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 oversized turtleneck with the loose dress pants felt more me.

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.

Zara jeans, Max Mara jacket, Vince turtleneck, Simons scarf

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?

With Lloyd’s Scottish tweed flat cap.

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.

My menswear-inspired outfit back in the seventies.

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.

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55 thoughts on “My Life in Menswear”

  1. I love Diane Keaton’s distinct menswear style especially in the film Annie Hall. I was in my early twenties and remember watching that film and admiring every outfit she wore. She is a unique character and a true fashion icon. Although I have borrowed an occasional shirt or blazer from my son or husband, I personally gravitate to a preppy feminine aesthetic. It just reflects what I am most comfortable wearing. I too love reading the former man repeller newsletter and seeing her take in outfit building. As different as she is from my style I love her thought processes in getting dressed. Wonderful post and agree that scarves should not be discarded as they always fit!

    1. I have always admired Keaton’s flair for fashion too. But, like Leandra Medine-Cohen, I couldn’t replicate it. Both of these women have a style that is uniquely them. Plus all those belted blazers… I think you have to be very thin, or have a defined waist to be able to get away with that look. I have tried in vain over the years and given up.

      1. I loved this post because I too love this look. I realized that it’s hard for me to make it look good because I’m short at 5’2″ and have broad shoulders. I feel more like a linebacker than an elegant model in menswear. Do you know anything about the items of clothing a ‘square’ bodyshape should wear? e.g. what types of jeans, jackets, tops. I’d like to have my hair short like yours but fear I’d only look more like a linebacker then. 🙂

        1. Thanks, Frances. Gosh…I am not a styling expert… but I’d think you want to give the illusion of more shape with maybe fitted shorter jackets or tops. Not tight, just structured or tailored, nipped in at the waist maybe, and not oversized. The “ladylike” cropped blazers are trendy this year. Fitted but still loose at the same time. Does that makes sense? Plus pants that lengthen the legs, full length or cropped just at the ankle so as not to cut off your legs. I’d go for full legged pants or straight leg jeans… anything but skinny jeans. But you’d know best what looks good on you.

  2. I guess we’ve been on a similar wavelength fashionwise for a long time . I bought my first trouser suit in the early 1960s as a teenager ( black & brown stripe worn with a silky gold shirt ) I think it was the first in our small Yorkshire town too & one of my uncles was quite disparaging about it . He liked the fluffy feminine look . I remember being pleased that it annoyed him . Since then there have been others , including a light grey herringbone tweed one I loved , plus lots of jackets & trousers . I have a handful of skirts , mainly pleated now but only one dress , a heavy denim shirt dress from Toast . Some of the mainstays of my wardrobe are from the local Margaret Howell ‘ bargain ‘ shop & two of the casual jackets are from her menswear range . My square shoulders suit the shape but I always need to have the sleeves shortened . I don’t like the contrived look either & can’t bear to be all cluttered up . That Jenna Lyons shot makes me feel quite panicky & I never took to the half tuck business . I like all your outfits here but my favourite is the oversize black turtleneck one . I’ve a similar black jumper which I’ll wear to meet my old workmates this week . I think I have a similar scarf too , if I can find it in the scarf pile .
    PS Max has a couple of those caps in oilskin , which I could borrow but I look dreadful in them . Your face shape is right for them .

    1. I too have always loved the menswear look. And I have also twitched and pulled at shirts that would not fit well under a jacket or sweater. I noticed a cardigan sweater yesterday with the collar and cuffs of a silky shirt built right into it, and was quite intrigued. But I discarded it as being too much for the hot, humid climate that Saint Petersburg is usually plagued with.
      I have lots of scarves, and will not part with any of them, always sure that I will find them useful in some way. Meanwhile, I just enjoy looking at them in their rich and elegant colors.
      Thanks for this post, which if nothing else reassured me that not all good fashion ideas are for a “real woman,” and that I am going to have to admit that I also like the ease of dressing in a great outfit that is also comfortable much more than I like the sum of all beautiful parts of a fussy and awkward outfit.
      Now, back to sorting my own closet!

