A commenter named Katrina thought this question would be a good follow-up to my recent query about things you’d never wear, and I agree. As for me, I’d say that every denim trend ever has seemed wrong to me until my eye got used to it, from those (I think) Guess high-waisted, pleated, baggy numbers we all went for in about 1979 to, more recently, flares and skinnies and high-waisteds. This Brooke Shields ad for Calvin Klein is the first time I was ever sold on a denim trend the moment I spied it, so great was young Brooke’s spell on a young me. And you?
Cat-eye glasses. Once I got past having to wear them because that’s all there was when I was a kid, I swore I’d never wear them again. I’ve had tortoiseshell cateyes, and now red cateyes by Max Mara. A pair of baby blue ones caught my eye a couple of months ago. Maybe they’ll be next. I think they’re fun.
Leggings. I always thought women who wore leggings looked like they’d forgotten to put pants on, I still do. But eight years of living in a Rocky Mountain resort town and becoming an avid skate skiier killed my never leggings vow. I’d never wear them in a city (there’s that never again) and still mostly wear them for outdoor sports, but I do like how they look and feel. I won’t buy leggings with less than 20% lycra, and have found the best ones have 25-30%. When I wear compression leggings around the house to help my tired muscles recover my husband is very appreciative. He may be old, but he’s still a guy.
Leggings with pockets: game changer.
Birkenstocks. Actually Andrea Linnet made me desperate for a pair back in the early days of Lucky but she was juuuust so cool and could pull anything off. Before that, they were a hard no. Still took me till 2017 to pull the trigger on a pair and then 6 months later bought the same style in the molded plastic which I love almost 100x better. Total convert!
Yup Birkenstocks too. Pulled the trigger again in white patent last summer.
Same here: Birkenstocks! Then 8 years ago I bought a black pair “to try out” for my NYC lifestyle and I was hooked. A couple years later I bought white for my summer version. Now I also have tan suede for my “casual” look. Ha!
My knees haven’t seen a short skirt since the 90s. Camouflage anything – still a hard nope. I have always loved Birks and now own a veritable wardrobe of them (“house” Birks, “fancy” Birks…). I used to wear my grandmother’s fur coat and it was truly warm…
I still doubt that I would wear Birkenstocks. They just remind me of old hippies. Of course there is nothing wrong with that, but I tend to go in the opposite direction.
I do own Uggs, sometimes wear thongs (flip/flops) though bad for your feet! I would wear a jumpsuit. I wish I could find High waisted flares in my size. Alas though I used to wear Calvins in a size 10, I am a 67 year old size 16 now!
But have you tried metallic pink patent leather Birkenstocks? Totally not hippy in any way, old or less old
Culottes! I spent my entire life hating them with a fiery passion then went to Japan where it seemed like everyone was wearing them. 2 weeks later I was converted (they’re SO much easier in summer than a skirt). I also v much want a pair of clogs, which I never imagined would be a thing I’d say. I lay the blame for that squarely at your feet, Kim! Sadly they’re not much of a thing here in NZ yet and I haven’t found any I can try on in person, and am hesitant to order online. Although I just found Lotta clogs and they seem reasonably priced, so maybe less of a commitment if they don’t fit quite right?
Love my Lotta clogs. I initially purchased a much more expensive brand and found the sole to be a teensy bit too narrow for me to walk without falling off the clog and spraining my ankle. The Lotta clogs are the better option if you’re a klutz lime like me.
Lottas are wonderful. Take a chance!
I said Never to sneakers (except for the gym) until about 2 years ago. Now I own 3 pairs, and each purchase has been inspired by pairs I’ve seen here. At least one pair is exactly the pair you featured. Feature some new ones, as I need at least one new pair, please.
Born in 1966, and it seems I’ve seen everything go out of style, then come back in again. I swore I’d never wear a jumpsuit again – but I tried one on yesterday…
Leggings. I just don’t care for them–EXCEPT for the Spanx faux leather leggings. I love them.
