I Didn’t Know How to Dress Until I Was Given a Bag of My Grandfather’s Clothes

Joel and grandfather in clothes.
Joel Calfee/PureWow

When my grandfather passed away, I never could have predicted that clothing would be the thread that would connect us years after his death.

My maternal grandpa, Roland “Ron” Kessler (who my family endearingly called “Paw Paw”) was someone with whom I shared many passions—writing, art, music, reading. He and my grandmother, Rose, lived in a house five minutes down the street, but they weren’t anything like the overbearing grandparents I saw on reruns on Everybody Loves Raymond. To me, they equaled my parents or my siblings in our level of closeness. Growing up, I spent countless days visiting their house, where I played with Powerpuff Girls toys, watched Disney films on VHS, learned how to play pool and greedily chowed down on pepperoni pizza Hot Pockets. To this day, I have strong memories of that house and my time with my grandparents…but I don’t recall my grandfather and I ever discussing the clothes on our backs. Not once.

Flash forward to February 2018, when my grandfather passed away on Valentine’s Day (a coincidence my family deemed fitting, given his loving nature). I found myself standing in his bedroom, staring at piles of sweaters, button-ups, scarves, socks and more. “I’m going to donate whatever you don’t want,” my Grandma Rose told me. (I happened to be the only one who was the same size as he was.)

As I scanned the apparel, I realized that I was looking at someone’s entire life scattered across the bed. In truth, I had never paid much attention to Paw Paw’s clothing, but in that moment, I started picking out sweater after sweater, shirt after shirt. Maybe it was a desperate attempt to hold onto him, but still, I carried home those heaving bags of clothes.

Joel and grandpa clothes.
Joel Calfee/PureWow

I didn’t know it at the time, but this would be a turning point for me, style-wise. Until that day, I never really had a good sense of style, or even a personal style at all. A few months prior, when I was hired to write for a fashion and arts magazine at my college, I felt like a hypocrite when I secured the spot. Why? Because I struggled to express myself through my clothes. I felt like I didn’t know how to pair things, what risks I should take. “How do I make a French tuck?” I thought after watching one episode of Queer Eye. “Can you actually mix patterns?” I wondered as I stared at myself in the mirror, looking like a clown. Now, I was being handed a lifelong wardrobe as a launching pad. It was a gift I could have never foreseen.

After obtaining all these hand-me-downs, a few different things happened. First, I started getting more compliments on my style than ever before. People would stop me to tell me they loved my sweater or ask me where I got my brightly patterned top. “It was my grandfather’s,” I would answer, with a smile. It felt like I was keeping a piece of Paw Paw’s spirit alive.

But at the same time, I also started to understand my grandfather even better. Although I had never paid attention, his clothes spoke to his personality. Ever the meticulous man, his wardrobe was full of pieces that he kept in tip-top shape for decades of his life, indicative of his careful nature. Plus, he had a knack for finding things that were simultaneously stylish and snug, which reminded me of his love for comfort. But most notably, as my mother pointed out, he used his outfits to feel confident in himself.

Joel and grandpa clothes.
Joel Calfee/PureWow

For context, Paw Paw was diagnosed with Parkinson’s disease when he was only 55 years old. As someone who had always been a leader, an organizer and a planner, this was a huge blow. But, like everything else in his life, he took the challenge head on. If he couldn’t control this debilitating disease, then at least he could control other aspects of his life. He worked to stay in shape and combat the effects Parkinson’s would have on his body. He continued to make countless paintings, despite the tremors. And even in his final days, I can still picture him wearing those chic sweaters and dress pants. He always wanted to look his best.

These thoughts ran through my head as I entered a period of my life where I was trying to feel confident in myself and how I expressed myself through my clothing. I stopped getting so nervous when I perused the women’s section in thrift stores. I claimed my friend’s purse when she asked if anybody wanted it, instead of letting it fall into the donation bin. I bought my first pair of heels. Paw Paw had always faced his fears, so why was I afraid to dress in a way that would make me happy?

Suddenly I was styling pieces from Paw Paw’s wardrobe in ways they’d never been styled before. I took his chunky knit Gabrielle sweater from the ’90s and paired it with a large pleated maxi skirt. I tucked his geometric Calvin Klein cardigan into a pair of thrifted flared pants. I layered his button-up under a dramatic cape. He didn’t know it, but my grandpa had helped me to finally feel free.

Sometimes it makes me sad to think that Paw Paw never got to see this part of my journey. He only knew me as that little kid, playfully wearing my mom’s red heels as I watched The Wizard of Oz and pretended to be Dorothy. But even after he passed, a part of him still managed to be a part of my personal growth.

Now, I get paid to write about fashion and I’ve never felt more confident in my style. Of course, I’m always learning, and I still take risks that don’t always pay off (yes, mixing certain patterns can make you look like a clown), but I’ve finally found what I want to say through my clothing. All it took was seeing how my grandfather could let his whole personality speak through a sweater. To this day, his clothes are still a crucial part of my wardrobe, but they’re telling a different story now.

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Associate Editor, News and Entertainment

Joel is the Associate Editor for News & Entertainment and has been reporting on all things pop culture for over 5 years. Before working at PureWow, he served as a Features...