      1. Love your phrasing, Eva… “I like the ease of dressing in a great outfit that is also comfortable much more that I like the sum of all the beautiful parts of a fussy and awkward outfit.”
        Good luck with the continued sorting. Ah…I feel a good sort coming on. 🙂

    2. I should have mentioned Margaret Howell in this post. I know she is a favourite of yours, Wendy. She is the ultimate menswear-inspired designer isn’t she? When Elizabeth and I were in London in 2017 we visited one of Howell’s stores… in Marylebone, I think. All I know is I looked it up and we walked for a half hour to find it.
      It’s funny but while I hate wearing anything that requires too much checking and tweaking, I love a sweater around the shoulders. Partly because it can be messy and lopsided and still look right.

  3. Other than liking the clean unfussy lines of men’s wear I think men’s clothing is better made and seems to be less influenced by what’s on trend. As far as the shirt sandwich. I have a hard time with a lot of layers, but I do like a button shirt underneath a sweater. It’s a favorite combo. A couple of tips for this kind of layering: I keep smaller sized shirts to layer or I put a tight fitting men’s or boys sleeveless or tank t-shirts over the button shirt then layer the sweater. What I really can’t do is the sweater over the shoulders I fuss with it, it always feels like it’s falling off and eventually I take it off or put it on. Also tried the turtle neck layer and can’t do it either. So many things in theory are better than in practice.

    1. You’re right, Robyn. Menswear is often better made. The dress pants I own bought from Atitzia are made like men’s pants in the waist area. Such good tailoring for a mid-priced brand. I’ve never thought of layering a tank over the shirt first to keep the shirt in place. I might try that with a tight-fitting cami. They are slippery and the sweater would slide on easily. Bonus.

  4. I love the last outfit from the 70s, and the fit of your Zara jeans. I am that not into hard-core menswear styling on me but definitely prefer more boy-ish clothes than feminine ones. Basically I prefer male cuts but put them together in a feminine way or mix. Hope I am making sense :). You look fab btw in nearly all of these outfits.

    1. Good strategy, Lise. Putting menswear-inspired pieces with more feminine ones. Makes the outfit all about you. And if it’s not all about you, you won’t be comfortable. Like that shirt, sweater, and pants combo I tried. It’s just not me anymore. It needs a more casual element. Or maybe I should lose the belt and add sneakers.

  5. The top image from Pinterest on the right-jeans, turtleneck, blazer is a uniform I’ve worn this winter when I go out and about. I have to say I get exhausted by the bad wrap black gets. Three best purchases I’ve made this fall/winter are: a black leather blazer, a black sweater from Club Monaco called the Tommie sweater, it’s somewhere between a turtle neck and a crew. I get compliments on it all the time but it stays sold out, and a pair of burgundy corduroy wide leg trousers.

    1. When black is flattering on you it is great. For some of us black is a bit too harsh (my colouring is more muted, mid-toned), so it’s frustrating that often black is the only option that one can find in classic colours. What I object to is that everyone is told to have a little black this or that while on many women, especially older women, there are other neutrals that would likely be more flattering. My partner’s mother was an Italian widow with the most beautiful chocolate-coloured eyes. I always thought she would look better in chocolate brown neutrals, but alas she mostly wore black.

    2. I’d love to find a great pair of corduroy pants, Robyn. but I fear they’d be too much pant for me now. Around the waist where I have put on weight in the last ten years. Plus I’m saving myself for spring shopping. I don’t want to mess up my “five things” pledge. 🙂

  6. Always loved menswear but struggled with my basic body shape and oh, the agony of trying to get trousers to fit…my go-to will probably always be a pair of simple trousers (with pockets) and a baggy white shirt, mens-style. And brogues. Just so comfortable. My idea of hell is any kind of woman’s shirt, tailored. Your exploits with shirt sandwiches reminded me uncomfortably of the layered look, so popular in the early 70s. Shirts with huge spoon collars, ballooning sleeves with four-button cuffs, worn under tight jumper, deep rounded neckline and sleeves ending above the elbow. Then putting on a jacket/trench coat. So much damned pulling and tugging and tucking. The very origin of my dislike of skirts and shirts. (Shudders. Still…)

