Staying Stylish All Winter Long

I grew up in the suburbs of Chicago and went to school in upstate New York. I spent a couple of years living in San Francisco before moving to Minnesota, but the majority of my life has been spent in parts of the U.S. that get Winters with a capital Wint. I’ve dealt with waist-high snow for 4 months solid, days that freeze the insides of your nose the moment you set foot outside, and wind chills of 70 below. (Really. No, really.) I’ve seen it all, and survived, and continued to love living in the Great White North.

But last winter almost beat me.

Last winter, it snowed a couple of feet in mid-November and that snow didn’t melt until May. Last winter, it was relatively mild and agreeable until February – meaning temperatures hovered around 20 or 30 degrees – and then there were six straight weeks of cold so brutal it literally made me weep in pain and frustration as I walked to and from class. Last winter was long and dark and relentless, and for the first time in my eight years of MN residence, I considered abandoning my beloved state for less trying climes. And last winter I gave up on style. I wore the same pair of black slacks every damn day, slicked my hair into a bun, and lived in myย Dansko oxfords.

BUT THIS WINTER I SHALL NOT YIELD! For one thing, I am not taking classes, so my cross-campus jaunts will be less frequent. For another, I finally got a parking space in the lot attached to my building, so I no longer have to walk 4 blocks of WIND TUNNEL from my car to my office. And finally, I just plain feel better equipped to stay stylin’ this time around. I’ve learned a lot, and I plan to apply it all.

Now, none of my tools or tricks are terribly creative or unusual, but since I had several folks ask how I’d be kickin’ it this winter, I’ll share. And, as always, I’d LOVE to hear how my resourceful readers plan to stay warm and stay hawt during the coldest months of the year.

1. Long-sleeved layering tees: ย I have amassed quite a collection. At the end of last winter I cleaned out a Target clearance rack full of brightly colored long-sleeved tees, and they’ve already been put to good use.

2. Tights: It’s amazing what a difference a thin layer of nylon can make if you’re sporting a skirt in a high wind. I don’t own a single pair of true fishnets, but am a huge fan of double-layers: A film of sheer black nylon beneath a fishnet = sexy AND warm. I have many pairs of thigh-highs as well, since actual tights reconfigure the mid-Sal, transforming me into a segmented worm. Hate that.

3. Lined wool skirts: Lined because wool sticks to tights, wool because it’s WARM! My beloved Boden makes a fantastic array of super heavy lined wool skirts, from minis to knee-length to floor-length. I typically buy at least one per year.

4. Tall boots: My ankles and toes get cold very easily when not encased in sock-and-closed-shoe. So although I intend to employ pumps occasionally, much of the winter will be spent clomping around town in my arsenal of knee-high boots.

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 not a 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 messily slung around my neck and shoulder area.

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. Load on the necklaces: When you’ve got exposed neck and collarbone during the warmer months, light, feminine jewelery is ideal. During the winter, though, when you’re likely to be wearing your necklaces over/atop cloth, going bold and chunky works best. Some of last year’s uninspired outfits would’ve been a thousand times more interesting if I’d just piled on some funky chains or slapped on a statement necklace. I plan to utilize every piece I own over the course of the next few months to keep my ensembles from looking blank and boring.

4. Follow the “color or bling” rule: By February of last year, my entire office was filled with women swathed in morose monochrome. This winter, I will attempt to wear at least one bright color EVERY DAMN DAY. If I am just unable to resist a black-white-gray outfit, I will apply trick number three with tremendous gusto.

5. Layer colorfully: I buy my layering tees a couple of sizes 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. Bright tights can add another pop of color.

6. Dresses as skirts: I have several sleeveless sheath dresses that I could relegate to basement storage … but instead, I plan to layer them. Long-sleeved layering tee, sheath 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!

Like I said, not exactly the world’s most innovative plan, but I think it’ll work. If any of you lovelies has other suggestions for cold weather chic, I’m all ears!

Snow image courtesy dawn_perry, all other images by me.

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  • kittyscreations

    Being a native Floridian who complains that it’s “freezing” when it gets below 50 degrees, this was a very enlightening post. Unfortunately, it never gets cold enough here for some of these tricks. Still, now I know how to not dress like the abdominal snowman whenever I go north ๐Ÿ™‚

  • Alison

    Cute hats can add a nice bit of warmth too. I am going to sort through my stash of long sleeved tees. I was going to get rid of them as many are too small, but layering them under everything is an awesome idea. I’m looking forward to your inspiring winter dressing outfits. I’ll see how long I can last with out using the cold as a cop-out. I already caved today… Ha! I’ll try again on Monday.

  • drwende

    I’m counting on you for guidance, as it’s been a while since I’ve regularly endured such splendidly Minnesotan moments as feeling the outer half-inch of my thighs turn to ice while I’m walking across campus.

