What to Wear on a Boat: The Coastal Grandma Aesthetic

My favorite lake days explain why I love the coastal grandma aesthetic. They also explain why I named my brand Sunday Drive—even though the best part of those days usually happens on the water.

Growing up near Lake Erie, I learned that a boat ride rarely ends when you get back to the dock. Someone suggests dinner in town. Dinner turns into an ice cream run. Then the sky starts changing, and suddenly nobody wants to head home.

Those are the days I want to get dressed for. I want to feel comfortable and put together, with enough room in the plan to stay out a little longer.

To me, coastal style captures that feeling: familiar, relaxed, and never too precious to actually enjoy yourself. But what makes an outfit work for the whole day, from the first boat ride to the last stop?

It starts with looking at the clothes you already reach for and giving a few of them another way to be worn.

Make the Coastal Grandma Aesthetic Your Own

The name might suggest a very specific look, but you don’t need a vacation house or an entirely new wardrobe to make it yours. What draws me to this style is the feeling of being at ease. Nothing needs constant adjusting, and you can sit down, eat lunch, or catch a breeze without worrying about your outfit.

Before packing for a boat day, I’d start with what you already own. Which shirt feels better after every wash? Which shorts can you comfortably spend hours in? Which sweatshirt somehow makes it into every overnight bag?

Those pieces are worth building around.

For me, the coastal grandma aesthetic works best when it feels personal. If you love stripes, wear them. If your favorite lake sweatshirt has been around for years, bring it. An outfit becomes more interesting when it reflects your actual life.

I’d also consider what the day involves before choosing anything. An afternoon spent swimming calls for something different than an evening cruise followed by dinner. Knowing the loose plan helps you pack clothes you’ll use without bringing half your closet.

Start With Pieces That Can Do More Than One Job

For a warm afternoon on the water, I’d build my outfit around a swimsuit and a loose button-down. Blue-and-white stripes would probably be my first choice. They remind me of summers by the lake, and they’re easy to wear with the basics I already own.

Wear the shirt open over your swimsuit while you’re on board, then button it when you stop for lunch. If you head into town afterward, you already have the beginning of an outfit.

You don’t need to buy a shirt specifically labeled as a cover-up, either. Try the oversized button-down sitting in your closet before adding another one to your cart.

The same idea applies to bottoms. I’d choose cotton drawstring shorts or relaxed linen pants that let me sit comfortably and move around easily. Think about stepping onto the boat, sitting on a seat, and reaching into your bag. If something feels restrictive while you’re getting ready, it probably won’t feel better a few hours later.

A simple tee is another piece I’d make room for. You can pull it on after swimming, wear it with shorts, or tuck it into pants for dinner. That’s how I picture a Sunday Drive tee being worn: as part of a day you’re already excited about.

Try laying out two possible outfits using the same shirt before you leave. If changing the bottoms is enough to take you from the boat to dinner, you’ve saved yourself some packing.

Bring the Layer You’ll Be Glad You Packed

The outfit I picture most clearly on a Lake Erie evening is a sweatshirt pulled over a swimsuit, with shorts and slightly messy hair. By that point, everyone has spent enough time outside that getting comfortable feels especially good.

Even when it’s warm as you leave, think about the ride home. I’d bring a layer that fits comfortably over my shirt and is easy to pull on without rearranging my entire outfit.

This is where a Sunday Drive mockneck fits into my own lake-day wardrobe. I picture reaching for it when the breeze picks up and keeping it on while we decide whether there’s time for one more stop.

A sweater or crewneck you already love can serve that purpose, too. Choose something you’ll be happy wearing for the rest of the evening.

That’s part of the appeal of the coastal grandma aesthetic for me: the comfortable layer belongs in the outfit. You don’t have to sacrifice the feeling of being put together when you get cold.

Before leaving, try your layer over what you plan to wear. Check that the sleeves feel comfortable and that you can move easily. It’s a small step, but it’s better than discovering that your favorite sweater doesn’t fit over your shirt once you’re out on the water.

Keep the Details Easy, From the Boat to Dinner

Shoes and accessories should make the day easier. Ask the boat owner what footwear they prefer, then choose something suitable for moving around on board.

For accessories, I’d bring sunglasses, a secure hat, and a small bag for the things I want close by. A hat you don’t have to chase is especially valuable (speaking from experience).

I’d leave delicate or sentimental jewelry at home if I knew I’d spend the day worrying about it. Being able to relax matters more to me than adding one more accessory.

