Winter Dressing From the Ground Up

Winter dressing is on my mind today, my friends. This is not surprising since, with the advent of five or six inches of snow that has fallen in the Ottawa area and not gone away, fall fashion and sweater weather are done like dinner. And winter layering is here for the foreseeable.

I adore sweater weather. Every year I am excited to wear my sweaters and blazers, jeans, shoes with socks, and scarves. I can sally forth in the morning knowing that aside from unwinding a scarf when I sit down to lunch, my outfit can remain intact the whole day. Indoors and out. So easy.

But sadly, sweater weather is a very short season. It’s sandwiched between early fall when it’s still too warm to wear a light sweater under a blazer, and late fall-early winter when it’s too cold to wear a blazer or heavy sweater as outerwear. I completely missed sweater weather this year. Except for the week between arriving home from Portugal and falling ill with the dreaded virus. And the ironic thing is I spent most of that week lolling around my sunroom, reading, and dreaming what I would wear now that we were home and sweater weather had arrived. Ah well, as Inspector Thursday always says in Endeavour, one of my favourite television dramas, “mustn’t grumble.” There’s always next fall.

Winter dressing so I blend in with my surroundings.

Don’t get me wrong. I love the snow. Especially the first snowfall. What I don’t love is all the palaver and fuss of winter outdoor clothing. And all the layers which one must pile on before proceeding outdoors, and then remove immediately when one comes back inside. Coats, scarves, gloves or mitts, hats and toques, boots. And that’s just the extra outerwear required. Long underwear is a whole other topic.

Unlike sweater weather, winter dressing requires the planning of an outdoors outfit and an indoors outfit. Unless one is participating in an entirely outdoor activity like skiing or walking, one needs to think about being warm enough when outside, but not too warm when inside. And don’t get me started on the boots conundrum.

Indoor mall shopping is the very worst winter activity for outfit planning. It’s the combination of cold outside and overheated inside. Once at the mall, warm outdoor scarves have to be unwound, coats unbuttoned, and then eventually removed completely to avoid heat stroke. Unless you are lucky enough to find a coat check, and are able to divest yourself of your outside outfit, you must lug your coat, bag, and scarf, plus parcels around until you either finish your shopping or give up in exhaustion.

I have such fond memories of winter shopping at Holt Renfrew when my friend Liz was the personal shopper there. I’d drop my coat and outdoor scarf off with Liz, and browse happily, unencumbered. Those were the days, people.

In fact, aside from shopping at Holts, I hated winter mall shopping until I bought my Uniqlo ultra-light down jacket. That jacket is the perfect mall shopping piece. It looks great, is light as a feather, and if I must take it off, it can be easily stuffed in a purse or shopping bag.

Now these are real-life winter outfits.

This time of year, at the very beginning of winter when I haven’t yet adjusted to dressing for the colder temperatures and the snow, I’m always looking for winter dressing inspiration. Real life outfits, or at least outfits that can be translated into real life. Real winter life. I find much of my inspiration on Pinterest, although it’s hard to find outfits to pin that are actual winter outfits. I have better luck with certain Instagram accounts like the one above. The girls in the photo are wearing outdoor boots, and mittens, and even a hat. There is snow. And their outfits are simple, minimalist, chic… and warm enough to wear during winter. They give me ideas for what to wear from my own winter closet.

And I need ideas. I have to come up with a few decent outfits for parties and get-togethers which I will be attending in the next three weeks. Post-Covid-cough-willing, that is. I want my outfits to be smart enough to look as if I am making an effort, but not fancy, and comfortable enough to be able to enjoy myself, to circulate with a drink in my hand and not feel as if I have to fuss with my clothes or accessories. And the indoor part has to work with boots and a winter coat. And I don’t want to have to shop.

All of my gatherings will be at restaurants or pubs. That is such a relief for me. When one is arriving at someone’s house in winter, boots must come off and be swapped for indoor shoes. And I always struggle to find something in my winter closet that looks good with indoor shoes. In winter I really, really prefer to wear boots: ankle boots, knee-high boots, whatever. Most of my outfits look best with boots. Including my faux leather pants which I will be wearing a lot this season.