    1. Oh Annie, you have reminded me of those 70’s days with the blouses with huge long puffy sleeves worn under a tight short sleeved jumper with a scoop neckline ! I distinctly remember an outfit that was a black pleated mini skirt, a black puffy sleeved blouse with a huge collar and a bright emerald green short sleeved knitted jumper on top. Oh we thought we were so fashionable, thanks for the memory………

    2. I have such fond memories of those balloon sleeves with all the buttons, Annie. And a Christmas outfit when I was in grade five… 1968. One that Mum let me have early so I could wear it to the Christmas concert at school. But not before she set the buttons over about six inches on the cuffs of the blouse because I was so skinny that the sleeves just hung down to my knees. Ha. Ah, the drama when I first tried it on and looked ridiculous.

  7. Right on the same page with you! I also prefer men’s tailoring (the quality especially), and suit pantsuits better than skirts, but my approach is not as overstuffed as some of the Pinterest shots. Oversized suits, too, aren’t for me, so mine are slimmed down and add some colour sometimes (e.g., a jacquard under collar or an unusual colour to the jacket). Men’s Levi’s 501s were a mainstay of my university years (with a camisole and loose lambswool cardigan and chunky belt!) and most of my trousers right now are in a menswear pleated style with turn ups!

    I like jackets but not oversized (though admire Charlotte Rampling’s style immensely – saw her in a restaurant in Paris last year in slim black pants and simple top and a windbreaker, so the look was all about her soulful face and eyes and not the clothes!).

    I have a similar hat that looks awful on me unfortunately – too flat against my slightly long face – but you look great in that look! It adds an element of whimsy. I like it. I want to like scarves, too, but I often find I take things off that are tightly wrapped around my neck, unless for warmth – they make me feel constrained somehow.

    1. After I saw that shot of Charlotte Rampling on the runway I found all kinds of shots of her in simple menswear-inspired looks. She just looks so comfortable in what she wears. Probably because she’s comfortable with who she is too. How cool to run into her in Paris.
      Speaking of overstuffed looks…which is how I felt when I tried that “shirt sandwich”… I think that Leandra Medine-Cohen can get away with all those layers because she is so rail thin. But even so, I’d like to see her try to raise her arms with that turtleneck and denim shirt tucked into her pants, and then how much re-tucking had to take place after the arm-raising. Ha.

    1. Yes please….storing scarves and wearing scarves. I have some that must be 40 years old and I can’t seem to part with them….but when I put them on with an outfit I almost always take them off. I have them on scarf hangers in my closet….maybe I should hang them outside the closet in my bedroom and enjoy their beauty….like I have my belt collection sitting in a sectioned wooden tray on top of my dresser😂

  8. It seems to me that waaaay back in the day (early 70’s) there was no such thing as women’s Levi’s; we all wore 501’s and bought a size that would eventually fit after we sat in them in a bathtub full of hot water.

    Back then I also remember shopping for shirts and sweaters in the big boy sizes, which were a good deal less expensive than what I could find in the Junior girls’ department.

    I love the menswear look, but I get a panic attack just thinking about trying to wrestle with a shirt sandwich (shades of the many-shirted Steve Bannon). I am a great fan however of a white tee under a v-neck or a crew neck, which also saves on dry cleaning sweaters.

    I love these looks, Sue! And I sure hope you’re right about the death of the oversized blazer trend. Let us hope the same fate awaits the voluminous trouser, with the hem so long it’s a tripping hazard!

    1. Your comment made me laugh out loud, Sarah. We had to do so many things back in the day to make things fit. I’d stretch the legs of my jeans every wash. They were always verging on too short. Then there was the Javex bath to make them more faded. And the safety pins in everything to make stuff fit. Ha.

    2. Sitting in the bath, glumly. Watching the dye flow out. Knowing mum would go ballistic when she saw the result. Then wringing out the huge jeans and stretching the legs…drying them on the radiators (more dye marks) and finally trying to get into them as they had dried rock-hard.
      We had to suffer for our style back then.

