A Fulsome Discussion About Winter Boots

I knew it was coming one day. I’d have to capitulate and buy winter boots. For the first time in decades. And so I did, back in early November. They’ve been sitting in their box, “seasoning”, as my mum says, until I was ready to wear them. And the time has come, my friends. For warm boots. And for a discussion about boots. Whether I’m ready or not.

But before we get into that discussion let me introduce you to my new winter boots. They’re from Ugg. A brand I never thought I’d ever wear, given the ubiquitous, suede, squashy Ugg boots on the feet of every teenage girl, or so it seemed, back when I was still teaching. I used to look at their boots and, I kid you not, I’d think, “Ugh. Not Ugg.” But time changes, as do brands. I still hate the original Ugg boots. They look too much like cartoon feet for me. But these, these boots are just what I need. And I love them.

These are my new Ugg Adirondack winter boots.
I love my new winter boots from Ugg.

I should back up a bit and explain my earlier remark about not buying winter boots for decades. One would expect that, living in Canada, I must own winter boots. Especially since it’s so cold and snowy here. And especially since I love boots so much.

My relationship with boots has not always been a convivial one. I wrote a post about boots and my thoughts about boots a while ago. You can read it here if you’re interested. In this post I wax nostalgic over boots. The dreaded galoshes we wore as kids with the sad little fringe of fur at the top. How we wore plastic bread bags in our boots when they leaked. And the move into fashion winter boots when I was a bit older. Fashionable winter boots that looked smashing on other girls with their sturdy legs and their mini-skirts. But not on me.

As a tall gangling adolescent, with sticks for legs, I sighed and moaned about the fact that other girls could find knee-high boots that fit their legs snugly, and looked cool with mini-skirts. Me, I didn’t even have to unzip mine to take them on and off. My long skinny foot and leg just slid right in and out. Sometimes even when I was trying to keep them on. Ha. I’ll never forget writing in my journal in grade nine, that, after weeks of training for the basketball team, my legs were “getting fatter!” I could tell because they filled out more of my winter boot. Gad. I’m not sure how my mother endured all the drama.

I bought my own boots for the first time the year I was in grade ten. With money earned by working for my aunt Phyl at the canteen in the Beaverbrook Rink. They were the first pair of boots that I loved. Tall, lace-up, brown leather granny boots, that I could cinch tightly to fit my legs. They were cool, so cool. But they were not winter boots. I froze my proverbial off waiting for the school bus all winter, but I didn’t care. I chose fashion over warmth.

Since that time, I’ve always bought boots to look good and to go with my outfits, snow and slush be damned. I still remember the burgundy leather, knee-high boots I ruined the winter I worked in pharmaceutical sales and had to wade snow and salty slush in parking lots every day in my beautiful boots. But they looked cracking with my long taupe winter coat. Since ankle boots came into style in the nineties, I’ve usually owned black and brown tall boots, and black and brown ankle boots. Always leather or suede boots, never proper winter boots.

Hubby once said he thought the number of pairs of boots I owned was excessive. Why did anyone need more than one pair of boots? D’uh. I couldn’t be expected to wear black ankle boots with a brown pantsuit. Sheesh. What seemed excessive to me was investing in a pair of winter boots that would look terrible with my outfit and which I’d take off as soon as I arrived at work.

Maybe I should explain that I usually wore my boots all day because they were always part of whatever outfit I was wearing. I love the look of a knee-high leather boot with a midi-skirt. Or how a brown ankle-boot looks so lovely disappearing up into the leg of a brown dress pant. And the warm winter boots I saw in stores just could not compete. Besides, I didn’t really need them. For those days when I wasn’t wearing my good clothes, I owned rubber fishing boots, sturdy hiking boots, and warm ski boots, and they were sufficient to my needs.

Wearing my Ugg Adirondack winter boots with an Adrienne Vittadini blazer, Massimo Dutti jeans, and a Gap sweater.
Wrapping up to go out in the snow.

Now besides my fishing, skiing, and hiking boots, I own several pairs of leather ankle boots that I wear all winter with my jeans. From house to car, and car to shopping mall or restaurant. And a tall pair of suede and leather boots, bought years ago, which I wear on the occasional day when I need to tuck in my jeans and wade snow. But they’re not really warm. They’re a house to car, and car to restaurant kind of boot too.

Not since I was a kid have I needed a dedicated warm winter boot for romping in the snow. Until now, that is.

Since I retired and no longer spend most of my winter days inside a school. And my winter wardrobe is trés casual, and not professional-wear. Since my old sturdy hiking boots bit the dust, and I discovered that my new light hiking boots, which are wonderfully supportive and great for travel, are not so great for walking in the winter. Now that Hubby and I are walking later and later in the season when there’s some snow, but not enough to ski. And since I’m even more determined to be outside for my exercise as much as possible… I’ve decided that I need a pair of warm, comfortable boots to walk in the snow. And maybe even romp if the spirit moves me.

