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25 Best Resort Wear Pieces To Pack for Your Next Beach Vacation

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You’ve done it! You’ve made it through the dredges of winter, with its snow, sleet, and frigid temps — not to mention, a pandemic that kept most of us at home for a year. Now, with the Covid-19 vaccine available to more people every day and life slowly returning to some semblance of normal, you’re more than ready to take that vacation you’ve been dreaming of. There’s just one teensy, tiny little problem: It practically requires a whole new wardrobe! Not to worry, though — we’ve rounded up the best resort wear for women over 50, so you can enjoy your well-deserved vacation in style. We found flattering, comfortable pieces you’ll love, from hats and sunglasses to swimsuits and sandals. Keep scrolling to shop our picks — we’ve practically made your packing list for you, so all you’ll need to focus on is having fun in the sun!

Deals On Best Resort Wear for Women Over 50:

The Best Resort Wear for Women Over 50

What is resort wear?

Also known as “cruise wear,” resort wear is exactly what it sounds like: Summer-ready, lightweight, packable clothing that you can wear on vacation. Pieces are typically made from breathable materials, such as cotton, silk, straw, and microfiber, while patterns tend to be either bright and fun, like you’d see on a Hawaiian shirt, or classic, such as nautical print.

How should I dress for a resort?

It’s your vacation, so you should dress however makes you happy! That said, if you’re headed someplace sunny, you’ll probably want several swimsuits, a few swim cover-ups, a sun hat, and sandals. You’ll also want some lightweight, flowy dresses, pants or skirts, and tops. Make sure you have at least one outfit that feels fancy enough to wear out to a nice dinner, and plenty of pieces that are easy to pair and wear anywhere your adventure happens to take you.

What’s the best resort wear for women over 50?

Since resort wear shows off a lot more skin than, say, your comfy winter sweatpants, you’ll want pieces that are supportive, comfortable, and of course, stylish.

While some women over 50 will be more than happy to show off their bodies in an itsy-bitsy bikini and shorts, others may prefer pieces with a bit more coverage. One-piece swimsuits or tankinis (Buy from L.L. Bean, $69.99), which have an elongated, tank top-like cut, are slightly more conservative. You can also throw a cover-up (Buy from Anthropologie, $88) over your suit for a bit of added modesty and sun protection.

Cropped pants or shorts with a 7 or 5-inch cut (Buy from Tommy Bahama, $79.50) will keep you cool without riding up your backside, and oversized hats will keep aging skin safe from the sun’s harmful rays.

Regardless of your age, however, the best resort wear will consist of the pieces you feel the most attractive and confident in. We’ve chosen a wide selection of breezy finds that will be suitable for whatever activities your vacation may bring, whether you’re strolling the beach or lounging in a hammock.

Ready to trade in your winter boots for flip flops and your sweaters for tunics? You’ve come to the right place. Keep scrolling to shop our picks for the best resort wear for women over 50.

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The Best Resort Wear For Women Over 50

The Positano Resort Dress

Best sundress for women over 50
kenny flowers positano dress
Kenny Flowers
20% off!

Buy from Kenny Flowers, $158 — Use code KF20 for 20 percent off all orders sitewide! For orders of $300+, use code KF30 for 30 percent off! Plus, free shipping on orders over $125!

Why we like it:

  • Fun lemon print
  • Customizable straps
  • Organic material

Whether you’re walking on the beach or grabbing a quick bite while you see the sights, no one will be able to take their eyes off you in this number! The Positano Resort Dress from Kenny Flowers will instantly make you (and everyone else) smile when you slip it on. We’re not sure what we love more: its bold and cheerful lemon print, or the 100 percent organic rayon material. However, we’re sure you’ll be as obsessed with it as we are. The dress features adjustable straps that can be tied or tucked inside, and it’s ethically made. Pair with your favorite sandals, and prepare for all the compliments.

BeanSport Swimwear High-Neck Tankini

Best resort tankini for women over 50
Best Resort Wear for Women Over 50
L.L. Bean

Buy from L.L. Bean, $54.99

Why we like it:

  • Features a slimming fit
  • Can mix and match with coordinating bottoms
  • Included soft cups provide support

Modest is far from frumpy in this eye-catching L.L. Bean tankini, which covers your tummy without sacrificing an ounce of style. It’s got soft cups for shaping and support and detailing at the neckline for a bit of added flair. Pair it with the bottom of your choosing — we like the mid-rise skort featured below the top, which has a higher leg line and a more modest rear.