  9. While I love a good layered menswear look, living most of my life in warmer climes it hasn’t been one I could pull off, temperature-wise. which doesn’t stop the longing, of course. While we were in Toulouse last week, there was a very chic woman at one restaurant we dined at, wearing a very crisp white shirt under a dolman-sleeved black sweater (hem of the shirt just sticking out below the hem of the sweater), and I thought, “Maybe I could do something like that,” because it wouldn’t be so binding with a looser arm, right? Commented to my husband that I loved the look, but since I’m committed to the only 5 new items this year I’m probably not on the hunt for a black dolman-sleeved sweater. Then I got back to the hotel and realized that the charcoal sweater in my suitcase, while not quite dolman, might work quite nicely. Have I tried it yet? No. Will I? Of course, and if it works, it just might go into the suitcase for our quick trip to Paris in two weeks.

    1. I’m glad it’s not just me who watches what other women are wearing when we travel. Last fall I stopped a women on the street (in a square, actually) in Lisbon to compliment her. She was obviously a tourist, she sounded like she might be from Scandinavia or Croatia (the Croatian ladies are so chic, I found.) And her knee-length blue linen dress, white sneakers, and cross-body bag was such a perfect look for sightseeing on a hot day. I’m going to remember that outfit when I shop for our next trip.
      Have fun in Paris. You guys are living the dream. I still feel bad that we never managed to connect when we were in Portugal.

  10. I too will wear a white tank top that is high necked under a v sweater or crew sweater. I can’t stand all the layering, though, too fussy, too constricting, too darn hot! I can’t even wear turtlenecks for this reason. And I’m highly allergic to wool of any type, so only cashmere sweaters. No draping of fabrics or sweaters around, they always fall off, and there is nothing worse than constantly checking to see if all your bits are in the right place.
    I hate most women’s blouse tailoring, except for Chico’s no iron blouses. They have a bit of stretch, which makes them nice, and they are truly no iron, great for travel. I actually prefer dresses for warm weather travel, one and done with some accessories and shoes. Some skimmies shorts and not even a slip. Oh for warmer weather!

    1. Me too, Susan. I love a high-neck tank top under a sweater. Even better than a tee shirt because… no sleeves. After our last trip to Portugal last fall I am going to look for at least one new travel dress for our next foray. I was so hot so many times! And didn’t wear several pieces that I had so carefully planned to wear. So many sos in this reply. Ha.

  11. Dearly love photo of you at University in the 70’s. I too had a charcoal blazer…loved it, don’t know what ever happened to it. Love anything you wear with your Max Mara coat, looks so fashionable and comfy.

    1. Thanks, Heather. When I bought that coat someone on here said that green was a neutral. I thought they were joking. But…wow… that coat seems to go with almost everything.

  12. I have a similar minimal menswear style, and wrestled for years with why men could do the layered shirt/sweater/blazer/(tie) when I felt strangled and constrained, like wearing an impossible straitjacket. I finally realized, duh, they don’t have to redo the whole thing every time they use the bathroom. They tuck and arrange everything once, et voila, they’re done for the day.

  13. Love this post! What i love about menswear-inspired looks is the simplicity of clean lines. That said, I look awful in shirts under sweaters; too much “boobage”! Give me me a formfitting t or turtleneck under a blazer, even better in softer colors like grey blue ir ivory, tone on tone, w trousers and maybe a little heel. This lets me feel like i can forget what I have on and go about the day or task with a more relaxed sense of confidence.

    1. Love, love, love a slim turtleneck under a blazer, too, Lisa. But these days I can’t shrug the blazer off when I sit down in a restaurant… too many lumps and bumps under it. Ha.

