What I Wore on My Beach Vacation: Chic Outfits for Women Over 50

Well, friends, if you’ve ever wondered what it’s like to wrestle a suitcase full of dresses, a beach bag bigger than your first car, and a husband who wants to leave yesterday, this post is for you! Joe and I packed up and headed to the beach for some much-needed sunshine, seafood, and a chance to wear something other than sweatpants. And let me tell you, I was determined to look cute while not melting into a puddle of sunscreen and humidity.

So grab your iced tea, settle in, and let me show you the outfits that kept me feeling chic, covered, and (mostly) wrinkle-free, because we all know one wrinkle-resistant item in the suitcase does not a wrinkle-free vacation make!

Dinner Out on the Town: Classic Layers and Easy Polished Vibes

For one of our dinners in town, Joe and I decided to put on something a little more polished, because as much as I love a breezy sundress, sometimes it feels good to dress up just a smidge. Joe looked downright dapper in his Wrinkle-Free Performance Gironde Shirt (a mouthful, but it sure looked sharp!) paired with his favorite TravisMathew Black Wanderlust Shorts and a pair of Cole Haan Pinch Tassel Loafers. He looked so good, I almost made him spin for me in the hotel hallway, almost.

• Wrinkle-free shirt stays crisp straight out of the suitcase
• Performance fabric breathes easily on warm nights
• Shorts he can dress up or down without looking sloppy
• Loafers that add instant polish for dinners or date nights

I wore my Linen Cotton Shell, which was breezy and breathable but still structured enough to feel elevated, layered with my Linen Blend Travel Ruana that draped perfectly and added a little movement when the ocean breeze picked up. Paired with my ‘Ab’Solution High Waist Jeans, which tuck everything in nicely without feeling like I’m in a corset, and finished off with Bamboo Thong Sandals, this outfit was my sweet spot between comfort and looking like I had my act together.

This was the perfect outfit combo for a sunset dinner by the water, where Joe kept trying to get me to share my dessert, and I kept politely refusing.

• Linen cotton shell keeps things cool while looking chic
• Linen blend ruana adds stylish layering, flow, and a touch of drama
• High-waisted jeans offer stretch and a smooth silhouette
• Bamboo sandals are lightweight, easy to walk in, and beach-appropriate
• Perfect balance of classic pieces with casual comfort

Joe’s Dinner Look: The Man, The Myth, The Wrinkle-Free Legend

Our first night there, Joe put on this Basketweave cotton Polo sweater from J.Crew Factory and strutted out like he was auditioning for a resort magazine cover. I swear, I almost asked him for his autograph. He paired it with his trusty TravisMathew shorts, he owns more pairs of these than I have patience when I’m hungry.

He looked so polished that I half-expected the waiter to ask if he’d like to sample the wine before bringing it to our table.

• Lightweight, breathable cotton is perfect for warm evenings by the water
• Subtle texture that says “I tried” without looking desperate
• Goes from dinner to sunset stroll without missing a beat
• True-to-size fit that keeps him comfortable and me impressed

Great for: Dinner dates, travel photos, or anytime you want to look put together without trying too hard.

The Dress That Made Me Feel Like a Million Bucks

Ladies, you know that feeling when you put on a dress and you know that it is a keeper? This is how I felt about the 3/4 Puff Sleeve Green Printed Maxi Dress. We went straight from a day of exploring to dinner without a wardrobe change, and I felt like I was floating into every room (or maybe that was the sangria).

The tiered skirt swishes so prettily with each step, and the sleeves give a little coverage for arms that haven’t seen a dumbbell in a hot minute. The subtle print keeps it interesting but not overwhelming.

• Flowy, feminine shape that lets you eat dessert without fear
• Breezy fabric so you don’t sweat more than necessary
• Sleeves that politely cover your arms without making you overheat
• Print that’s lively without screaming “look at me!”, unless you want it to

The little Straw Clutch is a warm-weather staple. The straw texture adds a summery vibe, and it’s the perfect size to tuck under your arm or carry by hand. It’s lightweight but big enough for your phone, lipstick, and keys.

Why it works: Balanced proportions, forgiving shape, and soft structure. You feel pulled together, but still comfortable enough to move and enjoy your day.

Bright and Blooming: Floral Cap Sleeve Midi Dress

The morning I wore this Floral Cap Sleeve Midi Dress, Joe and I decided to wander through beach shops. This dress was perfect. The bold flowers made me feel alive, the cap sleeves gave just the right coverage, and the skirt swished dramatically every time I spun around to show him something he didn’t ask to see.

I sized up to a large so it felt relaxed and easy, no sausage casing vibes here, thank you very much.

• Happy floral print that brightens even cloudy beach days
• Cap sleeves that keep you cool without sacrificing coverage
• Tiered skirt is perfect for impromptu dance moves
• Easily goes from shopping sprees to seaside dinners

These Two Strap Wedge Sandals are a wonderful option when you want a little height without sacrificing comfort. The double straps keep your foot secure, and the cushioned insole makes them wearable for hours. The neutral color goes with everything, and the wedge heel adds length to your legs in the most flattering way.

Why it works: The tiered silhouette skims the body gently without clinging, and the length hits at a flattering spot below the knee. Perfect for those who want to feel stylish but still covered.

Joe’s Casual Looks: Cool Enough for Him, Easy Enough for Me

Joe rotated his Wrinkle-Free Printed Damaschino Polo from UNTUCKit with his Travis Matthews Black WANDERLUST SHORTS, and I swear I’ve never seen him get dressed so fast. We’d wake up, he’d throw these on, and before I could finish my coffee, he’d be asking if I was ready to go. These pieces were perfect for our late-night dinners (where we pretended calories didn’t count on vacation).

