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.
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.
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.
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.
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
Outfit #2 is what I plan to wear to a festive lunch with a bunch of girlfriends at a local restaurant.
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.
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.
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.
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 since Aritzia doesn’t support bloggers.
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