If those boots also look great with my Massimo Dutti khaki skinny jeans, an old cream wool sweater from Gap, and my ancient Adrienne Vittadini camel jacket. And the lovely new cream and grey scarf I bought when I was supposed to be shopping for Christmas gifts. Well, all the better. I’m kind of excited to pair my new boots with my black jeans and my cream down jacket. Or with my dressy Max Mara alpaca coat and jeans. I’m even excited for winter weather.

You know, I would never have picked these boots off the shelf if the young sales assistant at Brown’s Shoes hadn’t suggested them. I’m so glad she did. They are just the ticket. Kind of funky looking. Kind of old-fashioned looking. Not too girly, or old lady-like. Not galoshes by any means. Ha. They’re waterproof leather, suede from just above the ankle to the tops, and the tops can be worn turned down with the fur showing or not. They have soft, warm, furry lining, with a furry innersole. Soft enough to go barefoot in them, so says the salesgirl. Ha. Mine are caramel and black, but they also come in several colours. As well as a taller version. I’ve linked them below.

So I will be all set for winter walking. And for braving the elements to run errands on those days when I might possibly ruin my good Stuart Weitzman black ankle boots or my suede over-the-knee boots in the slush and salt of a Canadian winter.

My first pair of winter boots in years are these Ugg Adirondack boots.
These boots are made for romping.

Here’s a selection of Ugg Adirondack boots. I also liked the grey ones. But I demurred on the pure white boots, with white fur. I laughed out loud when the salesgirl showed me those. They looked a little too much like the white furry boots I wore when I was a toddler. The ones that matched my white faux-fur snowsuit. I know I’m regressing in many ways, my friends, but wearing those would be a step too far. Ha.

So that’s all I have to say about boots today, folks. I hope you’re ready for winter or for whatever kind of season is coming your way: snow, rain, or even extreme heat if you live downunder. What is your footwear of choice for the next couple of months? Besides slippers that is. Ha.

P.S. I sure hope that you are still planning to join us for our imaginary Paris getaway. I’ve received a couple of photos already. Thanks Dottoressa and Wendy in York. Maybe some of you took a photo of your Thanksgiving Day outfit, if you celebrated Thanksgiving? Don’t forget that you don’t have to send your dressy dinner outfit. Comfy travel clothes, sitting and yakking with the other ladies outfits, shopping outfits… whatever you can manage. We just want to see your smiling face on the post. I will be writing our Paris post this week for publication on Saturday. So if I have the photos by Thursday, Dec. 3, that would be wonderful. You can send them to me here.

P.P.S. The links to boots in this post are affiliate links. If you make a purchase after clicking my link, I will earn a commission.

Joining Catherine over at Not Dressed as Lamb for her #IWillWearWhatILike link-up.


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30 thoughts on “A Fulsome Discussion About Winter Boots”

  1. Well, even though I live in So Cal I have two pairs of winter boots in addition to ankle boots in black, red, burgundy, pewter, taupe and brown, and knee high boots in black and brown plus over-the -knee boots in black and burgundy. I bought the first pair of winter boots for a Lake Tahoe trip several years to wear in the snow. They’re Ugg’s but don’t look like them. Then last year I saw a Cole Hahn pair on sale and I bought those for my trip to London. They were so comfortable , I walked miles in them. I like wearing ankle boots because the provide support for my ankles, one of which I suffered a traumatic injury. I walk more securely in boots. I must confess I haven’t worn the over -the-knee ones yet but they were very inexpensive. I like to travel in fall and winter and boots hit the spot.

  2. I like your boots! They look comfortable and warm and not clunky (unlike the style that gave Uggs a bad name).
    I remember the thrill of getting white “go-go” boots when I was in maybe 2nd or 3rd grade. Only later did I appreciate the sacrifices my parents must have made for such a purchase. In high school, I had “waffle stompers,” bought with my own money.
    When I lived in NYC, I (and all my female colleagues) had a desk drawer full of shoes, and I wore flats or unglamorous snow boots for the commute. There was no shame to it.
    I haven’t had snow boots since moving here. No snow! I do have moon boots for the times we’ve taken our kid skiing (the mountains are close enough to go for the day).
    That said, a day spent flâner in a French city can lead to cold toes, even without snow. Some furry sole inserts make a big difference in my tall black boots.

    1. I remember the winter I took three buses to my first teaching job. I had no car, and at the time could not afford to buy actual winter boots. So my old leather and not very warm boots had to suffice.

  3. I remember when knee boots were invented & I had the first ones in our small town – I was trendy Wendy then . These days I do lots of dog walking in all weathers & practical boots are very important to me . So many waterproof boots are not waterproof for long & I can’t abide wet feet . I wear ankle Muckboots everyday for an hour or two of walking & they’re great . Comfy too , though I always go down a size . But they are not trendy like your Ugg’s .

  4. After trying on many pairs of winter boots a couple years ago, I ended up with the same Uggs although I did get the tall version. They’re great! My DIL had them and highly recommended. Although I don’t wear them a lot (we haven’t had big snow often lately), when I want my feet warm and dry, they’re just the best. And I love the way you’ve styled them.