Promising review: This suit is not only beautiful but makes you feel slimmer, which is what I was looking for! I am slowly losing weight but I felt really good about my belly not being a distractor. 100% more confidence in this suit! I also got the cute skirt to go with it……love it!

Look Into The Sun Maxi Dress

Best halter dress for women over 50
Best Resort Wear For Women Over 50
Free People

Buy from Free People, $98

Why we like it:

  • Adjustable
  • Sexy
  • Low slit

Summer is the time to show some skin, and it doesn’t get much sexier than this gorgeous halter dress. The Look Into The Sun Maxi is the perfect blend of elegant and fun, making it a great option for nights spent dining and dancing. Although the flowy bottom looks airy light, the material is substantial enough to keep everything in one place if a breeze comes your way. The top is adjustable, and there are some subtle slits on the side. Flattering to both small chested ladies, as well as the busty, you’ll love how the rayon material skims your curves.

Editor’s review: “I love a halter dress! They’re universally flattering to all bust sizes. I also love a maxi, and was pleasantly surprised by the weight of this one. Some dresses with a guazy look feel really flimsy, but not this one! I could feel the quality as soon as I tried it on, and I know I’d be comfortable wearing this to a fancy summer wedding or resort restaurant. I tried a small, and it fit great. I don’t have much in the bust department, so I really appreciated how I could adjust the straps and cups to cover me. You don’t need a bra with it, but I still think I’ll invest in some push-up pasties when I wear this out on the town. The dress is long, and even with my 3.5-inch heels the back dragged, so unless you’re very tall (I’m five-foot-five), you may want to have it hemmed. Is it worth it? Uh, yes! It’s simply too lovely to pass up.”

Alex Evens Tie Waist Mesh Pants

Best wide leg pant for women over 50
Best Resort Wear for Women Over 50
11% off!

Buy from Amazon, $75.80 (was $85)

Why we like it:

  • Relaxed fit
  • Bright beachy color
  • Stretchy

Don’t box yourself in on holiday. Instead, opt for this roomy wide-leg pant from Alex Evens. It’s perfect with a bikini top, tee, or tank. Made with air chiffon, you’ll love how breathable these pants are. Hitting right above the ankle, they won’t drag on the pavement while you sightsee or become damp from walks on the beach. Although relaxed, they slightly come in at the waist, which gives them a look that’s still tailored. Wear them as you lounge by the pool, grab drinks, or even on the plane ride home.

Eric Javitts Squishee Classic Fedora

Best Sun hat for women over 50
Best Resort Wear for Women Over 50

Buy from Bloomingdale’s, $285

Why we like it:

  • Classic look
  • Goes with many different looks
  • Sun protectant

Floppy sun hats are great, but Fedoras are a bit cooler. Take the Squishee Classic Fedora, for example. Its brim is just under three inches, so it will protect you from the sun without hiding your gorgeous face. No matter if you wear it with a sundress, swimsuit or shorts, you’ll look classically stylish. Best of all, even when your vacation is over, you’ll be able to wear it out on the town. Throw it on when running errands or for a lunch date. You’ll turn heads and get compliments. The design is packable — perfect for getaways — and has a timeless black ribbon above the brim. Available in cream or tan.

Promising review: “This hat was chosen to wear to a wedding in a very hot climate. Not only did it look amazing, but it provided protection from the sun and disguised any hair imperfections from the humidity. I felt composed and confident. On my flight to Oklahoma, I was asked repeatedly where I purchased it and the designer. The fit is perfect, feels comfortable and is worn with ease, which I find necessary when wearing a hat. I am grateful to have found it. It will be a part of my wardrobe for many years.”

Soft Slub Boyfriend Capri

Best plus size capri pants for women over 50
Best Resort Wear for Women Over 50
Lane Bryant
Great price!

