When I’m not carrying a basket bag in the summer, my favorite casual bag is the iconic Boat and Tote. There are some pieces that transcend trends and seasons — and the Boat and Tote is one of them. This humble, heavy-duty canvas bag has quietly become a cult classic, spotted everywhere from grocery stores in Maine to farmers markets in Brooklyn, from beach clubs in the Hamptons to Parisian airports. And with a price range of $25-$90 depending on the style, it’s also accessible, but has still become a bit of a preppy status symbol. So what exactly makes the Boat and Tote so timeless — and somehow so chic?
A Brief History of the Boat and Tote
The Boat and Tote dates back to 1944, when L.L. Bean introduced it as the “Bean Ice Carrier.” Yes, ice. Made from durable cotton canvas with double-stitched seams and a reinforced base, the bag was designed to haul 200+ pounds of ice from car to cabin. It was built for function — not fashion.
But over the decades, this utilitarian tote became a staple in households across the U.S., beloved for its strength, simplicity, and New England preppy aesthetic. By the 1960s, L.L. Bean rebranded it as the “Boat and Tote,” and it began showing up at sailing clubs, summer camps, and East Coast universities.
Today, the bag still uses the same design, materials, and manufacturing process — each one is hand-sewn in Maine — and it remains one of the brand’s most beloved products.
Why the Boat and Tote Is So Chic Right Now
You could call it preppy, coastal grandma, or quiet luxury — whatever the term, the Boat and Tote fits into the fashion zeitgeist effortlessly. Here’s why:
- It’s understated: The Boat and Tote feels refreshingly unfussy. Its crisp shape and clean lines make it feel elevated, even minimalist.
- It’s timeless: The design hasn’t changed in 80 years, and that’s exactly the point.
- It’s functional: You don’t have to baby this bag. Throw in sunscreen, books, your laptop, a baguette, or all of the above. The canvas wears beautifully and lasts for decades.
- It’s a blank canvas — literally: The Boat and Tote’s minimalist silhouette makes it a perfect canvas for personal style.
Creative Ways to Customize Your Boat and Tote
One of the most charming things about the Boat and Tote is how personal it can become. L.L. Bean’s monogramming options have led to some legendary custom bags.
Here are some standout ways to make it your own:
1. Classic Monograms
Stick with a traditional monogram — your initials, family name, or even a cottage name (“Hill House,” “The Cape,” “Grove House”). Choose navy or red for a timeless look.
2. Ironic Labels
This is where the fun begins. Social media made ironic monograms a viral trend — think:
- “DRAMA”
- “BAG LADY”
- “LOW MAINTENANCE”
- “VIBES”
The juxtaposition of cheeky phrases on a preppy bag is fashion gold.
3. Color Play
The Boat and Tote comes in a range of base and handle color combinations — classic navy, bright pink, forest green, black, and more. Mix and match to reflect your mood or season:
- Neutrals for year-round wear
- Pastels for spring
- Bold primaries for summer
4. Sizes for Every Style
The Boat and Tote comes in four sizes: small, medium, large, and extra-large. Each lends itself to different uses:
- Small: A chic alternative to a handbag
- Medium: Perfect everyday carryall
- Large: Ideal for beach days, road trips, or errands
- Extra-Large: Weekends away or hauling everything under the sun
It can be customized with short or long handles depending on your preference.
How to Style It
The Boat and Tote is incredibly versatile. Here’s how to make it feel intentional — not just practical:
- With a white button-down, denim shorts, and sandals for the ultimate “coastal cool” vibe
- Tucked into the crook of your arm with a summer dress — instant “editor off-duty” energy
- With tailored trousers and a tank for a clean, modern balance
- With a swimsuit, oversized sunglasses, and a silk scarf — très French Riviera
Whether you’re heading to the farmers market, your favorite pilates class, or a summer weekend getaway, the Boat and Tote adds just the right amount of laid-back polish.
The Lands’ End Canvas Tote: A Chic Contender
While L.L. Bean may have created the original Boat and Tote, Lands’ End has quietly built a loyal following for its own version — and it’s worth paying attention to if you’re looking for more customization, extra features, or a slightly different aesthetic.
Here’s what makes the Lands’ End Canvas Tote stand out:
Lighter Yet Durable
Lands’ End’s tote is made from a slightly lighter canvas (24 oz. for the open top, 20 oz. for the zip top), but it’s still rugged, structured, and reinforced with a flat, squared-off base. It holds up well to everyday use and softens over time for a lived-in look.
Interior Features
- Interior pockets
- Key fob loops
- Water-resistant finishes (on some styles)
More Customization
Lands’ End offers canvas totes with fun prints like stripes or hearts, offering more design flexibility. They also offer embroidered monograms and icons — from initials to flowers, boats, and even paw prints for pet lovers.
Affordable and Often on Sale
Another reason the Lands’ End tote is so popular? Frequent discounts. While both totes are similarly priced at full retail, Lands’ End regularly runs sitewide sales and promo codes, which can make theirs a more budget-friendly option — especially if you’re customizing multiples.
L.L. Bean vs. Lands’ End: Which Tote Is Right for You?
| Feature | L.L. Bean | Lands’ End |
| Canvas Weight | 24 oz. | 20-24 oz. |
| Made In | Maine, USA | Imported |
| Top Closure | Open or zip | Open or zip |
| Customization | Classic monogramming | Monogram + icons + color blocking |
| Interior Features | Minimal | Pockets, zipper, key fob (select styles) |
| Price | Full-price more consistent | Often discounted |
Ultimately, if you’re a purist who values heritage and American craftsmanship, the L.L. Bean Boat and Tote is hard to beat. But if you’re looking for more color options and built-in functionality, the Lands’ End tote may actually suit your lifestyle better.
And honestly? You can’t go wrong with either — they’re both chic, functional, and perfect for everything from beach weekends to farmer’s market hauls.
Both brands are also branching out into cute bag charms/keychains like the L.L. Bean Micro Tote Bag and the Lands End Mini Canvas Tote.
In a fashion landscape where trends can come and go quickly, the Boat and Tote remains steady. It’s stylish without trying too hard, practical, and endlessly personalizable. Whether you’re a minimalist or a maximalist, a prepster or a creative, there’s a Boat and Tote for you.
Do you have a Boat and Tote you love? Share your monogram ideas in the comments — or tell us your dream combo!
Xo,
Courtney
The Real Chic Life 
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