• Wrinkle-free polos that look crisp straight from the suitcase
• Shorts that somehow go with everything
• Light, breathable fabrics, perfect for warm coastal evenings
• Simple styles that let him feel relaxed and me feel proud

Great for: Casual dinners, vacation outings, or even casual Fridays at work.

Casual Lunch Date With The Hubby

Joe and I enjoyed a casual lunch at Barefoot Landing. It was wonderful to sit on the patio while watching the boats drive by.

The Stripes That Had Me Feeling Snatched: Short Sleeve Midi Striped Dress

I wore my Short Sleeve Midi Striped Dress, and despite the horizontal stripes, it somehow worked magic by balancing things out instead of making me feel wider. There’s something about a well-cut striped dress that makes you feel pulled together, even when I’m trying to keep up with Joe, who’s already halfway to the next shop.

This dress was cool, comfy, but I would have liked it a little better had it been a tad bit shorter. Add my Straw Clutch for holding the essentials (hotel key and lip gloss) and Crocs Toe Loop Sandal Flats for painless exploring.

• Horizontal stripes that add playful nautical charm
• Soft, breathable fabric for all-day comfort
• Hits below the knee, offering modesty with easy movement
• Versatile enough for coffee runs, shopping, or dinner

Linen-Blend Sleeveless Mini Dress: My Secret Weapon for Surprise Breezes

I wore this Linen-blend sleeveless mini dress with my Summer Patchwork Crinkle Topper on a day the forecast said “sunny” but the ocean breeze said, “hold my drink.” This combo kept me cool when the sun came out and cozy when the wind picked up. I added Drop Earrings and my Pebble Drop Necklace, because an outfit isn’t finished until you add jewelry.

• Linen-blend keeps you cool while looking polished
• Sleeveless cut, perfect for layering or wearing solo
• Crinkle topper adds color, coverage, and a bit of sass
• Accessories instantly dress it up for lunch or shopping

Swimsuits That Gave Me the Courage to Take Off the Cover-Up

I know, swimsuits are tricky at any age, but these made me feel confident enough to strut, okay, cautiously walk, to my lounge chair. The Bloom Ruffle One Piece Swimsuit had tummy control without feeling like medieval armor, and the ruffle neckline felt flirty without going overboard. The Como woven straw tote finished the look and made me feel pulled together, even if I was only carrying snacks, sunscreen, and Joe’s sunglasses.

• Tummy control that smooths without strangling
• Necklines that flatter without plunging
• Soft, quick-drying fabric for endless comfort
• Cover-ups that feel as cute as the swimsuits themselves

Sleek and Supportive: The Jena One Piece Swimsuit

You know those days when you want a swimsuit that makes you feel like you could hop on a yacht, even if you’re just heading to the hotel pool? That’s exactly how I felt in this Jena One Piece Swimsuit. This suit hugs in all the right places, gives a little extra support where we appreciate it most, and has a timeless look that makes you feel like you’ve got it all together.

The wide straps stayed put, the fabric held everything nice and secure, and the simple yet sophisticated cut made it perfect for reading a book by the pool without worrying about adjusting things every five minutes.

• Wide straps that stay put no matter what the breeze is doing
• Classic cut that flatters without feeling skimpy
• Supportive fit that’s comfy enough for all-day lounging
• Timeless style that never looks dated

Pop of Pink: The Tankini That Made Me Feel Fun and Fabulous

I don’t know about you, but sometimes I just want a swimsuit that says, “I am here to have a good time!” This hot pink Tankini Tummy Control Swimsuit did exactly that. The bright, happy color lifted my spirits the second I put it on, and the tummy control made me feel secure without worrying about what was jiggling underneath.

The longer tankini top gave great coverage, especially on days when I didn’t want a one-piece but also wasn’t feeling brave enough for a bikini (which, let’s be honest, is most days). Paired with my Crocs Toe Loop Sandals, I felt playful and polished all at once.

• Easy to mix and match with cover-ups or shorts
• Vibrant hot pink color that screams “vacation mode”
• Tummy control for a smooth, confident silhouette
• Tankini length offers great coverage without sacrificing style

The Swimsuit-and-Ruana Combo That Made Me Feel Fancy

One of my favorite moments on this trip was when I slipped into my Crossover One Piece Swimsuit and threw on my Placed Paisley Duster, and suddenly felt a little extra fancy. The crossover neckline gave a flattering fit without showing too much, and the ruana floated behind me like I had my own personal wind machine (I didn’t, but a girl can dream).

Joe even said I looked fabulous, which is high praise coming from a man who thinks khaki shorts are “fancy.”

This pairing was perfect for feeling covered when walking to the pool or ordering drinks at the beach bar, but light and breezy enough to keep me cool when the sun was doing its best to turn me into a lobster.

• Crossover neckline that supports and flatters the bust
• Tummy control that’s comfortable for long beach days
• Ruana adds drama and coverage without bulk
• Easy to slip on and off between the room and the water

Confidence is the Best Vacation Souvenir

After a week of salty breezes, sandy toes, and sunsets that looked hand-painted, I realized yet again that style doesn’t have to be complicated. It just needs to make you feel good in your skin, whether that’s in a floaty dress, a breezy swimsuit, or a classic pair of shorts. Packing the right pieces let me focus on what mattered most: memories with Joe, moments of peace watching the waves, and laughing until my sides hurt.

So tell me, what outfits make you feel unstoppable on vacation? Share your go-to pieces in the comments below, I’d love to swap stories!

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Matthew 5:10 (NIV)
¹⁰ Blessed are those who are persecuted because of righteousness,
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