The Sea Bags Collection I’ve Built One Trip at a Time

One trip to Maine. One Christmas gift. One collection that has followed me through more than a decade of life.

There are some purchases you plan for, and then there are the ones that quietly become part of your story.

For me, that story started in 2015.

That year, I took what I still think of as my “self vacation” to Maine. I wandered through coastal towns, explored the waterfront, and eventually found myself inside a Sea Bags store. I immediately fell in love with the concept—beautiful bags handcrafted in Maine from recycled sailcloth that had already lived a life on the water.

There was just one problem.

At the time, they were out of my budget.

So I admired them, imagined bringing one home, and reluctantly walked away.

That Christmas, my mom surprised me with the tan Chebeague Tote I’d fallen in love with.

Neither of us knew it then, but she wasn’t just giving me a bag.

She was starting a collection.

Looking back now, I sometimes wonder if my 2015 self knew something my future self didn’t. Because today I live in a small coastal town where these bags have become part of my everyday life. Whether I’m heading to the farmers market, spending the day on the boat, shopping along the waterfront, or packing for a weekend away, there’s almost always a Sea Bag coming with me.

More than ten years later, they’re still some of the most-used bags I own.

Why Sea Bags Have Earned a Permanent Place in My Collection

One of the things I appreciate most about Sea Bags is that they embody the philosophy behind Looks More Expensive: buy thoughtfully, buy well, and use what you own.

Every Sea Bag begins as a retired sail that has already spent years on the water. Rather than ending its life in a landfill, that sail is transformed into something new by skilled craftspeople in Portland, Maine. Every bag is handcrafted in the United States, making each one a little different from the next.

I also love supporting companies that stay connected to the communities that inspired them. Sea Bags’ commitment to American craftsmanship and their support of an all-women’s sailing team are details that made me appreciate the brand even more over the years.

Most importantly, these bags have proven themselves.

They’re durable enough for real life, timeless enough that they never feel dated, and they somehow look just as appropriate today as they did when I received my very first one more than a decade ago.

The Bags That Earned Their Place

Every bag in this collection has a purpose. None were purchased just to sit on a shelf, and every one has become part of a different chapter of my life.

Tan Chebeague Tote

Everything started here.

My mom gave me this tan Chebeague Tote for Christmas after my solo trip to Maine in 2015. More than ten years later, it’s still one of the bags I reach for most often. The classic shape works with everything from jeans and sneakers to a sundress, and it’s still the one I’d recommend to anyone buying their very first Sea Bag.

Jolly Roger Tote

Living in a coastal town means there are always fun events on the calendar, and this tote has become part of one of my favorites.

Every August, my little town hosts its annual Pirate Invasion, and I look forward to pulling out my Jolly Roger tote for the festivities. It’s the perfect bag for a town that fully embraces its pirate history, and it’s become part of one of my favorite local traditions.

Most often used for: Pirate Invasion, waterfront festivals, and coastal events.

Pink Lobster Tote

This one wasn’t planned—it was pure impulse.

A friend was visiting, and what started as an afternoon of shopping along the waterfront somehow turned into drinks… which somehow turned into more shopping. That’s when I spotted the pink lobster tote. I bought it on a whim, and I’ve never regretted it. Today it’s my unofficial golf cart bag. It matches my pink golf cart perfectly and has become my favorite for farmers market mornings, waterfront shopping, and running errands around town.

Most often used for: Farmers markets, waterfront shopping, and golf cart errands.

Navy Mariner Stripe Chebeague Handbag

If you’ve spent much time on Looks More Expensive, you’ve probably seen this tote before.

It’s my go-to for boat days, Big Rock, the farmers market, beach days, and just about anything else that involves being outside near the water. It’s roomy without feeling oversized, lightweight, and perfectly at home in my coastal lifestyle.

Most often used for: Boat days, beach days, farmers markets, and waterfront events.

Navy Mariner Stripe Chebeague Crossbody

This bag has probably evolved more than any other in my collection.

