A Preppy Staple Got an Ironic Makeover This Summer

Jesica Wagstaff, 40, tried to order a new tote this spring to add to her collection of five, four of which are monogrammed, and received a backorder notification for the first time she can remember. In March, she posted a look at her outfit on TikTok—a sweater set and crisp denim with a matching monogrammed Boat & Tote—and it hit over half a million views. “Growing up in a Northern Virginia private school, I think they’re a prerequisite for attendance,” says Wagstaff, who adds she saw her first ‘Gucci’-monogrammed Boat & Tote fifteen years ago. “Here is a bag that communicates a very specific lifestyle and the wearer opted to complicate that message with a simple rebrand.”

Originally created as an ice carrier in the fall of 1944, the tote’s original purpose was function, not form. L.L. Bean founder Leon Leonwood Bean would, for example, use the bag to transport ice to his cabin in the woods of Maine. It was reimagined as the Boat & Tote in 1965 and, over time, became L.L. Bean’s top-selling accessory. To this day, it’s still crafted from the same double layered material used in conveyor belts—meaning it’s durable enough to be passed down from generation to generation.

“The Boat and Tote is a perfect example of the ingenuity of American design,” says Pushor. “The East Coast has historically been where the wealthiest Americans lived, played, and made their fortunes, and there has always been a desire to emulate the clothing of the rich and powerful. If you could not afford your own sailboat, you could at least dress like it.”

The TikTok-friendly monograms can give the bags an appealingly irreverent knock-off feel without knock-off quality. The 2022 product line includes a range of colorways (including faded jade, lawn green, red wine, and regatta blue), sizes, strap lengths, models (open and zip-top), and customized monograms in five different fonts and 48 thread colors. Prices start at $29.95 with a monogram up to 10 characters costing just eight additional dollars. Each one is made in L.L. Bean’s Maine manufacturing center by stitchers who can fabricate a bag in just seven minutes. To keep up with the brisk sales, the L.L. Bean design team is continually expanding its product line, says Hannah. With the 80^th anniversary approaching in 2024, she says to keep an eye out for “more exciting updates.”