  5. I have collected several pairs of ankle boots in various colors. My Aquatalias are my favorites, impervious to snow and slush, though I’ve had great luck with Blondos also being waterproof. A couple years ago my husband suggested that I needed real boots, for Minnesota winters, and so I picked a pair of lace-up Keens that are just great. I’m sure that I will never need to buy another pair of boots! Yours look great for real winter

    1. I must admit that I think I need one more pair of boots. A knee-high pair of low-heeled black boots to wear with a skirt I just purchased. I may have to go shopping again. 🙂

  6. Welcome to the warm side Sue. Those boots look great for your outdoor adventures. I love the grey ones shown, and until now would not look at UGG boots due to the original look, but drool over those. After getting my first pair of Sorells a few years ago, I discovered the thrill of warm feet and realized that fashion boots are not meant for our winters. I did recently find a pair of Bogs at our Walking on a Cloud store and am really pleased. They are a dark cranberry waterproof 10 inch boot that is warm and soft inside with a -25F rating. The fun thing is that they have cut out handles for getting them on easily. This is the perfect solution to slush and wet snow. This week looks like I have to get out all the rest of the warm boots, a couple of which are short hiking boots that I wear with heavy socks rolled over the top. I just realized how many winter boots I have and may be a bit embarrassing to admit. Fun post Sue, and maybe the start of another collection.

  7. I love La Canadienne because they have boots for all seasons and they fit my narrow foot rather well. Pajar another Canadian company make great Winter boots. Those UGGs look like a copy of an LLBean style that has been around for years or Sorrel which used to be local and Canadian (could shop at their factory outlet years ago). There is lots of choice and don’t tell your husband but you might need to try some of the other companies….just to compare for the Blog lol

  8. I’ve always had the same opinion as you did about Ugg boots. Ugh! Have you seen their clear boots? Those are beyond Ugh! Quite hilarious, actually! Your new boots, on the other hand, look comfortable, cozy and perfect for our Canadian winter.

    I’m in the market for a new pair of tall black boots, but I have the same problem that you had growing up… skinny legs. It’s so hard to find tall boots that are narrow enough.

  9. I love your new boots. They look attractive and cozy warm. Growing up in Maine and, now living in Nebraska, I have and have had many pairs of boots (including a pair of original Ugg’s).

    I sure remember the black knee high boots I wore in high school. I walked a mile to school in my mini-skirt and mini-coat. Every day when I got to school my legs were purple/red and almost frozen hard!

    Years later when I was married and went snowmobiling, I hated the look of my boots, but they sure kept my feet warm. Nothing can ruin a fun day out in winter more than cold feet!

  10. PreCovid 19, I walked to work in the Financial District of Toronto almost every day, winter months included. I used to change my boots to a pair of office shoes once inside but for a 35 minutes walk morning and evening, I still wanted to look good 🙂 I could not bring myself to wear a pair of classic pants with snowboots, so I wore an urban take on combat boots from Massimo Dutti. It looked good but I was freezing. This is the first year when I gave in and bought a pair of Sorrels. Still have tags on them and would be tempted to return if not for a lockdown.
    Took me more than 20 years of living in Canada to buy a pair proper winter boots 🙂
    I like yours, I actually tried the grey ones. Pity that I don’t have anything grey in my wardrobe. Yet.

    1. I feel your pain, Irina. If I were still working I wouldn’t be wearing my snow boots to work. For walking and wearing with jeans etc I love them. Still… a 30 minute walk with freezing feet is not fun either.

  11. Hi Sue and everyone. With all the covid walking we are all doing, footwear really has to pull its weight. No slipping on the ice, big enough for a warm sock, comfy enough for the distance, and cute to boot! It’s been interesting this year to discover which pieces in my closet are the covid lifestyle stars. Sketchers slip-ons for house shoes and my brown leather lace up ECCO ankle boots for walking. Better than my hiking boots even. As our warm Calgary December turns into brutally frigid winter, the Sorels will be the boot of choice I think.
    As well, I have some UGGs that my mother bought in 2000. They are tall suede pull-ons BUT they have a wonderful muted folkloric cloth tape trim on then. Very Scandinavian looking. I’ve never been able to find another pair like them. I still wear them.
    Sweet memory of her they are.
    During a layover at the Amsterdam airport, coming home from Africa (!) I bought a pair of tall brown warm waterproof leather boots. They are my best friend on a really cold day. Not your typical winter boot shopping experience, but it turned out to be a good one. “Get ‘em when you see ‘em”. 😊

    1. Good footwear is so important isn’t it? I have been so grateful that sneakers are chic my last few trips. I’d still have been wearing them if they weren’t but so much nicer if they are.

  12. Seeing this makes me miss the snow from Upstate NY! But, even with a move to the rainy and comparatively warm PNW/US, I kept my Columbia boots. And my huge puffer coat. Maybe, somehow, it will snow ONCE this winter here? Or get cold enough to wear them? So far, even the snow trips to the mountains haven’t required them. Doubtful we’ll get snow in the valley… but I love them. The UGGS look great!

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