Buy from Lane Bryant, $14.98 (was $69.95)

Why we like it:

  • Available in lots of colors
  • Great for multiple seasons
  • Lightweight

When the weather warms up you want a pair of pants that don’t make you sweat, but can be worn in different ways. What we love about these boyfriend capri pants from Lane Bryant is that they’re just the right blend of tailored and relaxed, hitting a little below the mid-calf and cuffed. Available in several neutral earth tones, these ultra soft pants have a drawstring tie to avoid gaping (we hate that), and are made with a cotton-blend fabric. Pair these with a tee and jean jacket, blouse or cable knit sweater. You can wear these in spring, summer, and even fall. Don’t be surprised if you decide to snag several pairs. They start at size 10/12 and go up to 26/28.

American Optical General Sunglasses

Best resort sunglasses for women over 50
Best Resort Wear for Women Over 50
American Optical
Editor's favorite!

Buy from Amazon, $219.95 (was $244)

Why we like it:

  • Customizable
  • Smudge resistant
  • Reduces eye-fatigue

Keep your peepers safe and your look chic with these classic sunnies. Since 1833, American Optical has been the ultimate crafter of eyewear, and their creations have been a favorite of movie stars and visionaries alike. We know you’ll feel like A-list royalty when you show up to the resort in a pair of the General Sunglasses. They have the perfect aviator shape, and make every wearer look sophisticated and cool. I love them in rose gold, but you can snag them in regular gold, or silver. Customize the look and fit on their website, where you can upload a shot of yourself to get a truer feel for how you’ll appear once you are sunning yourself poolside. The glasses offer full UVA and UVB protection — the most important thing — and the lenses are scratch resistant and have a smudge resistant coding to keep them in tip top shape.

Editor’s pick: I’m really impressed by these sunglasses from American Optical. I’ve always wanted a pair of aviators, but could never find the right ones. These fit my face perfect, and give me that downtown cool girl vibe I’m always chasing. I can wear them with anything — dresses, jeans, sweats…you name it! I look instantly put together. They’re distortion free, which I love for when I’m driving. Plus, they come in a very sturdy, very nice case.

London Rag Diyora Espadrille Platform Sandal

Best wedged heel sandals for women over 50
Best Resort Wear For Women Over 50

Buy from DSW, $49.99

Why we like it:

  • Ribbed rubber bottom
  • Comfortable height
  • Adjustable closure

We’re obsessed with the Liza Espadrille Wedged Sandal from Dolce Vita. It gives just enough height to elongate the leg, while remaining comfortable enough to wear all day. The bottom has ridges, and basically performs like a sneaker. The adjustable straps keeps you from sliding around as you jet from one spot to the next. They’re fancy enough to wear with a sundress or skirt, but also will liven up a pair of shorts or pants. Available in several classic colors, you’re not going to want to take a vacation without them.

Promising review: “I bought these for a trip down to Florida and! I love them! They are super sturdy for walking, and they’re also super comfy!”

No Iron Knit Mix Tunic

Best resort tunic for women over 50
Best Resort Wear For Women Over 50
Price drop!

Buy from Chico’s, $99

Why we like it:

  • Pullover style
  • Doesn’t wrinkle
  • Can be worn year round!

This No Iron Knit Mix Tunic is perfect for travel. To begin with, every lady needs a fresh white shirt, and this relaxed tunic is breathable, packable, and can be worn lots of ways. Pair it with chinos, shorts, or a skirt for a put-together look that’s still comfortable enough for hot weather. When you return home, add a blazer and your favorite pencil skirt and heels. Happy customers at Chico’s suggest sizing down.

Promising review: “I just received this. It is stylish, crisp and comfortable, and I can tell it will become a staple in my wardrobe. It’s waiting patiently in my closet to go to Italy next week. It looks great with a pencil skirt, jeans or black pants.”

Craftsman Rattan Adjustable Crossbody Bag

Best crossbody bag for women over 50
Best Resort Wear for Women Over 50

Buy from Amazon, $25.89

Why we like it:

  • Lightweight
  • Perfect for carrying essentials
  • Handmade

No one wants to carry a heavy bag when out on the town. This light, handmade rattan crossbody bag is perfect for day excursions and relaxed dinners. Crafted by Vietnamese artisans, the bag’s strap is adjustable and perfect for carrying your wallet, phone, and room key. It has a button closure, and is lined with linen to keep your valuables scratch free. Toss your bracelets or necklace inside if you take a dip in the pool. They wont become entangled by the natural fiber. This goes great with a sundress, pants or shorts, but can also be worn with a little LBD to make your look more modern or downtown chic.

