I didn’t always think of clothes as stories. They were utilitarian objects, to be worn and tossed in the hamper until next time, rarely fulfilling a higher purpose. But as my relationship with fashion has changed through thrifting, I’ve started connecting more of my clothes with specific memories, places, and people. Not every piece I own tells me a story, but here are a few that do talk:

1. The Tie

Truth be told, I don’t wear ties often. My casual workplace, coupled with an expanding sense of what constitutes “dress clothes,” means I’m normally at the Kennedy Center sans-tie. When I do decide to fiddle with a full Windsor, though, it’s using this one: a hand-me-down from my late grandpa.

The material is definitely not silk, the pattern’s nothing to write home about, and it doesn’t scream fashion! — but that’s precisely why it means so much to me. My grandpa was a quiet ex-farmer with a Midwestern work ethic, and this secondhand tie always reminds me to talk less, check my work, and pay attention to the weather.

2. The Blazer

Speaking of dress clothes, I’m indebted — like, fully indebted in the financial sense — to this guy:

I might wear a funky geometric sweater to a steakhouse, but there’s one place I won’t break dress code: job interviews. I go simple, I go approachably dressy, and I always go blue — my safety color. I lay credit for my current job squarely at the feet of the above blazer, a nicely textured and well-fitting blue number from (where else?) a Goodwill in the DMV. 

3. The Jacket

A consequence of endlessly listening to Neil Young and browsing Instagram for 1960s fashion inspo is that every now and then I’m convinced my life in DC is an illusion, and that I’m actually a rock star out in Laurel Canyon. Hence this jacket:

This was another local Goodwill find, nabbed from the behind-the-counter section, where the pricier, curated pieces live. Still incredibly affordable, soft and supple, with that lingering ancient smell you only get from leather that’s seen a few packed clubs. I haven’t learned to play the guitar, but I did wear this jacket to my partner’s birthday party and felt mighty, might cool. It’s a start!

4. The Pajamas

Pajama pants? Thrifted? Believe it.

As a diehard fan of a soccer team that plays many time zones away, I wake up far too early on far too many Saturdays to watch them lose. Might as well do it in comfort, courtesy of Goodwill. These all-over print pajamas let my fashion do my cheering for me on those days when even coffee won’t get me awake enough to shout at the TV.

5. The Pants

Only in the last month have I started making trips to thrift in-person. With heightened (and sensible!) public health protocols in place in Goodwill stores, I was unsure how I’d feel thrifting without dressing rooms. Guesstimating clothing sizes never goes well for me, and imagining how silhouettes and prints will look out in the wild is an imperfect process at best. I grabbed a pair of slate blue slacks and hoped for the best.

It was a momentous occasion. They fit perfectly. Turns out mentally scrolling through every pair of pants you’ve ever worn is a pretty good way of imagining how a thrifted pair will fit… It’s a tiny victory, but this Goodwill find marks my successful entry into the world of “don’t try before you buy.” We’ll see how long this rush of bravery lasts!

About our Guest Blogger:

Seth of @wholemilkthrift is a radio producer with an abiding love of vintage varsity, fur collars, and anything made of linen. Follow him to learn how thrifted finds can subtly elevate business dress codes. He thinks all men need to thrift. Like, now.