Small Bite 002: Recreating Jennifer Grey's Early 1980s Outfit

Tumblr, denim shirts, and Belgian loafers.

Nov 09, 2023

Editor’s Note: Welcome to Small Bites. What I’m not entirely sure what Small Bites will entail, it will begin as a place to ruminate on something that may not be fully-fledged out and/or something that doesn’t command a full 1,000 words dedicated to it. A place to inspire some conversation in the comments. Will it remain that? Perhaps. Could the name change at any given moment? Again, that’s a possibility.

I don’t know many 36-year-old dudes who still regularly scroll Tumblr but that’s just the cross I bear. It’s not often I find myself aggressively scrolling back as I trudge through hundreds of vibe pics, but I found myself absolutely gasping for air when I saw this:

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But I didn’t see this version of the photo. Because it was simply a screenshot posted to Tumblr, it was grainy, cropped, and showed zero of her face. All I had to reference was the fit itself (until Google Image Search intervened).

As someone who knows very little about Jennifer Grey’s body of work outside of Dirty Dancing and Ferris Bueller, she’s now a person who’s reached levels of respect that I find hard to describe. This outfit isn’t a coincidence or an accident; it’s a lens into the soul of someone who gets it.

The barely-buttoned tucked-in denim shirt. The oversize light leather jacket. The (velvet??) green pants matching the velvet green Belgians. Again, gasping for air, etc. and so on.

My brain went to a place it often goes in these situations: “How can I recreate this fit with what’s currently in my closet?”

Here’s what I came up with.

The Shirt: AYR’s The Alpha ($175)

I’ve famously said this shirt “gives pottery” and I’ll stand by that. When I was gifted an AYR denim shirt last year, I wore this thing into the ground. And when I made some ruthless cuts to my closet during a pre-fall cleaning session, it absolutely made the cut.

The Pants: J.Crew’s Giant Fit Chinos ($98)

J.Crew’s Giant Fit Chinos have been celebrated, criticized, and everything in between. One night as I trudged through a Unisom forest, I found myself perusing them only to buy a pair in a color that’s no longer available: Plum.

Are they baggy as hell? Yes. Did I cuff them to reduce the feeling of how much fabric was covering body? Also yes. And am I completely used to them now? Uh-huh.

The Shoes: Belgian’s Mr. Casuals ($675)

Prior to my wedding, I knew I was going to need some loafers that made me feel invincible. While I got my Belgian’s before their price increase, it was still a purchase that gave me a lot of hesitation. Until I wore them and now I plan on keeping and caring for them for the next 30+ years.

Of course, people will point to the less expensive option, Del Toros, but I can’t recommend them for two reasons: (1) I’ve never worn a pair and (2) I feel like their entire business model is just offering a less expensive version of a shoe which feels icky to me? Or maybe I’m just a Belgian loyalist because I’ve fallen so head over heels for mine. That’s probably it.

The Jacket: Engineered Garments LL Jacket ($672)

And now for the aspirational as I truly own nothing that resembles this in my closet. This upcoming Sunday, we had Timothy and Chase from Canoe Club on Retail Therapy. While perusing the site around the same time as I was looking for a jacket alternative, I stumbled upon the jacket above. While it’s not an exact dupe of Jennifer Grey’s jacket, I think it modernizes the look in a way builds a case for buying the jacket rather than the other way around. Please note: I have no idea what I’m talking about when it comes to styling.

Final Tally: $1,620 — Dammit.