I actually removed the crossbody strap and permanently turned it into my sunscreen bag. It stays packed with my everyday SPF essentials, so I simply drop it into whichever tote I’m carrying that day. It’s one of those little systems that has made life easier, especially during the summer.

Most often used for: Organizing my sunscreen and beach essentials.

Vintage Essential Weekender

Whenever I want things to feel a little more contained, this is the bag I grab.

The zippered top keeps everything secure, the shoulder strap makes it comfortable to carry, and it’s the perfect size for weekend trips or quick getaways. When I don’t need rolling luggage but still want to stay organized, this is my favorite travel companion. And I usually pair it with the Preppy Stripe Pier Tote loaded up with my bathroom essentials - hairdryer, flat iron, and makeup bag.

Most often used for: Weekend trips and overnight travel.

Preppy Stripe Pier Tote

I use this tote when I’m traveling back and forth to my mom’s. It’s roomy without feeling oversized, lightweight, and can fit a whole lot of clothes. For my items that I want to keep more contained, I pair it with the Vintage Essential Weekender, so it makes a nice, coordinated-looking set.

Most often used for: wrangling travel chaos.

Red, White & Blue Buoys Tote & Beverage Bucket

These only make appearances a few times each year, but they’re part of some of my favorite traditions.

Every Memorial Day and Fourth of July, they’re guaranteed to come out. The tote is perfect for patriotic weekends on the coast, while the beverage bucket is one of the smartest entertaining pieces I own. It holds six drinks around the outside while ice fills the center, creating a collapsible cooler that’s perfect for backyard gatherings, boat days, or fireworks. When it’s not keeping drinks cold, it even works as a surprisingly handy organizer around the house.

Unfortunately, Sea Bags no longer makes this particular buoy pattern. If you fall in love with it the way I did, I’d highly recommend keeping an eye on Poshmark or other resale sites—you never know when one might become available.

Most often used for: Memorial Day, Fourth of July, and summer entertaining.

If You’re Buying Your First Sea Bag

If I were starting my collection all over again, I’d buy the Chebeague Tote without hesitation.

It was my very first Sea Bag, and after owning it for more than a decade, I still think it’s the most versatile style they make. The classic silhouette can be dressed up or down, and it comes in timeless colors that won’t go out of style. It’s one of those rare bags that feels just as appropriate carrying into the office as it does heading to the farmers market or spending the weekend by the water.

I also think it’s one of the best examples of what makes Sea Bags special. The recycled sailcloth is paired with rugged waxed canvas that helps repel light moisture and stands up beautifully to everyday wear. Add premium leather handles, antique brass hardware, and a zipper closure, and you have a bag that’s built for years of real life—not just one season.

Knowing what I know today, it’s still the bag I’d buy first.

More Than a Collection

When I walked into that Sea Bags store in Maine back in 2015, I never imagined I’d still be adding to this collection more than ten years later.

I certainly never imagined I’d someday live in a coastal town where these bags would become part of my everyday routine.

Looking back now, it feels like that first Christmas gift from my mom wasn’t simply the beginning of a collection.

It was the beginning of a story.

Today, every bag reminds me of a different memory—a solo trip to Maine, afternoons with friends, weekends on the water, holidays by the coast, and everyday moments that have become part of the life I’ve built.

That’s why I continue reaching for Sea Bags year after year.

Not because I collect bags.

Because I collect the memories that come with them. -LME

A Note About This Partnership

Sea Bags is one of the first brands I’ve partnered with directly through an affiliate program, and that partnership means even more because this collection existed long before the affiliate relationship did.

I purchased these bags over the course of more than a decade (with the exception of the very first one, which was a Christmas gift from my mom in 2015). No one asked me to write this article, and all opinions are entirely my own.

Thank you for supporting Looks More Expensive by shopping through my affiliate links. Every purchase helps me continue creating thoughtful, real-life content like this.