Promising review: This small bag is super comfortable, and spacious. I love that every time I wear it I get compliments. It’s trendy but also classic. The price is incredible compared to others on the market. I usually have a hard time finding a small bag that fits my large cellphone, and this one does!

Ann Taylor Linen Cotton Pocket Shirtdress

Best causal resort dress for women over 50
Best Resort Wear For Women Over 50
Ann Taylor

Buy from Ann Taylor, $39.88 (was $149)

Why we like it:

  • Can be worn for work and play
  • Quarter length sleeves
  • Flowy

It can be really frustrating to buy clothes that work for vacay but not everyday life. Fortunately, that’s not an issue with this flowy number. The Linen Cotton Pocket Shirtdress is perfect for causal sightseeing strolls, but can also be worn to work or an evening with friends. It comes in every-so-gently at the waist, and remains relaxed enough for you to remain comfortably cool on the hot days. If you’re self-conscious about your arms, you’ll love the sleeves. Plus, the dress has pockets! You can pair this lovely dress with a pair of wedged sandals, but I’d even wear it with ice white sneakers, and cardigan.

Michelle Tunic Cover-Up

Best beach top for women over 50
Best Resort Wear for Women Over 50
25% off!

Buy from Nordstrom, $94

Why we like it:

  • Relaxed, flowy style
  • Button-down V-neckline
  • Also comes in black

We think this breezy garment from Nordstrom could easily double as the perfect beach top. Flowy and loose, with a flattering button-down V-neckline, you’ll feel light and free, while the gauzy design adds some coziness for breezy shoreline walks. We also love that it’s available in four neutral colors!

Promising review: “This shirt was exactly as expected. Very oversized and comfy. Good for lounging around the house or even [as] a beach cover up.

The Sidestroke

Best stylish swimsuit for women over 50
best stylish swimsuit

Buy from Amazon, starting at $95

Buy from Summer Salt, $47.50 (was $95) – 50% off!

Why we like it:

  • Asymmetrical design
  • 11 shades to choose from
  • Editor favorite

People rave about this fun and flattering asymmetrical colorblock suit. A perennial bestseller, it offers full bust support and coverage for your derrière and comes in a long-torso version as well. Available in nine color combos (including solid black for a more classic look), your biggest problem will be choosing just one! 

Promising review: So not only is this beautiful swimsuit comfortable and aesthetically gorgeous but it is so flattering. I’ve never felt so comfortable in a swimsuit. Not worried about my boobs popping out or having to tuck them in. The suit is very formfitting but not in a uncomfortable way. Keeps everything in its place.

Coral Stretch Knit Walking Shoes

Best resort sneaker for women over 50
Best Resort Wear for Women Over 50
Price drop!

Buy from Ortho Feet, $119.95 (was $142.95)

Why we like it:

  • Great for diabetics
  • Flexibility
  • Lots of color options!

If you’re going to view local attractions, you need a good pair of sneaks! Take these Walking Shoes, for example. Along with coming in a variety of colors, they’re also engineered to support your arches and heel. Your feet won’t get funky, thanks to their anti-microbial fabric and foam, and they’re flexible enough to move with your natural stride pattern. They’re a great option for those with diabetes, bunions, or even plantar fasciitis. More importantly, they’re amazing if you have a full day of museum hopping and clothes shopping planned. Available in standard and wide, you’ll wear these even when vacation has ended.

Promising review: “Love these shoes! Comfortable from day one, and they’ll come in handy for my trip to California!”

Bluetime Women’s Chiffon Maxi Skirt

Best guazy resort skirt for women over 50
Best Resort Wear For Women Over 50
20% off!

Buy from Amazon, starting at $9.88

Why we like it:

  • Flowy
  • Available in different prints
  • Goes up to XXL

This gorgeous skirt from Bluetime doesn’t only work for vacay but home. When the days are warm it looks lovely with a pair of sandals and cami. On cooler afternoons it can be worn with tights, boots, and a sweater. The flowy skirt features an elastic band for comfort, and is made from lightweight chiffon. Plus, the price is amazing. We’d buy more than one, especially since it’s available in a variety of prints.

