These Memorial Day Outfits Feel Like a Soft Launch for Summer

Memorial Day weekend is the unofficial start of summer. At least in my book. Every year my family and I pack up the car and head to our summer house in upstate New York. The drive is long but kind of romantic—a matcha latte, a really good playlist, and the smell of trees actually doing their thing again after winter. I like to treat my Memorial Day outfits as a soft launch for summer style—a chance to test out new trends and see what works.

This post is all about memorial day outfits.

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Once we’re there, it’s a whole reset. We open all the windows, do a big family grocery run, and eat dinner on the porch even if it’s still a little chilly. I usually live in comfy layers for the drive, switch into something cute for cocktails the next day, and rotate between cottagecore looks and boat outfits for the rest of the weekend. It’s laidback and a little chaotic in the best way.

Here’s what I’m packing this year—trust me, you’re gonna want to copy everything.

Memorial Day Outfits

Day One – Friday | Drive Upstate + Grocery Run

The Plan: We’re packing up and heading to our summer house in upstate New York. The drive is long but honestly one of my favorite parts—windows cracked, playlist on point, and that first glimpse of green after winter still feels magical every year. Once we arrive, we do the classic big family grocery run (yes, all of us… in one cart), then eat dinner on the porch even if we’re still wearing sweaters.

The Look: I’m keeping it cozy but presentable. Soft cotton shorts and a classic white tee, layered with an oversized flag sweater. Ribbed crew socks and Birks for the drive, plus a baseball cap to pull it all together. Gold mini hoops and a big tote bag packed with road trip snacks—obviously.

Comfy Travel Outfit

Day Two – Saturday | Otesaga Drinks + Dinner at Toscana

The Plan: Morning is slow—coffee, porch, doing absolutely nothing. Then we get dressed up and head to the Otesaga Hotel for daytime drinks. It’s very East Coast iconic—white columns, lake views, and just enough preppy to feel like a Nancy Meyers character. We’ll sit, sip, and pretend we’re guests, then head to dinner at our favorite spot: Toscana. It’s a little cozy, a little elevated, and it never misses.

{RELATED POST: Coastal Auntie Staples for That Expensive But Laid-Back Look}

The Look: This is my unofficial start-of-summer outfit. I’m going for something breezy—a linen midi dress with a deep V-neck, paired with bright red mesh flats that are cute enough for a photo and chill enough for wandering the lawn. I’ll drape a navy sweater over my shoulders for daytime, and it’s perfect to throw on later at dinner. Finishing it off with a small red purse for that pop.

Unofficial Start of Summer Outfit

Day Three – Sunday | Boat Day

The Plan: We head out early for our big boat day—snacks, drinks, sunscreen, the whole thing. The lake’s quiet in the morning, which makes it feel extra special. We float, maybe swim, definitely snack, then cruise to Blue Mingo Grill for a late lunch. Afterward, it’s back home to change into something comfy and relax on the lawn with wine and more snacks, obviously.

The Look: A white bikini layered under a striped button-down and classic denim shorts. I’m wearing my Tkees nude leather flip-flops, big sunnies, and a claw clip—easy, effortless, and boat-day approved.

Boat Day Outfit

Day Four – Monday | Drive Back to the City

The Plan: Last porch coffee, one last walk around the house, and then it’s back to reality.  We usually leave late morning, stop for snacks or hit a diner on the way, and start the slow shift back into city mode. Bittersweet, but also kind of nice.

{RELATED POST: 8 Lazy Day Approved Lounge Outfits}

The Look:Comfort’s the priority, but I still want to look put-together enough to hit the grocery store or jump into work once I’m back. I’m wearing a relaxed cotton midi skirt with a cropped white tank, a cream cardigan layered on top, and simple flats to keep it easy but polished.

Travel Day Outfit

More Memorial Day Outfit Ideas

Memorial Day Outfits That Just Get It

From comfy road trip fits to coastal sundresses and lake-ready boat outfits, Memorial Day weekend is basically the soft launch of summer style. Whether you’re heading upstate, Montauk or Cape Cod, or doing a casual hang in your backyard, the vibe is easy, effortless, and just a little bit curated.

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