So the other day I made a start with my planning and had an outfit-try-on session. I started with boots. And pants that look best with boots.

Like outfit #1, below. Which I’ll show you from the ground up. Or the inside out.

Outfit base: black boots, black trousers. Plus black cashmere sweater.

I started with one of the hero pieces of my winter closet, my faux-leather trousers. I rarely wear these in the fall, because they look ho-hum with sneakers or loafers. And they look great with my chunky Stuart Weitzman ankle-boots. The weight of the pants, the slightly wider leg, and the length, cry out for boots, in my opinion. Much as I love these pants, the style of the waist area does emphasize my middle. So, I prefer to wear them with a sweater that hits me about midway down my problematic midriff. Like this light-weight cashmere crew from Everlane.

Avec le scarf

I added black hoop earrings, an old grey and black animal-print scarf, and my beloved Max Mara green coat. You can find the coat here in blue. Mine is size 44.

I love this outfit. It will be perfect for the pub evening with the hockey gang we’ll be attending soon. Dinner, drinks, old friends, laughter, live music… I’m so looking forward to that evening

And finally, add a great coat.

Outfit #2 is what I plan to wear to a festive lunch with a bunch of girlfriends at a local restaurant.

Festive lunch with girl friends.

The base is the same as outfit #1. Black Stuart Weitzman ankle-boots and black faux-leather trousers. I added my Uniqlo ultra-fine merino crew-neck sweater which I took to Portugal and sadly wore only twice. This sweater is a great piece. Mine is the wine colour in size large. I’m even thinking of buying another one in the cream.

I like the sweater with the black tailored vest I bought last summer and a pair of dangly earrings from Anne-Marie Chagnon. The tailored vest turns the sweater and trousers into an outfit. And finally a multi-coloured gauzy scarf pulls together the wine sweater and the raspberry tweed Max Mara coat with the black pants and boots. I can’t tell you how many years I’ve had this scarf. But every year I find I’m glad I bought it. Sometimes I think that scarves are what really make winter outfits work.

As you can see, below, outfit #3 marked the end of my outfit-try-on patience. I’d pulled too many sweaters on and off over my hair. And I was anxious to get outside, take a few more photos, and go run my errands before I started looking like “Aggie Witch,” as my mum used to say when, as kids, we looked particularly wild-haired and disheveled.

I love this grey and white cable-knit sweater from Vince. And I especially love it under my off-white ultra-light down jacket from Uniqlo. What a good buy this coat was. I’ve worn it a ton in the past five years. With skirts and pants for good, with jeans and ankle boots for errand-running, and even with my rubber boots and rainproof pants for walking. I’m thinking I may have to buy another one before I wear this one out and then discover that Uniqlo has stopped making them.

I love this jacket with the grey sweater and black pants

Outfit #3 is a simple, casual, comfortable outfit to wear out for drinks with the girls. Or shopping and for coffee with a friend. One thing about wearing this sweater with slippery faux-leather is that the bottom ribbing doesn’t stay folded under in the front like I prefer to wear it. So I used two safety pins to keep the front folded, and let the back hang down a bit. Perfect.

Okay, that’s me sorted for two “event” outfits. Plus one miscellaneous outfit that I will pull on when I need it.

Now, back to winter, and winter dressing, in general.

I love winter… and I will until about late February. Then I will long for spring. Right now, I’m excited to haul my winter coats, sweaters, pants, skirts, scarves, and hats out of the closet and find new ways to wear them. And old ways that slipped my memory until Pinterest or an old blog post reminded me.

It’s just the boot thing that gets me about winter sometimes. All my winter outfits are designed around a pair of boots. I plan the outfits from the ground up, so to speak. With boots as part of the outfit. Which is great for shopping or going for drinks, eating out in restaurants, or otherwise visiting public places like museums. And not so great when one is visiting indoor spaces where wearing boots would be rude, or unacceptable.

