Memorial Day Weekend: Summer Style Starts Here (and a Moment to Remember)

There’s a particular quiet that settles over my house on Memorial Day morning — before the grill gets going, before the screen door starts slapping with family running in and out (although rain and more rain are in the forecast), before the coolers come up from the basement. I like to take that quiet and sit in it for a minute, because somewhere underneath the long weekend and the white pants and the first real swim of the season, there is a reason this Monday exists at all.

Memorial Day isn’t about the sales, much as I’ll happily share a few good ones with you below. It’s the day we set aside to remember the men and women who died serving this country — the ones who never got their own long weekends, their own first swims, their own children slapping the screen door.

My own father was a proud Marine, and some of my earliest memories are of him patiently teaching me the Marines’ Hymn, line by line, “From the halls of Montezuma to the shores of Tripoli,” until I could sing it from memory. I still can, all these years later; the words come back the moment I think of him. That’s what remembering looks like, I think. Not something grand. Just a name, a song, a story carried forward and handed down. So before we talk swimwear and summer outfit formulas, I want to ask you to do what I’ll be doing: pause, even for a breath, and remember someone. Fly the flag if you have one. Teach a grandchild a name. That’s the whole assignment, and it matters more than anything else on this page.

And then — because they fought, in part, so we could have ordinary, beautiful days — let’s go have one. Memorial Day is the unofficial kickoff to summer, and around here, that means it’s time to talk about the clothes that carry us all the way through to Labor Day. Pour yourself something cold (might I suggest a frozen frosé?) and let’s get into it.

What to wear for Memorial Day weekend over 50

Here’s the short, honest answer if you’re skimming: for Memorial Day weekend and the summer that follows, you want one great swimsuit you actually feel good in, a lightweight cover-up that doubles as a real outfit, and the easiest formula in the world — a button-up shirt and a skirt — that you can rearrange a hundred different ways through August. Get those three things sorted, and you’re dressed for 60% of summer, from the pool to the patio to the farmers’ market. Everything below is just me walking you through the how.

Style has no expiration date, Grit & Glammers — and neither does feeling like yourself in a swimsuit. Let’s start there.

The summer swimsuit that actually feels good

I will be honest with you, the way I’m always honest with you: somewhere in our forties or fifties, a lot of us quietly decided the swimsuit chapter was closing. We started reaching for the cover-up before we’d even tried the suit. And I understand it — I do — but I’d like to gently retire that habit, because the right suit changes everything and Lands’ End is a great brand for swimwear.

What I’ve learned after a decade of trying these things on so you don’t have to: fit beats coverage every single time. A suit that supports you where you want support, sits right at the waist, and is cut in a fabric with a little structure will always look more polished than a suit that’s simply trying to hide. The striped two-piece I’m wearing here is a high-waisted set — full coverage through the middle, a supportive band on top — and I felt completely like myself walking out to that pool. That’s the bar. Not “does this hide me” but “does this feel like me.”

If you’re petite, the fit conversation matters even more because proportion is everything on a shorter frame. Kelly went deep on this in her full guide to the best swimsuits for petite women over 50 — which straps, which rises, which cuts lengthen rather than cut you in half — so if that’s you, start there and come back.

A few of my hard-won swimsuit truths:

• High-waisted bottoms are your friend. They smooth, they support, and they pair beautifully with a cropped or banded top.
• Look for a real band or underwire up top. Support isn’t about age — it’s about comfort, and comfort is what lets you stop thinking about the suit and start enjoying the day.
• A classic stripe or solid will outlast every trend. I reach for navy-and-white stripes the way some women reach for their morning coffee — it just always works.

The cover-up that’s secretly a whole outfit

This is the trick that took me years to learn, so let me save you the time: the best cover-up isn’t really a cover-up at all. It’s a crisp white button-up shirt — oversized, long, in a featherweight cotton or linen — that you throw on over your suit at the pool and then keep wearing to lunch, to the market, to the porch at golden hour. You see me doing exactly that in the photo up top: striped suit underneath, long white shirt open over it, a straw tote, flat sandals, sunglasses I can push up into my hair. That’s a full look that took me ninety seconds to assemble, and it’s the same shirt I’ll wear unbuttoned over white jeans next week.

That’s the magic of building summer around pieces that do double duty. Which brings me, neatly, to my favorite warm-weather formula of all.

