Living in Generation Hoodie: An Ode to Dresses, Jewelry, and My Great Grandmother

By Stephanie Schaefer 

A few nights ago, Daniel and I went to dinner at an upscale Boston steakhouse to celebrate our first anniversary as a couple, as well as to prove we aren’t starving writers.

It was a swanky place—the type of establishment where each knife came with its own holder, the butter was served in a funky Marge Simpson updo garnish, and the wine menu boasted a $14,000 bottle of champagne.

No, that’s not a typo. There are supposed to be three zeros at the end of that. Although we didn’t order the bubbly concoction that costs nearly a writer’s salary, we did indulge in red wine and steak, a pairing as great as a classic love story. Even writers deserve to party like Jay Gatsby once in a while.

We had been planning this date for a while and I was excited to wear my Saturday night best—a black dress, heels and sassy rose gold earrings I has been reserving for a special occasion. The hostess promptly checked my coat, allowing me to show off my new outfit. To my dismay, I felt completely out of place. The ambiance of the eatery was perfectly polished, equipped with sparkling chandeliers and sleek furniture; however, the jeans and t-shirts worn by other diners made me feel like I was in elementary school and showed up to recess dressed for school picture day.

The man standing next to us waiting for his table wore a sideways Red Sox baseball cap —à la Justin Bieber—with a bright red hooded sweatshirt to match. Now I’m a huge Sox fan myself, but c’mon man, Spring Training has barely started!

As I sipped my glass of Malbec, I wondered, “Is our generation carefree and comfortable, or are we just sloppy?” I began thinking about my great-grandmother who never left the house without lipstick. Before she passed away a few months ago, my Nana refused to wear the hospital gown she was given while recovering from surgery. She made my mother put on her silk pajamas instead. Even at 100 years old, she wanted to look her best.

At my great-grandmother’s wake, I stumbled across an old photograph of her and her husband enjoying a few beers with their best friends. Although the picture seems to be taken at a local bar, everyone in photograph looks polished—the guys are wearing ties and women all have their hair done up.

Even though my Nana wasn’t raised with a lot of money—having lived through the Great Depression—the snapshot of her crew is classy and symbolizes the mindset of her generation. Had this photo been snapped today, we would have seen a whole lot of baseball caps and leggings (filtered with an Instagram setting, naturally).



Recently, the Huffington Post published a relative article titled “7 Things People Dressed Up For In Our Grandparents' Day,” showcasing snapshots of generations before us. It’s hard to believe that people once put on their best attire for grocery shopping and traveling, when today we don’t even change out of our hooded sweatshirts for a night out on the town.

Although I’m thankful that women today aren’t expected to sleep in curlers or wear nylons in 80-degree weather, I can’t help but think that a little more dressing up wouldn’t hurt us. I am a firm believer that the way we dress on the outside often reflects the way we feel on the inside. Call me a girly-girl, but there’s a red dress hanging in my closet—my own personal Super(wo)man’s cape—that makes me feel like I can conquer the world. 

As Coco Chanel once said, a point that my great-grandmother proved so well, “Dress shabbily and they remember the dress; dress impeccably and they remember the woman.”

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