I Let My Chic Grandma Style Me for a Week
11.13.19

My grandmother used to stand over her bathroom sink and methodically dye her graying hair light brown. I would sometimes sit on the edge of the tub and watch her work, mesmerized by her rhythm. Whenever my grandfather suggested she go to a salon and place her trust (and roots) in the hands of a professional, she’d just scoff. Why waste money when she could do it herself? My grandmother has always lived at the sweet intersection of stylish and practical. She cares about her appearance—and aims to look chic, put together—but never at the expense of pragmatism. This is the sensibility she desperately tried to instill in me.

Aging didn’t rob my grandmother of this point of view, nor her beauty, but it has hindered her ability to do everything on her own. A series of injuries over the past year have made dressing and grooming independently a challenge, and now, at 89, most days she simply dons a pair of pajamas, and she’s allowed her hair to submit to the gray. But her mind and taste remain as crisp as the light in November, and instead of focusing her attention on her own appearance, she’s taken to focusing her energy on mine.

My grandmother has never once held back when it came to offering an opinion on my look. She calls my style “eccentric,” often offering suggestions and revisions the moment I walk through her apartment door. So when I asked her to style me for a week, I wasn’t surprised she was game. “You know, all the women in Iran used to copy me,” she explained when I asked, her eyes twinkling. “I was the first woman to wear three-quarter-length trousers.” I laughed, imagining my grandmother in her twenties, strolling around downtown Tehran in 1955, raving about the functionality of capris.

Since my grandmother can no longer venture far from home, she relayed her style guide to me in person, which I recorded and transcribed for use throughout the following week. At the end, I asked her, “How would you describe your style?”

“Simple,” she said, after thinking for a moment. “Simple and chic.”


Day One: A Simple Favor

Vintage Chanel dress over H&M turtleneck — similar here, Zara jacket — similar here, Spirit Halloween boots — others here

Her styling directive: “A short dress, paired with a light jacket and high-heeled shoes. Chic, elegant, and simple. Dress to impress.”

My Interpretation: I gravitate toward maximalism, so in many ways, the word “simple” can sound like a trip to the dentist to me. I decided to put my own spin on the assignment, choosing to express myself through texture and color. First, I layered a vintage Chanel dress over an old H&M yellow turtleneck, which made me feel (and look) a bit like a minion. For a jacket, I gravitated toward a baby blue sale-rack gem from Zara, which I found with my mom when I was in college. My heeled go-go boots are actually remnants of a Halloween costume! I know that’s probably not what Leandra had in mind when she forecasted the knee-high boot trend, but I digress. You can literally find these at any Spirit Halloween store.

This ensemble made me feel like the Middle Eastern Sharon Tate. I strutted into work on Monday morning with the confidence of a Love Island contestant. So many coworkers (even ones I had only crossed paths with in the bathroom), stopped to inquire about my boots. The only negative feedback I received came from the receptionist of an acupuncturist I visited after work, who explained that it was perhaps unwise to wear a turtleneck to an appointment that involved sticking needles in my body. In my defense, it was my first time trying acupuncture. In her defense, she was right.

Day Two: Your Local Politician Could Never

Thrifted blazer — another here and here, Zara trousers — similar here, vintage Burberry shirt, Dr. Martens shoes

Her styling directive: “A trouser suit, paired with a men’s button-down shirt underneath, and oxfords. Very good for cold weather. Inspired by menswear.”

My interpretation: I got a little cheeky with this assignment. After all, my grandmother called for a pantsuit but didn’t specify a full pantsuit, so I decided to mix and match two different ones. My blazer is thrifted—I think it cost about $15—and my trousers are old Zara. Instead of opting for a boring old men’s button-down, I went with a vintage Burberry find. Yes, I am wearing three different plaids here. No, I don’t intend to audition for a role on The Politician. And while I wanted to wear these Dr. Martens all-black oxfords, I unfortunately don’t own them. So I settled for my trusty matte Dr. Martens combat boots instead. I think they got the job done.

The reactions to this outfit were more mixed. (“That’s a lot of plaid,” a goateed man on the 6 train observed on my way to work. “Yeah,” I responded before switching seats.) But ultimately, I loved it. I appreciated that the lines of each subspecies of plaid didn’t line up; I think the lack of symmetry added more dimension to the overall look.

Day Three: Dumpster Dive, But Make It Fashion

Thrifted kilt — similar here, vintage Hermès cardigan, unlabeled scarf — similar here, H&M men’s puffer, Chanel shoes

Her styling directive: “Below-the-knee skirt and a matching scarf, with the colors of the outfit in it. Pair with ballet flats because the skirt is long. The perfect outfit for taking a walk.”

