I Dressed Like My Grandma & Here's What Happened

Winter is coming. For me, this means my wardrobe is slipping further and further into New York City-stereotype territory ahead of the wintry parade of black coats and en masse seasonal affective disorder. There’s definitely something comfortable about rocking a uniform of grays, blues, and blacks in the cooler months of the year, but I do start to feel a bit, well, blah.

I wanted to disrupt my routine, but instead of looking for inspiration from famous fashionistas, I turned to my own family. My maternal grandmother, Yvette Twohey, was quite the snazzy dresser. She died when I was 16, after a decade-long decline from frontotemporal dementia, so I don’t actually have many memories of her fabulous fashion sense. It just seems like something I’ve always known about her. From photos. From family stories. From the piles of rad vintage clothes my sisters and I inherited from her.

So I asked my mom to send me old photos and got on the phone with her and her sisters to hear their recollections of Yvette’s outfits. “She loved clothes and she did it on a shoestring,” my mom said. “Sometimes, she would lay a bunch of things on the bed and try them all on. She cared about the look, not the label.”

I was inspired: I would dress for a week like my grandmother, and see if my style got a revamp.

The Experiment:

Obviously, my androgynous style is extremely different than my grandma's was, so I needed to prepare. As I set about putting together a week’s worth of Yvette-inspired looks, I followed her throw-it-all-on-the bed methodology.

I’m lucky to own a few garments that actually belonged to my grandma. From there, I supplemented with other vintage pieces I already had, plus some strategic thrifting to fill in the gaps. Here’s what I came up with.

Day 1: 1940s Teenage Dream

This photo was taken in the late 1940s, probably when Yvette was 16 or 17 years old. It’s hard to make out the exact details of her outfit, but it seems consistent with the modest A-line dresses that would have been popular at the time. I took to the thrift stores and found something similar, which I paired with white tights and oxfords.

This outfit wasn’t far from the kind of thing I wear in the summer, sans tights, but it definitely felt like playing dress-up to put it on in late November. (Apparently, the femme parts of my queer heart go into hibernation by the first frost.) Although I felt a bit goofy, I did get lot of compliments. I attended a freelancer meetup (networking dinners for women creatives are probably why compliments were invented) and multiple people told me I looked “adorable.” That was nice. I decided I liked playing dress-up.

Day 2: Plaids n’ Neckerchiefs

I have to admit, I have no idea what’s happening in this picture. It’s 1950 and my grandma (far right), grandpa, and another couple are participating in some genial chin-trimming ritual?

Regardless, I love the jaunty little neckerchiefs both women are wearing, and it seemed like a simple style to replicate. I’d heard from my mom and all three of her sisters that Yvette loved bold colors and loud prints, so it seemed fitting to celebrate her loudness with a silk scarf and plaid shirt.

I didn’t interact with many people on neckerchief day. Work was quiet, and I went straight home afterward, so I didn’t hear any hot takes on my Yvette-style accessorizing. But I did feel fancier than usual. A little touch of vintage glitz can go a long way in shaking up the winter wardrobe blues.

Day 3: First Communion

This photo was taken in 1958, when Yvette was 27. She had three kids by the time she was 24 (she would have a fourth a decade later). Here she is celebrating the first Communion of her oldest, my aunt Carole, with her mother.

I think she looks so cute and put together in her fitted skirt suit. I have a cropped jacket that belonged to her, so I wore it with a straight skirt and low heels. A note on the shoes: my badass little sister crafted these animal pieces for me a few years ago. (I rarely wear heels, but when I do, I make sure they have adorable beaver faces on the toes.)

To be real, this outfit was pretty uncomfortable. The jacket fit tight around my ribcage (Yvette was tiny) and the heels were very pinchy. I got some nice compliments from coworkers, but all in all, I felt out of my element. At the end of the day, I couldn’t bear the thought of walking back to the train in those shoes, so I swapped them for the Keds and socks I had in my bag. I took off the jacket in favor of a sweater, and my fall coat isn’t exactly period-appropriate. The outfit fell apart.

First Communion hot mom status not achieved.

Day 4: Bridge Queen

By the mid-1960s, Yvette was rocking a full bouffant. I don’t have nearly enough hair to attempt that, but I was able to find a fur pillbox to add some height and pizzazz to the top of my head instead.

My mom remembered how glamorous her mother looked as she headed off to bridge parties during that era. Yvette loved planning what to wear to social occasions, and as my mom said, “she did it for herself.” Planning her outfits was a powerful form of self-expression.

Although this outfit fell further from my usual style than any so far, the whirly skirt and gold sweater top were surprisingly fun to wear. Because of the hat, this ensemble also felt more visible. The finer points of my Yvette looks had been obscured by my outerwear whenever I’d been out in public, but the hat definitely stood out. Even on the New York City Subway, where aloofness reigns, I caught a few people stealing glances. I went to a dinner party after work, and one of my friends called it a “jaunty chapeau,” which I liked very much.

Day 5: Shoulder Pads for Days

On the fifth day, I wore another of Yvette’s jackets, one with pretty epic shoulder pads. I added some '70s polyester prints and glitzy earrings to complete the look. This wasn’t the most ambitious of my Yvette styles — mixed prints are already pretty standard for me — but I enjoyed adding some extra color and oomph.

Day 6: Holy Snake Gown!

Here’s Yvette on her way to a party in the early 1970s. I wasn’t able to find a leopard number like hers, but I do happen to have a floor-length snake print gown from the same period that belonged to my great aunt (Yvette’s sister-in-law). So I wore that.

This was the most ridiculous outfit of the week. I don’t think I’ve worn a full-length dress out ever, and certainly not a polyester snake print one. I’m short, so this dress was too long on me, which meant I had to hold it up to walk anywhere. I was constantly getting tangled up and tripping over myself. Real cute. That said, it did feel almost subversive to wear something so billowy and odd.

Day 7: The Polka Dot Disco Suit

Without question, the polka dot jumpsuit is the piece de resistance of this whole project. This 100 percent polyester garment features a halter-top and bellbottoms, and I am its happy owner. Yvette wore this to her in-laws’ 50th anniversary party in 1977, when she was 46 years old. I love that my grandma was still getting down in bold get-ups into her forties and beyond.

My aunt Carole observed that while most people’s style tends to get stuck in a particular decade of their youth, Yvette kept evolving with the times. There’s nothing wrong with finding something comfortable and sticking to it — if anything, I probably have more in common with the women of her generation who exclusively wore bag-like house dresses by the time they turned 30 — but I do admire how my grandmother defied expectations about age and self-presentation.

I loved wearing the jumpsuit around all day. I felt absurd, but at the same time, unspeakably sexy. I went dancing, and the jumpsuit was actually quite comfortable and great to move in. I jumped around and felt like a damn superhero.

My Conclusions

It will be a relief to go back to the simplicity my normal routine, but I’m glad I spent the week channeling my grandmother’s fashion sense. In talking to my aunts and researching vintage looks, I felt closer to Yvette. That said, I want to be real about some of the less positive things I learned.

Several of my aunts said that thinness was part of my grandma’s identity, and that she probably put pressure on herself to maintain the tiny waist she so liked to accentuate with fitted jackets and skirts. It’s hardly revelatory to point out that the world contains a veritable crap-ton of messages about how bodies should look. My grandmother wasn’t immune to that.

At the same time, fashion was a genuine creative outlet for her. She loved to put on a show. I’m a little more comfort-oriented and androgynous, but I can certainly appreciate the ways she slayed in neckerchiefs and bold prints.

I may just break out the polka dot jumpsuit in February and light up everyone's night yet.

Images: Molly Jean Bennett