When Gracie Wiener ordered a canvas Boat and Tote bag through the L.L. Bean website in July 2021, she filled out the “add monogram” field with the word “psycho” instead of her initials. “I think it’s funny to wear your best, or worst, qualities on your sleeve,” she said.
Ms. Wiener, 26, who lives in Manhattan and is the social media manager for Air Mail, was inspired by a picture of a similar bag that Juliana Salazar, a stylist, had posted on Instagram. In February Ms. Wiener created an Instagram account, @ironicboatandtote, to circulate pictures of the bags among her friends, who ordered “EGOMANIAC” and “emotional baggage” totes of their own.
Ms. Wiener’s Instagram account, which has 26,000 followers, documents the young millennials and members of Gen Z who are stitching a contemporary sense of humor onto an enduring symbol of American prep.
Within L.L. Bean’s 10-character maximum, there are cheeky directives (“scam him,” “bite me”) and self-deprecation (“moody,” “narcissist”), as well as nods to astrology (“august leo”) and Taco Bell (“LIVE MAS”).
The trend may have translated to increased sales of the Boat and Tote, especially among younger customers, Amanda Hannah, an L.L. Bean spokeswoman, wrote in an email. “Boat and Tote sales are up 30 percent over last year and have been one of the top drivers of new buyers this spring and summer,” she said. “It’s been really fun seeing a new generation of customers taking our classic tote and making it their own.”
Sarah Thompson, a 26-year-old social media manager in Boston, crowdsourced ideas on Instagram before ordering a Boat and Tote that says “dump him” in pink cursive.
“My mom doesn’t get it, which I think is funny,” said Ms. Thompson, whose mother owns one of the bags monogrammed with her initials. “She’s like, ‘What do you mean, dump him? You don’t have a him to dump.’”
Introduced in 1944 as an ice carrier, the Boat and Tote is as much a staple of preppy fashion as polo shirts, chinos or penny loafers, said Chris Black, a host of the podcast “How Long Gone.” He said the bag’s customizability and relatively low price — $30 to $55, plus $8 for the monogram — make it a democratic entry point into the preppy aesthetic, which is mounting a comeback.
Novin Abdi, 23, made her first L.L. Bean purchase in July: a “thanks, i hate it” Boat and Tote.
Ms. Abdi, who is Iranian and grew up in Texas, used to think of L.L. Bean as “the traditionally white, straight, WASP-y” brand that was only targeted toward people on the East Coast. Adding one of her favorite phrases made the bag feel more like her own.
“The more we complicate what ‘preppy’ looks like or what ‘classic’ style looks like, the better,” said Jesica Wagstaff, 40, a style content creator in Virginia whose TikTok video featuring her monogrammed Boat and Tote has been viewed more than 550,000 times.
“It’s a little badge of your personality,” said Austin Riggle, 28, who works in marketing in Cleveland, and whose boss was amused when Mx. Riggle showed up to work with an extra-large Boat and Tote that said: “GAY PANIC.”
Others have used their canvas totes to poke fun at luxury handbags.
Garrett Gottesman, 29, ordered a “Balenciaga” Boat and Tote in June. L.L. Bean would not embroider the bag with a trademarked brand name, so Mr. Gottesman, who works in social media in New York City, brought the blank bag to an embroidery shop in the garment district that carried out his vision for $30. “Well worth it,” he said. (L.L. Bean will also not embroider any profanity on its totes, though some abbreviations have sneaked through.)
Not everyone is sold on the trend’s sustainability. Sara Morano, 30, an executive assistant who lives in Greenwich, Conn., said she worries that adding an of-the-moment phrase like “flop era” to a durable bag might make people discard it more quickly.
But there are ways to participate without buying any new bags, said Ysabel Morales, a 22-year-old student at Otis College of Art and Design in Los Angeles. She bought a Boat and Tote secondhand that says “not my circus,” and on July 13 she got a tattoo of a “psycho” tote on her right arm.
Ms. Morales said the bag was an obvious addition to her collection of body art, which includes line drawings of a LaCroix seltzer can and a Marcel Breuer Wassily Chair. “I just thought it was iconic.”