My Years-Long Breakup With the Baggu Medium Crescent
And the $33 vintage leather alternative that checks all the boxes
We accept the bag we think we deserve.
To get one thing out of the way, this is not Baggu hateration. I’ve been a longtime wearer of the Baggu medium crescent and an even longer-time user of their reusable totes (I have one in my purse at nearly all times). But in the last few years, I’ve grown increasingly at odds with my crescent.
It had become a purse crutch!
In retrospect, I shouldn’t have bought it in the first place — it wasn’t meant to be, and I’d been ignoring the red flags for years. I’m almost always opposed to logos or brand names on my body (should go without saying that you’re totally allowed to disagree for your own closet), and thus the branded “BAGGU” strap grated on my conscience every time I slung it over my head. Yet I kept reaching for it, like late-night texting an ex who lives in your neighborhood, because fuck it’s convenient!
The water-resistant nylon skin is a good choice for drizzly days and so difficult to stain (it rains more than 100 days a year in NYC, and this was the common denominator of when I reached for it most). It slips right over your tired shoulder, balancing weight across the torso and hips like a circus act. And its capacity is magical: able to hold a Hydroflask and two library hardbacks with ease.
I’ve affectionately referred to the medium crescent as the fuel-efficient mid-sized SUV of purses, and living in the city, a roomy purse is the closest thing you have to the freeing mobile storage of a car. A handheld RAV4 is too tempting to pass up when you’re running out the door ten minutes late for a doctor’s appointment and there’s threat of rain looming in the sky.
But I was always uncomfortable wearing something that wasn’t 100% my style (a lesson I hadn’t quite yet learned in my early 20s when I first got one: don’t waste time and money buying the thing that’s almost perfect, it’s worth it to wait for the perfect thing). And as someone who devotes so much time to pondering fashion — this was unacceptable! And frankly a bit embarrassing! Shouldn’t I know myself better than that?
So I began a search for something to replace it. Like… 5 years ago. A durable and spacious beater bag, more elevated than logo’d nylon but well suited to errands and grocery stores too.
My everyday, any-occasion bag criteria:
Black
Leather
Vintage or secondhand
Rain proof-ish (no suede and had to close properly with a well protected interior)
Holds my 13” laptop
Fits at least two books
Thick strap so it doesn’t cut into my shoulders
The strap had to also be leather and adjustable (I needed sleek from tip to toe and this turned out to be so tough to find)
Have a crossbody-length option for hands-free city schlepping
Inexpensive enough to not feel too precious about
So many purses were almost right. I got really close with a few late aughts Marc Jacobs numbers and one fantastic vintage Bottega that tragically wouldn’t have fit my laptop. I was incredibly strict with myself, refusing to acquiesce to a bag that wasn’t perfect, fully committed to never settling.
I scoured TRR for higher end options; I macheted my way through the eBay jungle where the search term “vintage leather crossbody” yields more than 130,000 results; and I sighed with desperation perusing Poshmark, Depop, and occasionally Japanese eBay, hoping to stumble upon a miracle. I swiped left on thousands of bags. My eyes were bleary from out-of-focus photos and listing typos, and I was beginning to worry my perfect purse would die in rose jail.
So I came up with a temporary solution: “upgrade” the Baggu.
Crescent 2.0 — When the Collina Strada collab came out in spring of 2024, I snagged the plain black crescent. My reasoning: the strap was a higher quality, silkier material, and the big silver buckle made the bag feel more like me. It was a nice design touch, and I liked that bag a little bit more than the one before. I hated myself less when I wore it.
Crescent 3.0 — When the Molly Goddard collab came out in the summer of 2025, I promptly sold my Collina Strada one and replaced it with the button-strapped black crescent. SANS LOGO! I could maintain my go-to rain bag without feeling assaulted by the branding across my chest, I reasoned.
I don’t hate this version at all. I actually love this shiny industrial button-strapped design, it just still didn’t meet my criteria. Even without the logo, it was too casual, didn’t fit a laptop, and wasn’t leather. I was annoyed with myself for trying so hard to make it work when it, at this point, it hadn’t been working for years. We were long past couples therapy by now.
All the while, as I willed my crescent to change (they never change), I was searching high and low on resale sights for something to curb my insatiable appetite. It seemed like a hopeless feat.
Until I found it — in 2026, six years after my first Baggu purchase.
A black leather, silver-buckled messenger bag originally released in the fall of 2004. I submitted an offer on Depop for $33 — a risky move allowing time for someone to swoop in and buy it out from under me, but I respect the game too much not to send a lower offer. Thank GOD she accepted.
I’ve worn it nearly every day since it arrived: to work functions, to the farmer’s market, to an ultramarathon my partner ran in the Pennsylvanian mountains. It clings to my hip tautly, swaddles my laptop gently, and has already survived a couple spring drizzles.
It’s vintage Banana Republic, and I knew the leather would be scrumptious because I have my mom’s buttery smooth BR leather jacket from the ‘90s hanging in my closet. The specs:
Thick, heavenly leather
Vintage and only $33, major win
Fits my laptop
Can hold 4-5 books if that ever becomes necessary (or one really girthy epic)
Varying strap length options, from low-slinging to tight on the hip where I prefer
Internal and external mini pockets for extra organizational promise (a mysterious small one in the upper middle behind the big flap too, I texted Liana Satenstein to see if it might be an old Palm Pilot/flip phone pocket — she confirmed yes!)
Silver hardware with buckles and rivets for some design intrigue
Perfect intermediary size: big enough to schlep, not too big to be confined to casual settings
With the messenger bag’s historical origins in mail carry, it’s only fitting for it to hold the digital mail I send to you every week. Back to her roots she goes! Now I just need to see about getting a horse.
Some secondhand bags I found for you:
Vintage Sonia Rykiel black leather messenger, $85 (fair condition but so cool)
Giorgio Armani black leather messenger, $105 (the bow detail!?)
And I can’t not share the Kate Spade messengers, which aren’t leather but have been on my watchlist for so long (they might actually be diaper bags? one comes with a fold-up changing mat!):
Kate Spade pink corduroy messenger, $72 (I actually shared this a while back and I can’t believe it hasn’t sold, I’m obsessed with it)
So what’s happening to the Baggu 3.0 now? I’d love to tell you this break-up is final. I’d love to tell you I kicked her out of my house already, burned her clothes on the lawn and blocked her Instagram. But that would be a lie… Part of me is still hoping she’ll change! Or that maybe someday I’ll change and see her in a new light.
For now, she’s been relegated to the back of my closet, and with a little more distance from the heat of the situation, I’ll reevaluate her place in my life and in my wardrobe. If anything I hope my messy breakup can serve as a reminder to trust your sartorial instincts. Don’t force it. You deserve better.
Get in touch with me at mackinley@yeehawt.com if you’d like to work together, browse my shelves here, or follow me for more vintage and fashion chatter on IG and TT.
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Warm weather incoming…