Torry Large Canvas Shoulder Bag

Best beach tote for women over 50
Great deal!

Buy from Amazon, $22.78

Why we like it:

  • Lots of pockets!
  • Oversized design fits most beach supplies
  • Features a cute pom pom and rope handles

Between your sunscreen, lip balm, poolside snacks, towel, and beach reads, you’ll be needing plenty of room in your vacation tote, and this large canvas bag affords it — and then some. Two exterior and three interior pockets allow you to find what you need in a jiff, while nautical-rope straps and a striped pattern lend themselves to the laid-back atmosphere.

Promising review: I love this little tote bag. I purchased it for a weekend in Lake Havasu and it was perfect! It fit my large towel, all my sunscreens and my flip flops and still had tons of room! I also love the side pouch for easy access to my water and my phone. The straps are nice and thick which made it comfortable enough to throw over my shoulder since I was carrying a lot of things. I also love that it zips up for privacy. It also cleans really well. One of the girls got bean dip on it and I was able to wash it right off with a little soap and water! Perfect lake/beach bag.

Pha Resort Wear Skirt Long Maxi Skirt

Best beach skirt for women over 50
Great value!

Buy from Amazon, starting at $25.99

Why we like it:

  • Made with soft cotton fabric
  • Has an elastic waistband for added comfort
  • Bright red color adds a pop to your wardrobe

With its easy tiered design and its cotton fabric, this skirt was made for kicking up your heels. It has a comfortable, elastic waistband and reaches down to your feet, covering up any lower body imperfections. This bright red shade will add a pop of color to your beach wardrobe, and is perfect for strolling along the beach while sipping your favorite tropical drink.

Happy customer: Color just like in picture, lovely feel and length.

Woven T-Shirt Dress

Best beach shirt dress for women over 50
Best resort wear for women over 50
40% off!

Buy from Nordstrom, starting at $31.60

Why we like it:

  • Soft material
  • Flowy and breathable
  • Simple yet trendy

If you prefer a more understated style, you can’t go wrong with this maxi t-shirt dress. Designed like your favorite soft t-shirt with a billowy, flowy bodice that drapes past your knees, it’s comfortable, versatile, and plenty fashion-forward, making it your new vacation secret weapon. 

Happy customer: This dress is exactly my style. Dresses are just so great in the heat of the summer. I look to ATM every year and they do not disappoint. Simply the perfect dress for me and the fit is TTS.

Sanibel One-Piece Swimsuit

Best One-Piece bathing suit for women over 50
best resort wear for women over 50

Buy from Amazon, starting from $123.43

Why we like it:

  • Classic look
  • Slimming
  • Adjustable straps

Let’s bring the one-piece back, shall we? Especially if it’s as sexy and flattering as the The Sanibel One-Piece Swimsuit . The stretchy nylon conforms to your curves while slenderizing. The built-in wired cups offers support as you splash in the ocean or pool. It’s recommend that you order one cup size up. The adjustable straps mean you won’t have to deal with material digging into your back or unsightly bulges.

Happy Customer: “This is the second Miraclesuit Sanibel Underwire one piece style I’ve purchased. I am 5 foot three, 150 pounds, and wear a 38D. I love the fit and style. The suit fits snugly, and you will definitely appear 10 pounds slimmer. It really smooths your shape!”

La Blanca Slouchy Hooded Sweater Cover-Up Tunic

Best beach cover-up for women over 50
Great deal!

Buy from Nordstrom, $69

Why we like it:

  • Adjustable drawstring hood
  • Comes in 2 colors
  • Lightweight material

Even paradise can get a little chilly from time to time! Cover up with this oversized sweater from La Blanca, which has a drawstring hood for added warmth and a summer-ready nautical print. Choose from black or midnight blue.

Happy customer: True to size, very comfortable. It’s more than a cover up, you can wear it out and about for those lazy days with tennis shoes. Lounge around the house. I usually wear a small, but if you want a more roomier fit, size up. Will be purchasing the blue one next.