My interpretation: I won’t lie to you guys, I hated this outfit. Day three was one of those days when I tried five million different things and every layer made me feel more and more like the abominable snowman and less like myself. For the skirt, I ended up going with this thrifted kilt I scored for about $7, paired with a vintage Hermès cardigan worn as a top and a matching silk scarf with images of fruit scattered all over it, which I found at a small boutique while on vacation in Portugal last summer. Finally, I layered on a big black puffer, acquired last winter from the H&M men’s section, and a pair of Chanel ballet flats. I felt like Bridgette Bardot meets Mia Thermopolis, pre-makeover.

By the time I left my apartment, it looked ransacked. There were clothes scattered all over the floor and I was late to work. I practically slinked out, willing myself to either melt into the sidewalk or somehow camouflage into a surrealist backdrop that would render me invisible. Unfortunately, neither scenario came to pass. When I got to work, a team member immediately noticed my foul mood and politely asked if I was okay. “I hate my outfit,” I grumbled faintly. She scanned me quickly, clocking the conflicting patterns and silhouettes. “I mean, I wouldn’t wear it,” she told me. “But, like, it’s fine.” I spoke to as few people as possible for the rest of the day.

Day Four: Blue Jean Drifter

Her styling directive: “Street clothes—nothing fancy. Jeans, a t-shirt, a jean jacket, “jean running shoes,” no makeup. Go like a vagabond and be comfortable, with no fuss. Perfect to wear grocery shopping.”

My interpretation: After day three’s outfit disaster (one coworker DMed me and affectionately described the look as “Anne of Green Gables, but she vapes”), I was excited to get back to the basics. On day four, I threw on a thrifted Levi’s denim jacket and the perfect pair of jeans. While I did wear a T-shirt as instructed (white, Hanes), it was chilly out, so I covered it up with this old Madewell turtleneck sweater, which I desperately hope they still have in stores because it is scrumptiously soft. On top, I added a vintage Burberry trench coat, which goes with absolutely everything. I have no clue what “jean running shoes” are, but the closest thing I’ve got are these New Balance sneakers, which I’m pretty sure I found in the kid’s section. Finally, I tucked away my greasy blonde hair with a silk bandana I stole from my sister’s closet, which has the Iranian American Women Foundation (IAWF) symbol scattered all over it. That’s the key to maintaining platinum blonde hair, by the way—never washing it, just hiding it.

Inspired by my grandmother’s “vagabond” directive, I allowed my outfit to influence my behavior and go wherever the day took me. I spontaneously met up with a friend in Williamsburg after work for drinks (on a school night! Who is she?). We gabbed and gossiped, quickly moving from one bar to the next. We ultimately met up with a few more of her friends before returning to her apartment for a nightcap. We were a New York City cliché—the night felt full of possibility. I took an Uber back across the bridge at 1 a.m., feeling liberated, exhausted, and utterly myself.

Day Five: A Silver Screen Star Is Born

Gap turtleneck, thrifted dress — another here, dad’s vintage blazer — others here, Maryam Nassir Zadeh shoes, Eres socks — others here, gifted shawl — similar here

Her styling directive: “Long dress with an open neck paired with an evening shawl and open-toed shoes. Perfect for a party mood. Inspired by old Hollywood movie stars.”

My interpretation: This was my favorite outfit all week. Do you ever throw something on and get it right on the first try? That’s exactly what happened on my last day of the Grandma Challenge. It was too cold to wear an open neck, so I opted instead to layer a white turtleneck from Gap over my thrifted floor-length white lace dress. The oversized blazer is also vintage—stolen from my dad’s closet. I love how its boxy shape breaks up all of the ethereal white, a look I’ve affectionately dubbed the “wood nymph of Wall street.” For the open-toed shoes, I went with my trusty Maryam Nassir Zadeh silver sandals (I’d give this talented Persian designer my liver) and matching sheer silver socks that I found at an Eres sample sale. The shawl was a gift from my mother—I’m pretty sure she bought it on a trip to China. I planned to pin it in the front, a look heavily inspired by Mecca James-Williams’ ode to poncho season, but the wind had other ideas.

Overall, I had a ton of fun pushing the boundaries of my style and manipulating the contents of my closet in order to meet these challenges. Although my grandmother’s style significantly diverges from my own, there was something warm and nostalgic about spending a week in items tailored to her taste. It felt like sitting in a worn leather armchair with an indent from someone else’s tush.

Last Sunday, I returned to my grandmother’s house a tad earlier than the rest of my family. I wanted to show her the photos from the challenge in private; I was worried the liberties I took might irritate her and didn’t want to cause a tiff in front of my nosy relatives. I watched her flip through the images on my phone, a blank expression on her face. After a few minutes, she handed it back to me. “Beautiful,” she said quietly to herself. “Beautiful and chic.”

Photos provided by Melanie Mignucci and Iman Hariri-Kia.

Man Repeller editors endorse products we genuinely love. If you end up buying something through our links, we may earn an affiliate commission. Learn more here.

Get more Personal Style ?