    Layering is key, though, given that when it’s 10 below with a bitter wind, half the buildings will have the heat turned up to Sauna.

  • Dollface

    Awesome tips. I’ve always lived in Northern states so I am no stranger to cold weather.

    You mentioned my biggest “winter style” secret: tights! Seriously, instead of wearing pants all the time it feels so nice to wear tights and a dress (with lots of layering), and my comfy snow boots (NOT uggs). I feel feminine, but also very warm!

    My tip is to buy a very brightly colored coat. Since you’re wearing it every day, why not have something that pops out from all the black and grey? I love my green pea coat and always seem to get compliments on it.

  • Make Do Style

    Gosh you are up against the elements! The photo is lovely and yes keeping your neck warm is the key to it all!
    Uniqlo have just launched heat clothes to help in the cold – not any good for you at moment? (what with ban!)

  • Couture Allure Vintage Fashion

    Wintersilks also sells silk sock liners which are a must-have in my book. Slip on a pair of those lightweight babies under your regular socks and your feet will stay roasty-toasty all day. I’m also a big fan of scarves on cold days. As long as my neck and feet are warm, the rest of me is warm too.

  • pretty face

    I am very jealous of that fabulous boot collection which I spy!

  • La Belette Rouge

    I definitely sacrificed style for warmth when I was in Chicago. My first winter I tried to do chic. Year two I gave up and did warm. Both are possible. It is just a challenge and if anyone is up to it is lovely you.

  • Gladys

    Since this is my first winter in a real cold environment (Montana, I’m usuall in Southern California) I have armed myself with the cutest scarves from Ross and TJ Maxx. I also splurged and bought several pairs of knee high boots including a really cute pair of tall top cowboy boots. I also bought target out of layering “t’s”. I found a great deal on some vintage all wook fair isle sweaters and splurged on a really great fishermans sweater. Now if I can just figure out how to put them all together I think I’ll be warm and stylish. ๐Ÿ™‚

  • dapper kid

    Yikes not sure I could deal with your winters! In London the city pretty much comes to a standstill on a snow day lol. But wonderful adivice, I’ve been stocking up on thin colourful thermals for the colder months ๐Ÿ™‚

  • Hate This And I’ll Love You

    Knee high boots are my saviour right now. I have a pair of patent doc martens they are knee high and they are awesome for winter. Good for grip, so I don’t slip over in the leaves / on ice, but also sexy, as many males have commented on them. ๐Ÿ˜‰

  • Emily

    luckily we don’t get these kinds of days in socal, but it was really interesting to read. i’m so jealous of that great tights collection of yours!

  • K.Line

    Dear Comrade in Winter Misery: These are terrific suggestions – i’ve never thought of doing tights under fishnets but it’s genius. Last winter was a toughie for us all. I think (I pray) this year will be a little easier. Toasty plus stylish is a tall order – especially when you walk everywhere as I do. But I am slowly learning the tricks of the trade. A Canada Goose arctic grade parka is one of them.

  • Beth

    Thanks for this great post. Any tips on waterproof/thicker-soled boots that you can walk through the snow in, but that aren’t hideous? I normally wear a couple pairs of knee-high riding boots all winter, but when it snows here in Michigan, my feet are NOT happy! I would love any suggestions…btw, I do count Uggs etc in the “hideous” category.


  • Sharon Rose

    Hi there-fabulous post my dear!! My must haves include my thermal vest and long johns and I want to put my collection of scarves to good use too! Love the dress tip too, such a great idea! Have a lovely weekend!

  • April

    Ah I hate winters in upstate new york! I remember my friend showing up to school in a miniskirt one winter day, with no tights mind you, and we were like WHAT ARE YOU WEARING, and she goes, “IT’S TWENTY DEGREES OUTSIDE. ITS WARM!” And actually, in the winter, 20 degrees IS warm. ish.

    I’m envious of your boot collection! And I plan on stocking up on pashminas in every color and pattern when I go to NYC in a couple weeks!

  • Audi

    Don’t forget that you can layer skirts too! A longer skirt poking out under the hem of a shorter one is both stylish and extra warm. I do not miss those Minnesota winters one bit.

  • hollarback

    Where did you go to school? I lived all over upstate in NY when I was little. I remember coming back from a trip to visit family in April (Easter break) and our house was completely snowed in – we had to dig our way in. That was when we were up by the border. Yes – feet of snow in April – living in upstate NY means you have a shovel in the trunk of your car at all times.

    I now live in Southern California (for work reasons – I don’t like the weather actually) My blood has thinned a bit, but I still laugh when people wear gloves when it’s 60 degrees.

  • Skye

    This is such interesting stuff to read for me, living in the land of perpetual sunshine (except for the hot, steamy wet season that we’re in right now).