Jezabell 57mm Round Sunglasses

Best resort sunglasses for women over 50

Buy from Nordstrom, $65

Why we like it:

  • Vintage-inspired design
  • Round lenses
  • Can be worn year-round

Dark and alluring, Quay Australia’s upscale Jezabell sunglasses speak to the affluent lifestyle resort wear, and were originally created to accommodate while remaining relatively reasonable in the price department. Old Hollywood glamour, anyone?

Promising review: Alas! A pair of sunglasses that can be worn on a daily basis and I don’t feel like I need to be dressed up to wear them. Also, they fit my big head and are extremely comfortable to wear (no digging on the bridge of my nose or behind my ears!) For reference, I have a square-shaped head and these glasses suit me well! You also can’t beat the price! I own a range of sunglasses from a bunch of different designers and these, by far, are the best I’ve ever owned!

Tory Burch Miller Sandal

Best flip-flops for women over 50
Best Resort Wear For Women Over 50
Price drop!

Buy from Nordstrom, $198 (originally $228)

Why we like it:

  • Made with soft leather
  • Perfect for a minimalist style
  • Available in different colors

Comfort is key when you’re trying to relax — particularly when it comes to footwear. Invest in a pair of luxe flip flops, like this leather pair from Tory Burch, that will get you through every activity on your itinerary. Their clean, minimalist aesthetic will pair well with the rest of your resort wardrobe, wacky patterns included.

Happy customer: I bought this shoe in the vintage vachetta leather and I love them! The color is a great brown neutral. The shoes are comfortable and non-blister inducing.I like the fact that while this shoe has a large logo, it blends in with the rest of the shoe without being straight up in your face and can still just look like a pretty design. I would say these shoes run pretty true to size but if between sizes, I would go with the bigger of the two just because I hate too small looking sandals where toes or heels hang over. 

Tommy Bahama Boracay 5-Inch Shorts

Best resort shorts for women over 50
Tommy Bahama
Great deal!

Buy from Nordstrom, $79.50

Why we like it:

  • Come in a 5-inch cut
  • Made with cotton material
  • Available in 7 colors

For a breezy pair of shorts with a longer cut, we love these Boracay bottoms from Tommy Bahama. Not only do they hit at the mid-thigh, thanks to a comfortable 5-inch cut, they’re made of a mostly cotton fabric with a hint of stretch for added ease. A khaki color, like the pictured pair, will also go with just about anything you happen to pack.

Happy customer: These Boracay shorts are the most soft and comfortable shorts I’ve ever owned. I’ve bought different types from a variety of stores and these are far, far better. The quality of the material is amazing. I won’t buy shorts any where else. I love all the colors I ordered. I am beyond satisfied.

Roller Rabbit Dakota Maxi Dress

Best maxi dress for women over 50
Best Resort Wear For Women Over 50

Buy from Anthropologie, $119.95

Buy from Amazon, $198

Why we like it:

  • Romantic scoop neck
  • Relaxed flowy design
  • Features fun florals and polka dots

If you need a little extra coverage in the swimwear department, look no further than this Anthropologie cover-up, which offers just a hint of what lies beneath without baring it all. Its slouchy fit offers a relaxed appearance so you can easily just throw it on and go. Adjust the straps for your ideal fit and try not to be obsessed with the fun floral. The popular dress is always being released in new patterns, so if you’re not crazy about this one, keep checking back for its latest edition. You can also find the maxi on Amazon!

Happy customer: “Oh so comfy. Dress is tight in the bust (true to size) and flowy below it… Perfect for hot summer days. The patterns are even more beautiful in person.”

Wandering Soul 2 Wide Leg Pants

Best beach pants for women over 50
Best Resort Wear For Women Over 50

Buy from Nordstrom, $55.95

Why we like it:

  • Extra-wide leg design
  • Adjustable drawstring waist
  • Breathable material

Flowy and ventilated with an extra-wide leg and a slit on either side, these flouncy pants are exactly what we want to be wearing on our next seaside venture. There’s a drawstring waist for a custom fit and a bit of intricate detailing at the edges. 

Happy customer: I loved these pants! They were comfy and a perfect cover up for being poolside and still looking chic. I usually wear a large and ordered a large but probably could have gotten a medium. I like the loose fit though.”

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