I mean, winter dressing is complicated enough. One has to be happy with the outdoor part of one’s outfit: coat, boots, scarf, whatever. And one should be happy with the indoor part of the outfit, how it works with the outdoor part, but also how it works once the coat has come off. The indoor part of the outfit must be warm enough, it is winter after all, but not too warm. Sometimes if a room inside is cold, it is wise to plan to be able to use part of the outdoor outfit, like a nice scarf, to keep warm. Like I said, it’s complicated. So to have to plan what boots one wears, and then what shoes one will change into greatly complicates an already complicated formula.

And don’t get me started on having to unexpectedly take one’s boots off, when one doesn’t have a pair of shoes in one’s bag. And when, say, hypothetically speaking, one is wearing knee-high boots with a skirt which will then look ridiculous with stocking feet. Now, that can totally ruin one’s outfit vibe, people.

Unless one has a really great pair of socks.

Almost one with my environment.

Maybe I should up my sock game. That’s what we did when attending winter house parties in university. We made sure we had on great socks.

Maybe that should be my modus operandi when I know I will have to take my boots off and the shoes I own don’t make the cut.

Or for those emergency situations when I don’t know ahead of time that I’ll be required to remove my boots. Maybe I should stash an emergency pair of warm and wildly colourful socks into my bag. Just in case.

It might work, you know. Instead of awkwardly tiptoeing around in my tights, I could wear wildly patterned colourful cosy socks that look intentional. And chill. And as if I didn’t mind being bootless in the least.

Don’t you love my pom pom?

Of course you know, if you’ve been reading my blog for a while, that some of what I’ve written here is in jest. And some is hyperbole. And some is not. I do struggle to plan winter outfits for indoor events. What to wear with what can keep me awake for nights. Shoes are the bane of my winter party outfit-planning existence. Not to mention winter festive party outfit-planning.

I mean, I could just go out and purchase festive party-specific outfits complete with appropriate footwear. But I don’t want to do that. Just the thought of tramping around malls, lugging my coat and my bag, trying on spangly tops and pants or silky dresses that I might wear once a year gives me the shivers. I don’t do fancy dressing. And I’d never find anything that suited me.

I’d rather stay at home and read my book. And then do just what I have done. Dig around in my closet for something that does suit me.

To be honest, I do have a few things that might work for a house party, even a winter festive one. A vintage velvet bolero, a silk blouse, an old pair of skinny black pants, a pair of pointy-toed, low-heeled pumps (like these except mine have a bow).

But like I said, this year I don’t have to worry about all that. I can wear my boots.

P.S. I quoted my mum again in this post. How she used to say that we looked like “Aggie Witch” if we had wild, unkempt, disheveled hair. I have no idea where that expression came from, or to whom it referred. I always assumed Aggie Witch must have been a comic strip or television character. But I never asked. Now I wish I had. Maybe it’s not a pop culture reference at all. Maybe it’s just a family expression like wearing one’s hat with a “McCarty slant.”

P.P.S. The clothing links in this post are affiliate links. If you make a purchase after clicking my link I will earn a commission which helps to pay for the blog. Here’s the link to my faux-leather pants from Aritzia, mine are size 12, if you’re interested. This is not an affiliate link.

P.P.P.S. If you are interested in any of my Uniqlo pieces… I just wanted to say that I am unable to provide a link to the exact item on the Uniqlo site. My link automatically converts to the general site. I don’t know why. So I’ve try to describe the pieces I wear in the exact language used by Uniqlo so you can more easily navigate the site. Hope this helps


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49 thoughts on “Winter Dressing From the Ground Up”

  1. I vote for channelling your uni days by wearing (or bringing) colourful, cosy and wildly patterned socks! I think it would look intentional AND you would feel comfortable!
    I felt your pang with your reference to Aggie Witch and questions never asked…
    Enjoy all your outings! You look fantastic!

  2. It’s interesting how things are done differently in different areas of the country. Out here in Alberta, everyone takes their shoes or boots off at the door, both at home and when visiting someone else. Socks or slippers are worn indoors.

    1. Same here, Elaine. If I’m dropping by someone’s house for a visit or a cup of tea, shoes or boots come off automatically. But most of the special occasion house parties or dinner parties I’ve attended these last few years, the female host and most of the female guests are all wearing indoor shoes.Everyone changes their outdoor footwear for indoor footwear at the door.