  14. I love the look of a white shirt under a sweater, but I always struggled with the sleeves, which made the outfit feel too confining. Then I saw the genius idea of a sleeveless white shirt with a collar. I wear one all the time under a sweater. I also have a chambray version: I took a denim shirt that I never wore because it was a little tight in the shoulders and had the sleeves removed, and now it is great under blazers and sweaters. I really like the menswear look, but often found it’s not suited to someone who is not at least a little mannish in billed. I am of moderate height and busty, and a lot of those things just won’t fly on me. I admire them on others!

    1. That is genius idea, Roberta. I think I have an old shirt that I rarely wear. I may try your idea to have the sleeves removed. Or maybe even buy a thrifted white shirt to do the same. Thanks for that suggestion.

  15. I’ve always loved tailoring. And faded jeans elevated with a well-cut jacket is a favourite look, especially since retirement and salt and pepper hair became part of my style. I understand what you mean about the faff involved in wearing shirts under jumpers – all that lining up of collars, sleeves and cuffs isn’t for me either. I far prefer a tee-shirt under jumpers, even or especially, if you can’t see the tee.

    However, my love of tailoring needs to be carefully managed because I have an hourglass shape, and a generous hourglass one these days. Slim-hipped and very tall, I am not! But long, long ago I nailed the menswear look in my 20s with the help of my dear mum, who could sew and even do tailoring. She made me a white suit with matching vest, like John Travolta’s outfit in Saturday Night Fever. It fit like a glove because she was talented and it was made-to-measure. I wore it without a shirt under the vest, and often without the jacket, and felt wonderful in it. Something about the sharp lines with my curves seemed to work really well. Ah, the memories! 😂

      1. I also like the simplicity and clean lines of menswear. What has always annoyed me is that a man’s shirt is invariably better made and for some reason are cheaper than a similar women’s one.
        I wore school uniforms from the age of five until sixteen so clothes then were mostly knock about ones with the odd dressier outfit.
        In university I lived in jeans, cords and tee shirts in summer and jumpers with stout raincoats and desert boots in winter.
        Every now and then I would feel I should try something more feminine and buy something floral or frilly but it never felt like me and they didn’t get worn. Fripperies and furbelows are just not me. I bought a floral summer dress a couple of years ago and I always feel like I’m wearing a duvet so out it goes.
        Like you I preferred more tailored and structured clothing. A favourite suit I bought was a beige/cream one with a tailored blazer and loose fitting, pleated trousers. It always felt like me and I had so much wear from it both as a suit and separates. I am also a fan of sleeveless shirts under jumpers – saves all that bumffling and feeling like you’re at war with your clothes.
        Scarves are also a favourite and I have a lot of my mother’s lovely silk ones plus a mountain I have knitted over the years and I store the finer ones in a scarf pouch and the rest go into a large plastic sealable box to go away during the summer.
        Perhaps we can start a menswear for women drive?

        1. Ruffles and fripperies, as you say, Have never been part of my style. Although I do love a white ruffled blouse with a blazer and faded jeans. I think I sighed when I read your mention of desert boots. How I loved desert boots back in the day. My sisters had the laced version of them the first time round in the sixties, a la Steve MacQueen. And they came back into style here in the early eighties and I had a slip on brown suede pair with a quite pointy toe. They probably weren’t actual desert boots but they had the same vibe.

  16. Not a big fan of menswear in the past, especially professionally, but in retirement I find I am gravitating towards the comfort of it. I always wore dresses snd skirt suits to work. I didn’t wear jeans much when I was young but bow I practically live in them (all colours) and love to dress them up. Not a fan of pleated trousers as I never had a waist to speak of so I preferred the “sheath” look and the skinnier pants. I have a ton of scarves for all occasions and also kerp them on scarf hangers. I often wear a scarf instead of jewelry. You, on the other hand, look amazing in your menswear inspired outfits. You have a great shape for it. I can also imagine a long skirts with some of those outfits. Love your blog.

    1. I have a scarf hanger and hang my more light-weight silky scarves on it. But I keep my heavier wooly or cashmere ones folded into a couple of baskets on top of a small cupboard. I rotate the ones I am currently favouring into a spot where I can see them and tuck the others inside the cupboard. I have stopped buying scarves. Because I have nowhere to store any more.

