The stereotypical messenger bag is the most unsexy of unsexy carryalls. It looks cumbersome, perpetually laden down with lead pencils, stacks of notebooks, and a big ole half-empty water bottle. Hardly exciting. You’d never wear it on a night out unless you’re going straight from the library to drinks. Even at that point, you’d run home to switch it out.

And yet, despite these decidedly unglamorous associations, the messenger bag feels like a tabula rasa for the return to the office. If you’re hauling things like your laptop to the office, it’s your best bet for a dependable bag that leaves your hands free to hold onto the subway pole or write an email on your phone.

The best versions of the messenger bag, elevated by luxe fabrics like leather and suede, have a groovy ’60s vibe, all casual and easy. The piece had a resurgence in the early 2000s, as noted in the January 2002 issue of Vogue by writer Jenny Comita. She describes them as the bag of choice of your coolest babysitter. “And she found canvas school bags to be completely unoriginal. Instead, she slipped her shoulder through the strap of a big, slouchy carryall inevitably overflowing with gum wrappers, clove cigarettes (don’t tell your mother), and tubes of strawberry lip balm,” Comita writes. The fictional devil-may-care, satchel-toting babysitter eventually went on to graduate from Stanford Business School. Breezy!

On the runways, it appeared in the Michael Kors–era Celine fall 2002 show, worn by model Audrey Marnay along with a super-polished military-style black coat, and also by Maggie Rizer, who simply wore the leather bag with a simple dark green collared (probably cashmere!) sweater. In the spring 2015 Chanel show, which referenced the civil unrest in France in May 1968, the bag made another cameo. Then creative director Karl Lagerfeld whipped up Army green messenger bags scrawled with graffiti and distressed tweed, leaning into the hippie-dippie vibes.

The messenger bag is slowly reappearing in the 2020s too. For the fall 2021 Chloé show, Gabriela Hearst showed fringe-tastic and woven messenger bags, worn with ponchos and knit long-sleeve dresses in the colors of a Southwestern desert sunset. That same season, Balenciaga released a black nylon messenger bag, the kind you’d see sitting next to a gamer, now with the house’s logo stamped on the flap. The internet is chock-full with sturdy Louis Vuitton monogrammed messenger bags, as well as pared-back black nylon Prada iterations. The options are endless as we reenter the world. Plus, being hands-free is always a good look.