  3. Seems like you’re all set for the festivities & looking great . I saw your green coat in the blue last time I was in town but green is better . I enjoyed my whiz round the shops but it annoys me having to wade through all the sparkly Christmas stuff . I don’t know whether that’s because it’s just not my style or because I wish I had the party lifestyle that everyone else looks to have ! I always wonder where the unsold sparkles go come January the first . Like you , I love pulling out my winter stuff & it’s funny how your eye changes . I have a coat that seemed a little too big & loose with sleeves a little too long so it didn’t get worn much . It’s perfect now & my neat fit coat isn’t my favourite any more .
    I like Carmen’s latest handiwork .

    1. I’m the same, Wendy. I am loving my looser fit green Max Mara coat so much more than my neat and trim tweed coat. I did a quick walk through of the sparkly stuff in a couple of stores last week… everything looked so cheap. I’ll stick with the stuff I already own.

  4. Love all of your outfits, especially the burgundy jumper and coat. Very chic and warm looking. Also agree with the snazzy sock idea.
    I know what you mean about winter dressing. Many years ago I passed out in a department store in London as I had too many clothes on. Unfortunately I had forgotten about the heating!
    We are at the opposite extreme at the moment – how to dress up a bit for the seasonal festivities but managing to stay cool while allowing for aircon which can, at times, make you wish for a down jacket. Humidity doesn’t help either – especially on the hair front.

    1. Yes, I can see that you guys are dealing with the exact opposite problem… dressing for the outdoor heat and the artificial indoor cool. And then the humidity… 🙁 … at least when it’s very cold it’s usually not humid.

  5. Rain is the problem here in the UK. Rain and wind. We have had a lot of both recently, with flooding hard on the heels. Boots for me, always, the stouter, the better. Warm trousers. Jumpers. Scarves, gloves. But not hats. I have never been a hat person. Off out to lunch today with friends and it will be shirt and jeans, with scarf to keep draughts at bay. Boots and velvet gloves.

  6. Hi Sue,
    All of your choices look great … classic and stylish, very you!
    I share your dislike of Mall or Department Store shopping, whilst wearing heavy layers for the chill outside. Not a pleasant experience!
    When I do go I’ve recently noticed a lot of women with “carry on” size cases and they surely they can’t all by travelling 🤔. I thought maybe they put their shopping in them but now I’m wondering maybe they use it for their outdoor coat , scarf etc … and I’m thinking what a great idea! 😂

    Even before I noticed that Kristin had asked about your grey knitted dresses, I’ve wondered for a while now why you haven’t mentioned them. I think they’d be perfect for some of your evenings out and for house parties. I wear mine for similar occasions.
    Fancy socks ( or pretty tights ) are the best, just in case you need to remove your boots!

    There’s so much that I often wish that I’d asked my mum … and like you and yours, we talked regularly about all sorts!

    I hope that you’re starting to feel much better and able to enjoy all your pre Christmas festivities!

    Rosie xx

    1. I wonder how those bags work in a crowded store… is everyone tripping over everyone else’s bag? Ha. I am feeling better, thanks. Went to a long lunch with a group of girlfriends and didn’t even start to cough until the end. Then came home and had a long nap. Post-Covid management. Ha,

  7. You look very pretty and classic in your outfits.

    I tend to step a little bit out of my classic looks into festive season looks, but nothing outrageous! I like to add a little bit of sparkle or velvet that I keep in my closet for just such occasions.

    I agree with you about heavy coats and the mall. Some parkas have the inside straps so that one can wear them like a backpack. I do that sometimes…but generally I simply avoid the mall at this time of year. When I’m shopping in Europe it’s all outside and in little shops, so the coat issue doesn’t arise.

    I do most things on foot so I’ve accepted the fact that I have to wear heavy boots and coats over nice clothes. I don’t worry so much about that incongruence. I recently bought a really long parka and I’m thrilled to finally have coverage so that I don’t end up with salt splashes on my tights or pant legs. Small victories!

    Hope you are feeling more energetic and enjoy your upcoming Christmas events.