  17. Menswear has always been my best look. I first realized this in high school, when my boyfriend stopped by and caught me in my white Keds, Bermuda shorts, and my father’s worn out white dress shirt with the frayed cuffs rolled up. He said, “You look terrific in sportswear!” At the time (many, many decades ago), girls only wore pants for sports. My mother did everything in her power to get me into ruffles and pastels, but it didn’t stick.

    Today, now that I’m retired, my favorite look is sneakers, straight legged jeans, a tea shirt or tank top and an oversized cardigan. My body requires extensive tailoring to get a blazer to fit properly, so knitwear is my preference.

    Sue, you are an inspiration to me. I love your outfits and appreciate your detailed explanations of how you put them together. Thank you for another wonderful post.

    1. Thanks, Cathy. I love the sound of you in your Keds. Thank goodness my mum was not a fan of ruffles either so she didn’t press them onto me. She was not an overtly feminine dresser. I remember introducing her to the short-sleeved collared golf-style shirt in the eighties and she wore them forever after that.

  18. I’m with you too on the clean and simple lines. I absolutely hate fussing and fiddling around with sleeves, collars, waists, etc once I’m dressed and I also really hate feeling constricted.
    Scarves can either make or break an outfit. For me, they have to be worn with an air of insouciance! I once made the mistake of googling scarf knots and was bombarded by so much faff! You pulled off the sandwiching perfectly!

  19. Of course, as usual, I am still thinking about previous posts….not that I didn’t appreciate all your wisdom on being a white haired woman of a certain age who needs to keep her look edgy so she doesn’t veer into the “twee” category. So thank you for all your thoughts on dressing in a relaxed but current manner. But my real reason to write today is to ask, have you ever read the Bruno, Chief of Police series? Don’t let the title put you off. Bruno is the chief of police of a town in the Dordogne region of France. Of course there is a mystery that needs to be solved ( usually a murder) in between finding the best wine for the wonderful French meal he is concocting in his country house kitchen, with his trusty mutt at his side. The books are truly a delight. If you haven’t read any I hope you will give them a try

    1. I have heard of the books but not read any. I should definitely give them a try since we are considering a return trip to France, specifically that area which we did not visit on our previous trip in 2015. Thanks for the suggestion, Jane.

  20. I had to think a bit about whether/how much I like menswear, flip back through memory-bank closets of pants (favourite were Katherine Hepburn-reminiscent, wide-legged, cuffed, pleated, lined, creamy white fine wool) and blazers. Shirts under knit vests or with collars popping under a shetland-ish sweater. . . .And, currently, a denim boilersuit, a tweed overcoat . . .
    I’m more and more in dresses and skirts these days, though, and I can absolutely understand why older men might have drifted towards suspenders and abandoned belts. . . I’m not so keen on constraint around my waist anymore. And if I’m honest, I doubt the menswear ever suited my shape as well as it does yours. Those gorgeous wide-legged pants looked best with at least a 3-inch heel (and, of course, once they were hemmed for that length, they couldn’t be worn with flats — men have no such problem with their Oxford brogues!).
    Love you in that cap, by the way! 😉

    1. I am on a quest this year to buy only five new things and am planning to save any new shopping for spring, especially since we have a big family wedding coming up in June. But my plan for the next couple of months is to scour the thrift and consignment shops for some cool menswear. Like a sweater vest, and an oversized white shirt.

  21. I love menswear too, and enjoy seeing you in it: you wear it well.
    If I could buy something fancy – and had unlimited funds – I would want a tartan suit like one of Alan Cumming’s.

  22. So many great comments here that were my thoughts too. I copied the Annie Hall aesthetic, if I couldn’t find the outfit I sewed it. Personally to carry off the tailored men’s wear look Sue has the body for it. Unfortunately, although I’m tall I have narrow shoulders and hips! I loved the 80’s & 90’s shoulder pads, broader shoulders make your clothes hang well.

    1. Oh, those shoulder pads. I had a pair that had velcro in them that I stuck into the shoulders of sweaters and often they migrated to other parts pf my body without my noticing. Ha.

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