I never thought I’d wear a jumpsuit, but now I own two of them!
I bought a jumpsuit last year: sleeveless black jersey, with flowy cropped bottoms. I love it, except for the part where I have to get fully undressed in the bathroom.
Button down shirts with collars. Somehow I just thought they looked really bad on me. Then about two years ago I tried one on and realized I looked kind of fabulous, both polished and, if I do say so myself, a little sexy. Now I wear them all the time.
PS. Wondering if I’m about to cave on high waisted jeans. I loathe them, I’m pretty sure, but lately I sometimes think I might at least try on a pair.
Jeggings!! As god is my witness, the ones that old navy makes are miracle comfort pants. And people are always surprised to discover they are, indeed, jeggings. I live in them.
Huh… I feel my anti-jeggings resolve waning just a bit.
Do they have a name? Just Old Navy Jeggings? Thanks!
Old Navy Rockstar Jeggings forever!
The other thing I love about the Old Navy Rockstar jegging is that they come in Regular, Tall and Petite sizes from 0 – 20. And many different washes and styles. Waiting for them to put out one with a bit of a boot cut.
Birks for sure. HATED them in my 20s/30s, but after seeing them incessantly on a trip to NYC last year and trying on the Gizehs, I wore them shamelessly from there on out. Still can’t bring myself to wear Uggs, but I get their appeal and am a little less twitchy about it.
Cropped pants. Being tall, I was forever trying to find pants that were long enough, so I wouldn’t get teased for wearing high water pants flapping around my ankles instead of skimming the floor. So when I saw pants deliberately ankle-length or higher, I thought no way. I’d look ridiculous. But now I love them — they make pants shopping so much easier!
OMG, me too! Teased mercilessly for my “floods” as an adolescent so would not even consider cropped pants for decades of adulthood. I am reconciled and, indeed, pants shopping infinitely easier and the better to show off fab booties!
Birks, Uggs, and blue nail polish.
High-waisted jeans. I do worry about the pancake butt issue but I like how they vacuum up any sort of goo around the waist area.
Like many I thought I’d never wear uggs or birks but I have more than one pair of both. But when I was younger I thought I would never wear skirts or dresses. And then I discovered that I could wear them with sneakers and oxfords etc and I wear them all of the time. The only pants I wear now are leggings, sweatpants and jeans.
I’ve always been pretty aware about what I like and what works for me, so as a general rule, my answer would be nothing! I do have plenty of fashion regrets, but it’s more about quickly tiring of a trend rather than wearing something I swore I wouldn’t!
I never thought I would leave the house without makeup but the older I’ve become, the less I wear. Still won’t leave without mascara and something on my lips tho…
Navy with black. White with cream. Jeans with any kind of a flare at all.
Leggings and denim jackets. I wore both heavily in the 80s, so when they came back around I was firmly against them. I finally caved and bought a denim jacket a few years ago, but for some reason it doesn’t get much wear. Leggings, on the other hand…I’m a bit ashamed to say that they’re literally all I wear these days when I’m not at work. Casual ones for lazy Saturday mornings, nicer faux leather ones for Saturday night dinners…I’m all in. At least I’m not pairing them with the same loud neon graphic patterned oversized sweatshirts I did 30+ years ago. Progress…haha!
Nothing. I’m a Forever Tomboy.
Uggs. For years I thought they were ugly and ridiculous. Then I tried them and learned how warm and comfortable I could be, even in the dead of winter. They won me over.
Also Uggs (heaven help me). They are the only thing that keeps my feet warm on long dog walks in Central Park. They are so comfortable, I want to wear them all the time.
Ha! I begged for those jeans. My parents made me save up because they were like $45 I think 😂
So many things..
But definitely many denim trends. Never again the hi waist..etc.. I was wrong.
In fact the only thing I haven’t reconsidered is scrunchies.. my 14 year old wears them..wtf!!!
I have failed her somewhere..
Lol. Scrunchies. My 19 y.o. niece and all her peeps wear them. They are having a moment for sure. I have a new fabulous collection but have very mixed feelings. And yet they feel so good compared to other options.