    1. So true … walking to work in winter is a whole other thing isn’t it? I remember vividly living in the Glebe my first year teaching. Outdoor dressing was all about not freezing to death on the way to my numerous bus stops each day.
      P.S. I still haven’t made my pre-Christmas trip to Bank Street yet for a browse around the shops and to just soak up some neighbourhood shopping.

  8. Chère Sue , En Provence nous n’avons pas de neige en hiver et elle fond actuellement en montagne !
    Il est prévu 20 degrés centigrades la semaine prochaine !!!!
    Moi qui aime tant le froid ,le givre qui crisse sous les pieds ,l’air frais qui vous revigore !!
    Au final je possède des vêtements d’hiver que je porte rarement . Nous en sommes encore au chemisier sous un blazer léger en laine !J’en possède de toutes les formes et toutes les couleurs !
    Et je porte encore des escarpins avec des bas fins !
    Nous vivrons peut être un vrai hiver quelques jours en janvier -fevrier , avec de gros pulls et des bottes .On peut rêver …

    1. I particularly love the crisp air this year because nothing clears my still stuffy head like cold fresh air. Wearing my favourite coats is, of course, an added bonus. 🙂

  9. This topic reminds me of winter party-going where some chic guests would bring their pumps in a shoe bag and then change at the door. Are shoe bags around nowadays, and if so do tell us where!

    1. I just recently donated a leather shoe bag I had had for years. I find that even at the faciest parties we are required to leave footwear at the door. I think people are afraid of getting their hardwood floors damaged by heels or dirtied.
      I see a few have mentioned your sweater dresses for your Christmas events. They would be dressier than leather pants and still comfortable. Add some lovely earrings, maybe a bangle, or two, and you would look and feel party ready. You could, also buy a sweater with a bit of silver in it to up the festive feeling. Your outfits, while stylish, are a bit casual for a Christmas party.

      1. I have had the opposite experience, Joanna. Guests and hosts at house parties I attend are almost always wearing indoor shoes. Not high heels, of course. But nice flats which don’t damage floors. P.S. The grey midi-dress is always in rotation. 🙂

  10. I absolutely love the first photo head shot of you! Striking and pretty.

    I used to pin my clothes to do what I wanted them to but noticed I was ruining some of them/the material. I found clothing magnets work great and don’t pull or snag, etc. Scarves stay in place, hemlines tucked up, ruffles or pussy bows lay flat and right. They also saved me a few times when I ripped out a pant hem, holding it up till I could repair at home.

    Thought I’d share the tip should it help anyone else!

      1. Shepherd’s Fashions store sells Maggie Magnets – various colour of rings & magnets in one package. The magnets work great for holding scarfs or ponchos in place, as the magnets are quite strong.
        Enjoy all your outings, Sue. All of your outfits look great!

  11. I enjoy reading all the comments and your replies. I have nothing to add but would like to know what size you wear in Uniqlo light down jacket. Just gave away my one in medium. Not sure if I should order large or extra large! I’m 5’5” and 130 lbs. I appreciate your input.

      1. I’m right in the middle of you two, 5’6” and 135 lbs. I brought a medium and it’s perfect! 😉

  12. Living in Australia, even in the South which does get cold, your autumn dressing is pretty much as far as we go. a thin jumper with a coat over or thicker jumper and jacket covers every eventuality. we never get snow but we do get a fair amount of rain. my aquatalia ankle boots are my best friends

    1. Do the mountains in Victoria still get snow, Noreen? Or has global warming out the kabosh on that? I remember so clearly when we drove the “Great Alpine Road” to Bright in 2003, and the signs that said in which months chains on the car tires were recommended. Guess you are bracing yourself for the heat these days.

      1. there is still snow on the mountains in NSW and Vic Sue but not a lot, and not for very long. our ski season is about three weeks! Victoria is getting hot and humid weather, more like queensland than the dry heat we used to get.

        1. We stayed in the Snowy Mountains, Mount Kosciuszko, when we were there in 2008. Not during ski season, though. 🙂 I am sure you are not loving the increasing humidity. Heat and humidity are such a double whammy.

