Anyway, I just love it–and SO affordable.

  24. Lina

    This winter season, I bought a new shape wear cami for layering under tops. Since it’s shape wear, it’s tight and it’ll add minimal lumps/bulges 🙂

    I also have a pair of glove liners made out of silk. I can wear them at the office if my fingers get cold while typing, or they can be worn as intended, as liners underneath regular gloves.

    Finally, I have a pair of ear muffs. Usually, when my ears are warm, then most of my head feels warm… weird, I know. I prefer ear muffs over head bands and hats because they won’t mess up my hair do.

  25. Jennifer

    Belated thank you for the bit of inspiration about wearing summer dresses as skirts! I just snagged a gorgeous summer-weight dress on clearance, and was bummed about having to wait to wear it. Until I remembered your advice! Today I’m wearing it with a long sleeve T underneath, and awesome fleece-lined purple tights (thank you also for your general tights inspiration, and also your recent post on how to wear tights).
    I guess, thank you in general for inspiring me to find and wear clothes that make me feel pretty. I do feel pretty today!

  26. Jennifer

    I got so many compliments for my outfit today! Not that I do it for the compliments, but they are sure nice to hear!