Where Have All The Jack Spade Bag Boys Gone?

Remembering an aughts icon

Sometimes the retro cycle can surprise me. Like I wouldn’t have thought people would be asking if they needed to buy a pair of bootcut jeans because they saw Kendrick wearing them when he publicly executed Drake at during halftime at the Super Bowl this year. I know people were trying to say bootcut was going to make a comeback before everybody felt they needed to have to have a take on Serena Crip walking to “Not Like Us,” but that just felt like a whisper campaign by Big Bootcut. Not that there’s anything wrong with that particular cut of jean; I just didn’t think it was due a comeback status. But I’m wrong more than I will admit, and that’s good because it reminds me that there’s always room to dream about what could come next, and in my sick little mind, I keep hoping “The Kids” are going to start walking around with Jack Spade messenger bags again.

I started thinking about the once-ubiquitous canvas bag last year when I was looking through a box of stuff I have stashed at my in-laws place in Connecticut. Wedged in the bottom was one of my own old Spade bags that you used to see on every other shoulder when you got off the F at Broadway-Lafayette, a symbol of some status around the same time when city dwellers started killing their feet by wearing Red Wing Iron Rangers to work, and “creative” dudes with salaries in the low six-figures held out that their Blackberry would outlast the iPhone. My bag had been retired for well over a dozen years, and was mainly used for holding old paperwork and assorted ephemera, but I looked at the thing and started to feel mad at myself for abandoning it when I decided to just stick all my stuff in a wrinkled tote somebody gave me for free. Now that it’s been a full decade since all the Jack Spade stores closed and the brand was brought in under the Kate Spade label, I keep bracing myself for the teens to start using them. No doubt after going through boxes of their dads stuff from the 00s and thinking, “This looks old and cool.”

The Jack Spade bag first started getting notice at the end of the 20th century. GQ mentioned Andrew Spade as “the husband of handbag queen Kate Spade…getting into his wife’s business” with the canvas messengers and duffels alongside an illustration of the “Status man” of the time in a pair of tight Helmut Lang jeans, a Comme des Garçons shirt underneath a Prada sweater that’s underneath a Hermès blazer. In my mind, that illustrated guy was canceled about ten years ago and has rebranded multiple times, currently going as an “A.I. guru” who posts daily to LinkedIn. I don’t know exactly when it became a staple, but I think some of its popularity was thanks to the cultural fascination with the bike messenger that I remember picking up in the mid-1990s when Puck from the Real World: San Francisco was the ‘90s version of the “main character,” who people found equally cool and repulsive. It probably didn’t hurt that the urbanite cyclist was becoming a whole nerd culture like craft beer, so getting a bag that you could wear while zooming up and down the avenues was crucial. There were other brands that you’d see in the streets like Timbuk2, but Jack Spade wasn’t really made for bike messengers. It was a designer bag for men. Now that doesn’t seem like such a big deal, but I’d say that Jack Spade doesn’t get enough credit for helping make men feel more comfortable about wearing a bag. It’s embarrassing to even type this, but 20 or 25 years ago if you were a guy and had something hanging from your shoulder, you ran the risk of some jerk with no neck and frosted tips going, “Nice purse.” I’m certain that the bike messenger bag helped change that dumb notion.

A few months after I found one of my old Jack Spade bags, I was reminded of another great bag that you saw around back when #Menswear was a thing after reading an ode to the Filson 258 by one of the only guys who I’ve kept reading since #Menswear was a thing, Michael Williams of A Continuous Lean. The bag in question is discontinued and is beloved by “insiders” because of its look, durability, and the amount of stuff in can hold without looking like a suitcase. I had initially moved on from Spade bags to Filson briefcases well over a decade ago because it’s really the best bag for its money I could find, sturdy as hell, and made in the U.S.A. Now I mostly just drag a big tote from L.L. Bean or Steele around with me because it’s the easiest option for the days when I’m watching the kiddo and also getting a little extra time to myself for work. Diapers, laptop, book, wipes, bottles, notebook, and noise-canceling headphones all fit nicely in a Boat and Tote. I wouldn’t have much use for a Jack Spade messenger bag these days, but I started missing them. They were fun. Andy Spade’s brand distilled into a product; a little preppy, a little everyday guy, with maybe a hint of stolen valor since I’d wager 98 percent of the people who purchased them never worked as a bike messenger, but that’s OK. They could be colorful in traffic cone orange or drab olive or black, and I even liked some of the collabs they did. The Jack Spade x Barbour teaming was one of the only times I’ve been psyched for the British brand to team up with a cool, younger American designer. I liked it so much that I bought one when they came out and I’ve held onto it ever since. Why don’t I use it? I’m not really sure.

They were everywhere, and now you never see them. That’s the thing I can’t get over. I literally never see Jack Spade bags anymore. Part of the reason is because the old nylon ones aren’t easy to find. There’s a nylon backpack, a leather version as well, and there’s a camouflage diaper bag for dads which…I get the appeal now that I’m a father. But the only messenger I could find on the site was a chocolate colored, water resistant waxed one created along with Halley Stevensons mill of Scotland. It’s not available, but even if it was, it’s too sleek for my taste.