The easiest summer outfit formula: button-up + skirt

If I could hand every woman over fifty one outfit formula for summer, it would be this: a button-up shirt and a skirt. That’s it. It’s the formula I reach for time and again — a chambray shirt, a colorful patchwork skirt, a woven belt to define the waist, a straw tote, easy flats — and it is endlessly, almost ridiculously, adaptable.

Here’s why it works so well for us, and how to make it your own:

1. Start with the skirt. A short A-line or pencil skirt in a fun print or a clean solid sets the tone. Madras plaid for color, white denim for crispness, a soft midi if you prefer more coverage — all of it works.
2. Add a button-up on top. Chambray for that easy denim-meets-summer feeling, crisp white for polish, or a stripe if you want a little pattern play. Tuck it, half-tuck it, or knot it at the waist.
3. Define the waist. This is the step most people skip, and it’s the one that makes the whole thing look intentional rather than thrown together. A woven raffia belt — like the one I’m wearing — does it instantly.
4. Finish with summer neutrals. A straw tote and a pair of flats or flat sandals, and you are dressed. Add earrings if the mood strikes.

The reason I love this formula so much is that it gives you structure without fuss. You’re not squeezing into anything. You’re not fighting the heat. You’re just pulling two pieces you love off the hanger and trusting them to work — because they will. For more on building a polished summer base, my guide to the best white pants after 50 follows the exact same philosophy: a few great pieces, endlessly remixed.

A note on stripes — and my BeBe uniform

If you’ve followed me for any length of time, you know I have a deep and abiding love of a good stripe. So I have to tell you about the new Frank and Eileen collection, because it has become, quite genuinely, my go-to BeBe uniform — the thing I reach for when my granddaughters are coming over, and I want to look pulled together and comfortable without thinking about it. Soft, beautifully made, striped in that classic way that never tires. If you love stripes the way I do, you’ll want to see this collection.

I recently shared Opening my Porch and Patio for Spring. The post is loaded with great buys from Wayfair.

Memorial Day weekend sales worth your time

Now for the fun part. I don’t share sales unless I’d actually shop them myself, so here’s where I’m looking this weekend:

• Evereve — wonderful for elevated everyday pieces, and a great place to find that perfect striped button-up or summer skirt. Shop the Evereve sale.
• Chico’s — always a strong source for easy summer separates and that waist-defining belt. Shop the Chico’s sale.
• Lands’ End — my reliable stop for swimwear with real coverage and real support, plus those crisp white cover-up shirts. Shop the Lands’ End sale.
• EBY — foundation and swim pieces that make everything else fit better. Shop EBY.
• Frank and Eileen — the new striped collection I can’t stop reaching for. See it here.
• Wayfair — because Memorial Day is also when the patio gets its act together. If you’re hosting this weekend, it’s a good time to refresh the outdoor furniture.

Common questions about summer style over 50

What should a woman over 50 wear to a Memorial Day cookout?

Reach for the button-up-and-skirt formula: a chambray or crisp white shirt, an A-line or pencil skirt in a summer print or white denim, a woven belt to define the waist, and flat sandals or woven flats. It’s comfortable in the heat, looks intentional, and works for everything from a backyard grill to a casual lunch out.

What’s the most flattering swimsuit style for women over 50?

A high-waisted two-piece or a well-structured one-piece tends to be the most flattering, because fit and support matter far more than coverage. Look for a real band or underwire up top and a bottom that sits comfortably at your natural waist. A classic stripe or solid color will outlast every trend.

Can you wear white before Memorial Day?

You absolutely can — the old “no white before Memorial Day” rule has been retired for years. That said, Memorial Day is still the unofficial green light for summer whites, so if you’ve been waiting, this is your weekend. A pair of crisp white pants or a long white cover-up shirt is one of the most useful things you can own all season.

How do you style a button-up shirt over 50?

Think of it as your most versatile layer. Wear it open over a swimsuit as a cover-up, tucked into a skirt with a belt for a polished daytime look, or unbuttoned over white jeans for easy evenings. A crisp white or chambray button-up will carry you through the entire summer.

Let’s make it a beautiful summer

So here’s the whole weekend, start to finish: take a quiet minute to remember the ones who made these ordinary, beautiful days possible. Then fly the flag, fire up the grill, pull on the suit you actually feel good in, throw a crisp white shirt over it, and step into summer like it’s been waiting for you — because it has.

I’d love to know what you’re wearing this weekend, and whether you’re a stripe woman like me. Tell me in the comments — and if you’re hosting, my frozen frosé and grilled veggie flatbread will not steer you wrong.

Style has no expiration date, Grit & Glammers. Let’s go have a wonderful summer.

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