If dinner is part of the plan, think about a small change you can make after docking. I’d swap my swim shorts for linen pants and tuck in my tee. For an evening boat ride, I might wear that combination from the start and keep my mockneck nearby.

Try this before your next lake day: choose one shirt, two bottoms, and one layer from your closet. Put together an afternoon outfit and an evening outfit using those pieces. Take a quick photo of each so you have an idea ready the next time you’re packing.

You may find that the outfit you were looking for was already there.

The Coastal Grandma Aesthetic, the Sunday Drive Way

Sunday Drive comes from those days I never want to rush: time on the water with family and friends, a good sandwich packed for lunch, and a stop for ice cream before watching the sunset. The drive home becomes one more part of the day worth enjoying.

That’s what I want our tee and mockneck to become part of. The tee you wear again because it works with your favorite shorts. The mockneck you keep nearby because you know you’ll want it later. Pieces that earn their space through the memories you make wearing them.

Before buying something new, try a different combination of what you own. If there’s a gap, choose something you can picture wearing well beyond one afternoon.

For me, the coastal grandma aesthetic comes down to feeling comfortable enough to say yes when someone suggests staying a little longer. Get dressed for that possibility. The sunset might be the best part.

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Looking for a little inspiration? I’ve linked a few of my favorite pieces for the coastal grandma aesthetic below, alongside the Sunday Drive styles I’d bring along.

An oversized button-down: An easy swimsuit cover-up that works just as well tucked into shorts for lunch.

Relaxed linen pants: For heading into town after a day on the water.

A classic cotton sweater: A familiar layer for breezy evenings.

The Sunday Drive tee: Wear it over your swimsuit, then tuck it into your favorite pants for dinner.

The Sunday Drive mockneck: The layer I’d pack for the ride home—and reach for again during the week.

Use these as inspiration, starting with what’s already in your closet. My favorite part of the coastal grandma aesthetic is finding pieces you’ll keep living in, long after the boat is back at the dock.

What to Pack for a Lake Weekend: Leave Room for the Good Stuff

When I think about what to pack for a lake weekend, I picture the moment the bag is finally in the car. The windows are down, someone has control of the music, and the only thing left to decide is where to stop for lunch.

Getting to that point is usually where I complicate things.

Suddenly, I’m packing for three different versions of the same weekend. There’s the sunny one, the rainy one, and the one where I apparently change outfits four times a day. By Sunday, half the bag hasn’t been touched, and I’ve worn the same sweatshirt both nights.

Growing up near Lake Erie has taught me a few things about packing. Mostly, that my favorite weekends involve a loose plan and a small rotation of clothes I feel good in.

The trick is figuring out what deserves space in your bag. Here’s where I’d start.

What to Pack for a Lake Weekend Starts With the Plan

Before pulling clothes out of your closet, find out what the weekend actually involves. Are you staying at someone’s house or a rental? Will you spend most of the day on a boat? Is there a dinner reservation, or is the evening plan more likely to involve takeout on the porch?

You don’t need an itinerary for every hour. A few details will help you avoid bringing things you won’t use.

Check the forecast close to departure, including the evening temperatures. Then ask your host what’s already available. Towels, bedding, and kitchen supplies take up space quickly, so it helps to know what you’re expected to bring.

I’d also confirm anything needed for planned activities. If you’re joining someone on their boat, ask what they want you to bring and what they already provide. Your weekend tote is only one part of getting ready.

My starting list would look something like this:

• Two swimsuits, so one can dry while I wear the other.

• Two or three everyday tops.

• One pair of shorts and one pair of relaxed pants.

• A comfortable sweatshirt or mockneck.

• Pajamas, underwear, and any other daily basics.

• Shoes suited to the plans.

• A light rain layer if the forecast calls for it.

Adjust the quantities to your trip. The point is to give yourself enough options without packing a separate wardrobe for every possible mood.

Pack Outfits That Share Pieces

The easiest way to overpack is to choose each outfit separately. A top for Saturday afternoon somehow becomes a top, specific bottoms, different shoes, and another bag. Repeat that a few times, and you’re bringing enough for a week.

Instead, I’d choose clothes that work together.

For a Friday-to-Sunday trip, I’d start with a tee I can wear with both shorts and pants. Add an oversized button-down that works over a swimsuit or buttoned up for lunch. Then bring a layer that fits comfortably over either.