I pull my hair back in a “bun” when I exercise and my hairdresser person told me to use scrunchies rather than coated elastic bands because scrunchies are the only hair bands that don’t break hair. It’s hard to ignore that piece of advice when you’re old and your hair is thinning seemingly before your eyes!
Uggs (as slippers only), Birks, Tevas––all shoes and I wear all of them for practical reasons. My new leather jacket even though it has taken me literally years to come to terms with that desire. Still hold the line at fur even though I have a mink coat sitting in my coat closet that my parents bought me in 1985 at Fredrick & Nelson in Seattle. I wore it once to a Broadway opening and have carted it around ever since out of duty and obligation and sheer guilt for only wearing it once.
Booties with a dress/skirt. When the trend started, all I could think was what a great way to make your legs look like Stumpy McStumps. Now, I do it, occasionally.
Born in the 60’s also, I also remember the Brooke ad for CK well. “Nothing comes between me and my Calvin’s” … my friends and I considered that – does she mean she doesn’t wear underwear?? ewwwwwwwww gross! (that was our reaction!) but loved the jeans
1. Uggs here too. I resisted for many years but then I was given a pair as a gift. I never looked back after my initial wear. Since then, my new quest to buy vegan only has led me to Pawj boots as a cruelty-free replacement for my Uggs. They’re awesome, really well-made and warm. I’m wearing the short boots and their slippers pretty much daily with the wintry temps.
2. Basically anything that constitutes athleisure. My younger self couldn’t fathom wearing anything resembling the clothing and sneakers that I wore in high school gym class. Yet, my current SAHM lifestyle and my growing desire to be truly comfortable as I age, makes me thoroughly enjoy this trend. However I try to keep the look neat and spiff, as Kim likes to say.
In the 80s and 90s, non-skinny jeans (though we called them “pegged” back then, I guess because we had to sew them that skinny ourselves).
In the early 00s, skinny jeans! (now that I had become an exclusive wearer of bootcuts).
And actually… when I was younger I thought animal prints (and leather pants!) were something only older ladies wore. Now I’m a GOACA (52) and wear them. Hmmm…
By the way, Brooke briefly went to my elementary school! I had her sign my yearbook…
Birkenstocks. They used to embody the patchouli wearing Dead Heads that I thought were lame as hell in college. Now, in summer, you won’t see me in much else. Patchouli is still gross, though.
Clogs (of all kinds) and Tevas (though at least they are flatform). I never, ever thought I would wear either, let alone write about them in the context of a post on fashion!
Skinny jeans. When they first became popular, I felt very strongly that my legs would look like a pair of overstuffed kielbasa perched on 2 slimjims… this may still be the case, but I have gotten used to them!
Sneakers! Since Junior High I’ve pretty much avoided wearing them unless exercising. Over the last couple of years I’ve surprisingly acquired and been wearing about a dozen pairs (Supergas, New Balance and Converse). I still prefer shoes though!
Growing up in Western PA, where the first day of hunting season was actually a school holiday (and I was—and still am—very much anti-hunting), the idea of wearing camo was a no-go for me, but now I can’t get enough of the stuff. I own two pairs of camo pants, several camo tees/shirts, a camo blazer, etc. It’s surprisingly versatile!
Yeah, fur. Most of mine is vintage in the form of trim on old coats or sweaters, though I have a few rabbit fur vests. I just started to think if you were leather shoes, it’s not really different. But that’s probably terribly un-PC.
As a former Goth chick, I never thought I would wear clothing in any color other than black.
I’m still pretty firm on the No Headbands rule, but mainly because they give me headaches. I like to look at Fair Isle sweaters, but I never want to wear one again. Otherwise I have relaxed a lot of my strictures, starting with Birkenstocks. The most recent concession is I bought a lined wool midi skirt (Talbots) from a vintage shop. Amazingly, it does not look frumpy at all.
Skinny jeans or leggings. Gold jewelry.
