Okay so a stranger on the train said something to me last week that I’m still thinking about. I was standing there with my hobo bag basically collapsed against my hip like a sad little croissant, and this woman goes, “that bag looks like it’s already given up,” and got off at the next stop before I could even respond, which, rude, but also. Correct. That is the entire emotional experience of owning a hobo bag. It looks amazing for eleven seconds when you first sling it on and then it just melts into whatever shape gravity wants that day.
I own five of these.
FIVE. I counted them while writing this, standing in my closet at eleven at night having a small crisis about it, and every single one was bought because I convinced myself the last one wasn’t slouchy in the right way. There’s a wrong slouch, apparently, according to me, a person who did not know that was a category until I started buying hobo bags.
Here’s where it gets messy. My sister thinks the soft unstructured leather ones are the only correct version, the kind that basically has no spine and just drapes over your shoulder like it’s tired too. I am team slightly structured, the ones with a tiny bit of shape at the bottom so it doesn’t collapse into itself the second you put a water bottle in it. We have never agreed on this and we are not going to start now, she sent me a photo of hers looking perfectly slouched on a hanger and I sent back one skull emoji, no words, because honestly what else is there to say.
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The inside pockets are a whole separate argument I’m having with myself.
In theory they organize your stuff. In practice I put my phone in the little zip pocket exactly once, forgot it existed, and spent four minutes patting down the outside of the bag like I was getting frisked at an airport. So do the pockets help or do they just give you a more elegant way to lose things. I genuinely don’t know. I think it’s the second one and I think I’m okay with that.
The one I’d actually tell you to try is a gamble, I’m not going to pretend otherwise, it’s the giant slouchy one that looks incredible on camera, filmed beautifully, got compliments in three different group chats, and in person it eats my keys whole and I have to dig for them every single time like I’m searching a couch. If you’re someone who films your outfits more than you live in them, it’s perfect. If you actually need your keys on the first try, maybe not your bag.
