It seems that I have spent much of my life in menswear. Not literally. Although I did work in the menswear department at Simpson’s Department Store here in Ottawa for a few months in 1979, before I was transferred to cosmetics. So for a while I was literally “in menswear.”
And when I think about it, I have been known occasionally to wear men’s (or boy’s) clothing. Literally.
Like the year I stole Hubby’s treasured suede vest that he bought for twenty-five cents at a market stall in Amsterdam in the sixties. And for a while in the nineties I wore it with a tee shirt, jeans, and ankle boots. Or when I raided my step-father’s handkerchief drawer in the seventies and stole a red and white polka-dotted handkerchief to tie around my neck because they were all the rage at school.
Or in grade ten when my friend Debbie and I shopped in the boy’s department at K-Mart to find tiny, striped polos that gave us the perfect shrunken style we craved. Sadly my shirt didn’t last long because my Mum gave it away to a young male cousin who was visiting. She found it in the wash and thought it must be an old one of my step-brother’s that had shrunk. When I protested, she was unrepentant. Why did I need a boy’s tee shirt, anyway?
More recently I have had to resort to buying men’s athletic pants, like the heavy Gortex ones I wear fishing, because the women’s pants are always too short and too big in the hips. A couple of years ago I bought a pair of men’s 511 Levi’s because I could not find women’s jeans that suited. So yeah, I have been known to wear actual men’s clothing. Especially when I cannot find what I want in the women’s section.
But what I mean when I say that I seem to have spent my life in menswear is that I have spent my life longing to be in menswear. I’m referring to my long-held preference for men’s styling. For the simple, clean lines, and sharp tailoring of men’s jackets. Loose, but not flowy, dress pants. Flat leather boots with jeans. And for shirts with stiff collars instead of soft blouses. What I want more then anything is menswear-inspired women’s clothing. And to be able to carry off a menswear-inspired look with the insouciance of Emma Thompson in her suit and sneakers at Buckingham Palace in 2018. Or Lauren Hutton in that famous white suit in 2012. Or Charlotte Rampling walking the runway for Alexandre Mattiussi last January during Paris Fashion Week.
You know, the older I get the more I think that older women look amazing in menswear. Or at least in menswear-inspired looks. That shot of Charlotte Rampling on the Paris runway in her suit inspired me to go down this rabbit hole a couple of weeks ago. And in that serendipitous way that life and fashion and research sometimes have, I stumbled upon tons of examples of what I’m talking about.
In a recent newsletter Leandra Medine Cohen wrote about ramping up her winter outfits after seeing the menswear-inspired looks Victoria Beckham was showing for pre-fall 2024. Sharply tailored, loose-fitting suits, with layering under the jackets. Creative uses of turtlenecks or scarves, crisp shirts, and hoodies. A look that Leandra calls “shirt sandwiches.” That description made me laugh. She does have way with words does Ms. Medine-Cohen. You can read Leandra’s full article “The Styling Tip That Launched a Million Outfits” here, if you’re interested. And you can see the whole Pre-fall 2024 offering by Victoria Beckham here, if you like.
Once I had read about the “shirt sandwich,” I began to see it everywhere. I also found lots of menswear-inspired crisp shirts under sweaters with blazers. Or shirts under sweater vests like the Me&Em outfit above. Or turtlenecks under shirts left open over jeans or tailored dress pants with over-size blazers. I love the charcoal grey and soft blue example I found on Pinterest above. And when I had exhausted the search for inspiration, I set aside an afternoon and gamely tried the whole layering with sweaters, shirts, and jackets, not to mention the “shirt sandwich” idea.
I have to confess, that was not a successful try-on session, my friends. Not even close.
The shirt sandwich thing is a no-go. It made me remember why I stopped wearing shirts under sweaters under blazers years ago. So uncomfortable. So darned uncomfortable. And don’t even get me started on the pain in the butt it is to pull on a shirt over a turtleneck before one even thinks of donning the blasted sweater. The twitching of collars, and twisting of sleeves, the tucking, then the inability to raise one’s arms if the tuck is too tight. I’m frustrated just writing about it.
I tried the turtleneck under a shirt left open under a blazer, like in the inspiration photo above, and it just looked silly on me. Too contrived.
Finally I condescended to try my old blue Equipment shirt under my light-weight Everlane cashmere crew partially tucked into my Aritzia black dress pants, and worn with a belt and my knee-high black boots. This I could do. This one was… okay. I didn’t love it, but it was menswear-inspired. And it wasn’t uncomfortable. But, you know, I can’t see myself hauling this on to go shopping or out for lunch or coffee. It’s too much like business wear for my retired lifestyle.
I gravitated much more to the idea of a chunky turtleneck (see inspiration photo above) with my dress pants, than the shirt and sweater combination. This loose cashmere turtleneck I bought from Aritzia just before Christmas gave me the exact look, and feel, I wanted with the dress pants. Looseness, ease, comfort. And with the boots, a slightly mannish look. As a concession to the layering idea I was supposed to be attempting, I tucked an old scarf into the neck of the sweater. I like this look.