Capri pants. I remember seeing someone wearing them and my friend and I laughing at how silly they looked.
Oh, yay! Thanks for considering my suggestion! Here are my answers:
– high waisted jeans
– sneakers when not exercising or playing sports
– heels with jeans. I wear them with straight cut or boyfriend jeans, but weirdly still can’t bring myself to wear them with skinny jeans.
– designer shoes. I’ve always thought paying that much on things you’d trod the ground with was dumb, but I own a few luxury brand shoes already. Sigh.
Skinny jeans, leggings, Birkenstocks. All are now in my regular rotation. I even wear Birks with socks (but only in the house for warmth. I secretly like how it looks though).
I wore Birks with socks alllll winter in college. When I wasn’t wearing combat boots. Ah, the 90s.
I’m reading this looking down at my Boston Birks with socks. I never thought I’d see the day … but I love them!
I’ve now lived in Portland, Oregon long enough that I have come to see soft shells (like a North Face jacket) as acceptable “formal” outerwear. I NEVER thought that would happen.
Yup…Birks. I remember making fun of people wearing them and now I have 3 pairs. Once you walk in them it’s all over. Plus I have long narrow feet and skinny legs and I like how they make my feet look wider and balance me out visually.
My first thought when seeing the photo of Brooke was remembering how desperately I wanted to wear those jeans. My grandmother took me shopping at the now long-gone, six floor department store on a seek and buy mission. I was so proud of fitting into those jeans even if the fit was tight and not cut for my curvy hips.
Wrinkles (on my face, never on my clothing). Always imagined I’d go for surgery but aged out of that thinking. Otherwise there’s only one item on my no-wear list (fur) and firmly it remains there.
same here. cannot imagine wearing fur ever.
as a teen & beyond I never thought I would ever wear gold jewelry, although I like a more matte finish.
Birkenstocks! I remember the first time I saw them in the mid 80s, thinking they were caveman shoes!
and now I have several pairs.
I was born in 64 too, so I know all about Brooke’s spell.
Ditto to Birkenstock’s! I grew up in Hippie Country, Portland OR in the ‘80s. All my moms friends wore them and I never would have even considered them.
Now my white Arizona’s are my favorite shoes. <3
Navy. As a Californian born and bred in black clothing transplanted by work to the Midwest and then the Northeast, I associate the color navy with midwestern frump and DC and New England prep. Now that I am a leached-of-color girl of a certain age, navy is far more flattering than black, which appears too harsh and…aging?
I used to give a lecture to medical students entitled “Leggings Are Not Pants” but here I am, sitting in my academic office, wearing a terrific pair of black “dress” leggings that have a subtle damask polka dot.
Combat boots. After wearing Dr. Martens for most of the 80s, I have always felt girls of a certain age look rather desperate in them now that they have made a comeback. (Besides, they are nearly as well-made as they were back in the day, IMO.) I opted for the Frye Veronica Combat boot for it’s grown-up cool factor and have worn them non-stop for months.
Uggs. When they first became popular, people were so fervent that it felt like a cult. It brought out my oppositional nature. I do a lot of yoga though, so I was convinced after watching women wear them to class (I became jealous of the ease of changing shoes). I’m not a winter person, so they have become a lifesaver. Skinny jeans. I thought never, but as Kim said, gradually my eye seemed to change.
turtlenecks. especially as a GOACA with, as my (younger sister says), an ” (explitive) perfect neck” (seriously. sorry but it’s true. i’m 54 and the miracle of pilates is…i love my neck, lol) and besides…my mom lives in them, lol. but. i cannot deny that they have that clean chic-ness and they look great on girls with curls…so i haven’t pulled the ripcord yet, because they still make me feel like i’m choking to death, but i am flirting with the notion…
The uggs thing is really interesting. I’m from Australia – the home of the ugg – and no one wears uggs outside the house. We wear them as slippers.
But I was in NYC in December, I marvelled at how every third woman was wearing uggs. Outside! On days it might snow! Blew my tiny mind.