A Sunday Drive tee and mockneck are the pieces I picture here. The tee can come along for the daytime plans, and the mockneck is what I’d reach for once the evening cools down. Both should still make sense in your wardrobe when the weekend is over.

For dinner, I’d change into relaxed pants, tuck in my tee, and keep the rest simple. If there’s a specific occasion that calls for something dressier, pack for it. Otherwise, think about whether the clothes you’re already bringing can do the job.

When deciding what to pack for a lake weekend, try everything together before it goes into the bag. You might discover that two tops cover most of your plans, or that the extra pair of shoes doesn’t add much.

Comfort matters here, too. Bring the shorts you can sit in for hours and the shirt you don’t constantly adjust. A weekend away is a good time to wear your favorites.

The Boat Tote Has Earned Its Spot

I should probably admit that the L.L.Bean Boat and Tote has become my whole personality. At this point, choosing what goes inside it is only part of the preparation. Deciding which color combination best represents me as a person is apparently the other part.

But a roomy tote does have a useful role in a lake weekend. It gives you one place for the things that move with you throughout the day.

I’d use my overnight bag for clothes and keep the tote ready for the boat, beach, or afternoon out. That way, I’m not digging through pajamas to find my sunglasses while everyone else is waiting to leave.

Inside, I’d keep:

• Sunscreen and lip balm with SPF.

• Sunglasses and a secure hat.

• A refillable water bottle.

• A towel, if needed.

• A book or something to do during a quiet afternoon.

• A small pouch for keys, lip balm, and other easy-to-lose items.

I’d also bring a separate bag for a wet swimsuit. It’s a small thing that makes unpacking much more pleasant.

As much as I love a canvas tote, I wouldn’t rely on it to keep my phone or other valuables dry. Use appropriate protective storage for anything that needs it, and think about where the bag will sit during the day.

The goal is to have the essentials easy to find. Whether your bag is monogrammed is between you and your personality.

Remember Lunch, the Ride Home, and the Small Stuff

Clothes tend to get most of my attention when packing, but the small practical things usually make the biggest difference once I arrive.

Start with your daily routine. Bring your medications, toiletries, phone charger, and anything else you rely on at home. A weekend bag doesn’t need an entirely new beauty routine. I’d pack the products I actually use and leave the “maybe I’ll try this” collection behind.

Then think about food. If you’re staying with friends or family, ask what would be helpful to contribute. Breakfast supplies, sandwich ingredients, or a snack everyone likes can be more useful than arriving with a random assortment.

Personally, I want a good sandwich involved somewhere in the weekend. Planning lunch before leaving means I can spend more time enjoying the day once I’m there. If you’re bringing perishable food, make arrangements to keep it properly chilled.

I’d also set aside something comfortable for the trip home. It can be the same outfit you traveled in, provided it’s still clean and ready to wear. Keep it somewhere separate from damp towels and swimwear.

One final check I like is to walk through the first morning in my head: waking up, getting dressed, having breakfast, and leaving for the water. Anything I’d immediately need during that routine should be easy to reach.

Try this before zipping your bag: make three short lists labeled “wear,” “carry,” and “confirm.” Put outfits under wear, daily essentials under carry, and questions for your host under confirm. Check each one off as you go. It’s an easy checklist to save on your phone and reuse for the next trip.

My Lake Weekend Packing Favorites

Once you’ve figured out what to pack for a lake weekend, the best part is being ready when someone says it’s time to go. You know where your sunglasses are, you have something warm for later, and there’s room in the day for a plan you haven’t made yet.

Below are a few of the pieces I’d bring, along with some packing essentials I love. Start with what you already own and use these links for anything you’re missing.

L.L.Bean Boat and Tote: For the day’s essentials and, in my case, an unreasonable amount of emotional attachment.

A small zip pouch or duffle: To give keys, chargers, and little items a place of their own.

A bag for wet swimwear: To keep the damp things separate on the way home.

An insulated cooler: For the lunch you’ll be very happy you packed.

The Sunday Drive tee: An easy piece to wear with shorts during the day and pants afterward.

The Sunday Drive mockneck: For the evening breeze, the ice cream line, and the drive home.

For me, deciding what to pack for a lake weekend comes down to bringing what helps me enjoy being there. A few familiar clothes, the things I’ll need on the water, and a tote by the door. Once those are ready, I can get back to the more pressing question: who’s making the sandwiches?