The black and red and olive green of the scarf pulled the black sweater and pants and the green coat together perfectly. Thanks, Mum. Mum bought me this scarf for Christmas back in the eighties. She said she was Christmas shopping for something else, saw this inexpensive scarf, thought the colours would be good for me, and bought it to add to the rest of Hubby’s and my Christmas care package. Never ever give away scarves, my friends. They always fit. And to be able to paw through your scarf basket, years later, and pull out the exact colour you need for an outfit is so satisfying.
I wasn’t ready to be done with this topic, though. So yesterday I did a second try-on session. With jeans and jackets. I love the look of faded jeans and a sharp menswear-inspired blazer with boots or sneakers. With sweaters around shoulders, maybe, instead of crammed under the jacket. Here are some more ideas that I found on Pinterest. You can see my Menswear Inspired Pinterest board here if you’re interested.
I bought these split-hem Zara jeans, below, last year in my quest to find jeans that have a slightly relaxed fit and are long enough to wear with boots in the winter. My men’s 511 jeans are slightly too short for boots; I prefer them with sneakers. And the Levi’s 501 “dad jeans” that I bought in 2022 are way too short for, well, anything really. I’ve tried those jeans on and then taken them off again more times than I can count. I don’t know what I was thinking when I bought them. I plan to consign them this winter when I am on my tour of Ottawa consignment shops.
The best thing about the outfit, below, is the baby blue long-sleeved tee and faded blue jeans with the deep green. I love that combination. And I love how this Prada sweater goes so perfectly with this old Max Mara tweed jacket. The jacket should be more oversized to be able to replicate a totally current look. But I love this old jacket. And I decided last year to forgo searching for an oversized blazer. I think that trend has run its course. And if it hasn’t, I still can’t justify jumping on board when I have lots of blazers in my closet.
The only problem with this outfit is that it’s more appropriate for fall. The sweater over the jacket won’t work when I add a coat into the mix. I might swap the sweater for a scarf and wear my long, winter green dress coat, though. That might work.
Now this outfit, below, is one I would totally wear. And will. It’s just menswear-ish enough for me with the sharp blazer, the loose jeans, and rather western-looking boots. I started out with the Vince light-weight turtleneck tucked into my jeans, a black belt, and this old Max Mara Weekend jacket. But I thought it needed a third colour. This scarf bought at Simons in Montreal on our girls’ shopping break in 2022 is perfect. You can read about our trip here. The shade works with the colour of the jeans without being so similar that it looks matchy-matchy.
And then I thought a cheeky men’s tweed flat cap would add the je ne sais quoi I wanted to this outfit. Hubby and I bought this cap for my step-father in Edinburgh in 2005. Like Hubby, my step-father had Scottish ancestors. As one man said at our B&B, “You Canadians, you’re all Scottish.” I begged to differ, though. Saying that there were a fair few of us who were Irish, too. And French, and English, and African, and Italian, and Ukrainian, and Polish, and Japanese, and Indian, and German, and Somalian, and Vietnamese. No to mention all the original peoples who were already here when we Europeans arrived. He got the picture. Ha.
But I digress. We brought the cap home to New Brunswick. Lloyd loved it but only wore it once or twice because it was “too good.” And when he passed away, I brought it home with me. So voila. I love it. So I’d better start wearing it, hadn’t I?
So that’s the story of my life in menswear lately. I’ve been thinking about this post for a while. I do love a beautifully cut, menswear-inspired coat or blazer or suit. And flat boots with jeans. And even crewneck sweaters with shirts under them. Although clearly not as much as I liked them in university. Back then a shirt, with a scarf tied like an ascot, sometimes under a sweater, or with a blazer, and jeans was an outfit I wore often. As you can see below. My high school buddy Jeannie sent me this photo a while ago. I’d forgotten how dark my hair went in my late teens and early twenties.
I loved the charcoal velvet blazer I’m wearing in the photo. And the chambray denim shirt with the western-style snaps. It was my friend Jeannie who taught me how to tie a square scarf around my neck like an ascot. She was always so good with clothes. Way better than me. We haven’t seen each other for a few years now, but we still message regularly to chat about books, and tell old stories, and to consult on possible new wardrobe acquisitions. Ha.
While I’ve been putting this post together I’ve been rethinking the three adjectives that I chose to define my personal style. If you remember I talked a lot about that idea a while ago. Especially in this post. And I arrived at “classic, modern, and minimal” as my three words. With “chill” or “edgy” as my aspirational fourth adjective.
Retirement and letting my natural hair colour grow out made me rethink how I dressed. And how I wanted to dress. I kept thinking that my style needed to be more edgy now that my hair was white. Less fussy, neat, and polished. I finally stopped putting a crease in my jeans. That’s progress, isn’t it? And this journey down memory lane, about how I have always loved menswear-inspired looks, has given me pause. And made me think that I need to rethink things.
Oh, I do love a re-do, my friends. I’m not there yet. But I’ll get back to you when I am.
So how about you? Are you a fan of the menswear-inspired trend? If in fact it can be called a trend. It’s been around for ages. I mean, think of Katherine Hepburn or Marlene Dietrich. Is there a look that you have gravitated towards in one way or another for most of your life? Do tell. We’re dying to know.