  13. I’m a native Southern Californian, 2nd generation. While I love all your outfits, I don’t have the same opportunities to wear your beautiful layers. I’m not boasting here. My younger sister moved to the East Coast decades ago for Love AND the opportunity to wear more winter fashion! At the time, she was a visual designer for Banana Republic in the Washington, D.C. area. She’s still there…with the same Love. 🤗
    I do have a collection of much-loved fall and winter sweaters.
    Today, I did wear my beautiful wool cardigan my mother bought for me in the British Isles decades ago. I love that thing and strive to keep it in good condition. Amy hints you can share on the care of your beautiful sweaters, coats, etc. would be greatly appreciated.
    You look great in all your outfits and continue to inspire me. Glad that you are on the mend and planning to get out and about!

    1. Thanks, Charlene. I don’t have any special tips for sweaters. I just wash them by hand a and lay flat to dry. And de-bobble them regularly.
      P.S. Love that story about your sister. 🙂

  14. Just got back home from a week of Christmas Markets in the Mosel and Alsace, and got to remember once again the joys of winter wear! Took my loyal puffy coast that I bought in Boston in 1995 (it didn’t get a lot of wear in Southern California) and the Sorel boots I bought last year. And layers. Lots of layers. I’m thinking that silk long underwear might be on the shopping list before next year’s markets.

    1. I bought silk long underwear (very light, long-sleeved top and bottom separates) over 20 years ago when I regularly visited Ottawa because my husband was living there. They have repaid their purchase price (which was modest, they were a house-brand staple of Eaton’s a now-defunct Canadian department store) many times over with warmth. Highly recommended!

  15. Well to any of the nay sayers re your black pants I say if you don’t live in Eastern Ontario, step off. You know that slush that sticks or splashes onto the back of boots or tights or pants? Easily wiped off your faux trousers! Very practical for our clime Ms. Burpee! It doesn’t hurt that they look smashing on you too! That photo of the three women in the cold looks great until I saw the wide pants dragging in the slush.. if I was a hostess and they entered my house..I’d be offering them dressing gowns to wear, do not drag that stuff into my house!
    No I spent years wearing wide flare pants in my younger years dragging through Toronto slush, Ottawa slush mixed with salt…is much, much worse in the urban core. No wide pants dragging for me..leggings in high boots with a cashmere tunic or thick, blackout tights with a warm dress and high boots. Women I worked with who walked to work wore snow pants and practical boots with flip down metal cleats for icy days..I import my cold weather fashion style from the true fashion queens of the North, Les Montréalaises…once I noticed that no chic woman goes out in minus weather without a toque with a fur pompom I created a little wardrobe of them with matching fleece lined mitts! Mine have recycled real fur Pom poms that snap off when washing the hat. They are lined in fleece, so warm, so stylish, so Québec!
    Honestly I saw a young woman walking home from high school the other day during a snow storm with open coat BARE midriff and well exposed bosom..made my old bones shiver just to watch! ps I just bought a pack of snazzy Nordic knit socks, very colourful, they are intended for gifts but I’m keeping a pair to wear inside at winter parties..we’re a casual gang so most people just wear socks inside or bring their slippers, my one homage to holiday bling are a pair of silver sequin flat indoor mules which look good with any pant or skirt.
    Rain this week..a whole new challenge!

    1. Yes, those faux-leather pants are really easy to clean up. Much like the slippery snow pants we wore as kids. Ha. And I agree… no one does deep winter fashion like Quebeckers. I still remember a winter visit to old Quebec City back in the eighties. I was very impressed. Not just with the fashion but with the determination of locals to wade any amount of snow to go out for drinks and dinner.

  16. Oh yes! I have very UN-fond memories of shopping in the Rideau Centre after having walked about twenty minutes to get there. Walking on ice and snow in -10C temps (lower than that and I don’t go out! ;-)) means all the layers you’re talking about and entering the mall I’d have about five minutes before I started peeling them off and having to shop while carrying a hefty coat. You have ALL my sympathy.

  17. The coldest the day time temps where I live during last winter was about 10C ( 50F ) and then it dropped to a low of -4C ( 23F ) at night, so rugging up wasn’t as necessary as the northern part of the world.

    During the day I was comfortable enough in a thermal top under a chunky knit poloneck and jeans or a cashmere poloneck layered under another sweater with a winter jacket or coat as necessary at night.

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