    I love little sneaky peeks into life in other parts of the world!

  • enc

    I love this post. It makes me feel all warm and fuzzy. I bet you’ll have a lot of fun with your winter wardrobe this year, with your new ideas and circumstances. And parking space! ๐Ÿ˜€

  • a cat of impossible colour

    When we moved here from Zimbabwe, the cold completely undid me. I slept in two sweaters, gloves, a woolly hat and socks on top of my pyjamas. It was awful. I have adjusted somewhat, but am not a cold weather animal – I would love to live in a warm climate again!

    I have to say, though, winter dressing is lots of fun. ๐Ÿ˜€ Back in Zim I used to watch episodes of the Gilmore Girls and wish I lived somewhere with ‘proper’ seasons where I could wear scarves and woolly hats. So I really can’t complain.

    (But I will!) ๐Ÿ˜›

  • airstreamdiva

    Here’s a different sort of problem to ponder in your off-hours: I live in Houston where it gets into the 40s maybe 20 times per year. Period. The rest of the time it is muggy and hot. Emphasis on muggy.

    If I was a waifish type I would revel in spaghetti strap sundresses all the live-long day, but this is not the case. In fact I am rather curvy and the top part of my arms have not seen the light of day for well over ten years. Thoughts on staying stylish for the full-figured gal in the tropics?

  • Sarah Von

    Ahh! So helpful! This is exactly the information I needed. A girl needs to learn how to take her southern hemisphere wardrobe a bit north.

  • miss cavendish

    I used to skate to university when I lived in Ottawa and the canal would be a wind tunnel every morning. Imagine skating with a satchel slung across your body, expending considerable energy, yet not seeming to move forward. I’d layer like crazy, and I also had a long, insulated, waxed cotton, enormous Hilary Radley coat for the top. For my head and neck I’d wrap a beautiful paisley wool square around my ears, wind another scarf around my neck, add earmuffs and a beret on top. Not sleek, but perhaps, if you squinted, oddly eccentricly engaging? Maybe?

  • Songy

    I’d better revisit this when it gets colder here in say July.

    You’re well organised, Sal. I’m impressed.

  • The Seeker

    Oh I love this post, so helpfull, and I love that you’ve focused the wear of colour ๐Ÿ˜‰
    Why be gray when winter is sometimes gray? (Not that I don’t like the b+w look, sometimes I love it)

    Great tips darling, I think you should write a book with guidences.

    Have a gorgeous weekend.

  • ebinbaby

    Hey Sal,
    I’m located NORTH of you in Canada where the temperature regularily hits -40C (which is also -40F) for 3 month of the year! I often wear skirts and dresses to work with tights but find that it is too cold to have any potential knee/thigh exposure between knee-high winter boot and giant down-filled coat. Rather than wearing a full set of bulky pants underneath my outfit to prevent frozen knees, my secret is to yank up a pair of wool legwarmers up my legs to “bridge the gap”. The bottom of the legwarmer can either fit in or go overtop of the boots and they stay in place for the pubic transit ride and walk home.
    Love your advice – layers are the way to go. I’m definitely going to use your tights + fishnets method this winter – thanks!!

  • Mrs. Makeover

    I believe snot starts to freeze in your nose when the temperatures hit about 4 degrees above zero. Maybe a little cooler. The first time it happened to me was a big “WTF?!” moment!

    Scarves really are amazing. Such a small piece of fabric can really do the trick!

    I need to get some wicking socks, as my feet sometimes get sweaty and then that makes them feel extra cold. Other than that, I’m pretty much ready for winter.

  • The Penny-Pinching Princess

    I’m a firm believer of #2. I put a cami under EVERYTHING! I don’t care what the material is. It’s especially helpful under wool to keep you from getting all itchy.

  • lisa

    Great post! I already do a lot of these things (except the silk long-johns…it doesn’t get THAT cold in Vancity). And I couldn’t agree more with how necessary long-sleeved layering tees and tights are! We’ll both be toasty during the cold snaps lol.

  • Robyn

    Awesome post! I feel that most advice on dressing for winter is not made for Michigan. But I know Minnesotans know what’s up.

    I also heard Land’s End is good for silk long johns.

    My problem is finding nice boots with good grip also (for walking on ice and snow).

    And I also had an orange coat I got a lot of compliments on.

    It seems like v-neck/scoopneck tops are nice for winter too… like that’s all the skin you can really show…

  • Kat

    I'm way late to the game here, but awesome tutorial on cold-weather style. Where was this post when I moved to MN? By my second winter I'd figured out a lot of these tricks…but painful trial-and-error. Besides the proper coat, La Canadienne boots changed my world. Totally waterproof, great traction, still classy enough to wear with a skirt while teaching.

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