How to Look Incredible in Your Grandad’s Clothes

There’s no escaping my mother’s scathing jabs at my light-wash mom jeans every visit home. The irony of this recurring exchange never fails to amuse me. Does my mother take pride in refraining from the mom jeans, the mark of style in my generation and what clearly indicates a lack thereof in hers? Or is this part of the Boomer generation’s widespread adoption of younger trends like athleisure, leather goods, or big sunglasses? Either way, Boomer- and Zoomer-chic have reversed their target audiences. 

It would be generous to dub my mother’s combination of a graphic tank top, gathered sweatpants, orthopedic sneakers, and scrunchie for elementary school drop-off an “outfit,” but it bears remarkable semblance to certain Zoomer style icons’ recent ensembles. Billie Eilish takes the concept of orthopedic sneakers to the next level, cartoonishly standing in green Balenciaga sneakers almost half the size of her body. Any viral TikTok dance video features three smiling Zoomers sporting their best sweatpants and a carefully arranged messy bun. Eilish’s sneakers have the neon appeal that my mother’s lacked, and the TikTok girls put a little more effort into their makeup than my mother used to do before carpool. Nevertheless, the Zoomer generation definitively co-opted the off-duty Boomer look to suit its own needs.

On the other hand, a few weeks at home proved how well the older generation has learned to adopt rapidly changing trends. An intimidating posse of Boomer-aged women sporting their latest Lululemon leggings greeted me at a group-exercise class. I felt like a washed-up grad student in my pit-stained Yale Athletics t-shirt. 

When I visited my grandparents, I complimented my grandmother on her new quilted beach bag. She’s come far since her Merrell sneakers phase. At Christmas dinner, my mother easily outdid my stale wool sweater, sporting a chic leather tank top that bordered on edgy without reading full-on biker gang (a look I wouldn’t recommend she try). Major brands know they can riff off younger trends and resell them to an older audience. 

 This fashion osmosis runs in both directions, with Zoomers adopting styles from an earlier generation. I used to critique my dad for wearing pleated pants that were loose behind the knee—a telltale sign of an out-of-touch Boomer. Now, on a quick scroll through Instagram, I’ll see countless influencers championing the same style—usually in plaid, and usually with a neon accessory to give the look some edge. Mom jeans and mid-calf dresses fall into the same category. My grandmother’s dowdy floral pieces used to give me severe secondhand embarrassment. Now, Zoomers younger than me pride themselves on thrifting dresses like hers. What prompted the switch? Do we Zoomers steal our dads’ knit sweaters to recapture the parental affection so abundant in our childhood? Do Boomers adapt to younger trends in an attempt to relate to their “zooming” descendants who are too busy to slow down and enjoy a nice family dinner? Maybe these reversed trends reflect an inter-generational desire to connect and relate. Or maybe we all just enjoy the comforts of large, chunky sneakers.

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