15 Best Resort Wear Pieces for Women Over 50

You'll want to put these on your packing list.


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!

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 cut-offs, others may prefer pieces with a bit more coverage. One-piece swimsuits or tankinis (Buy on L.L. Bean, $89), which have an elongated, tank top-like cut, are slightly more conservative. You can also throw a cover-up (Buy on Anthropologie, $188) over your suit for a bit of added modesty and sun protection.

Cropped pants or shorts with a 7 or 5-inch cut (Buy on 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 find yourself strolling the beach or laying in a hammock.

Ready to trade your winter boots in for flip flops (Buy on Nordstrom, $198) and your sweaters in for tunics (Buy on NYDJ, $59.98)? You’ve come to the right place. Keep reading for Woman’s World picks for the best resort wear for women over 50.

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The Best Resort Wear For Women Over 50

Feeling Groovy Maxi Dress

Best Resort Dress for Women Over 50
Free People best resort wear for women over 50
Free People

Buy from Free People ($168)

Why we like it:

  • Tie front
  • A-line silhouette
  • Beachy-fun pattern

No piece of resort wear is more essential than a chic sun dress, and this maxi-length pick from Free People is as about as perfect as it gets. Not only does it feature an open flowy design that’s sure to flatter nearly any body type, it also has a fun, beach-ready print that’s ideal for all those vacation photos you’re sure to be taking and the tie neck adds a perfect delicate touch. It also comes in four colorful patterns.

Happy customer: Love this dress. Ordered my usual XS and fits perfectly, love the fact of the tie in the back, I am a little bustier and this tie really helps with the overall fit for me. Finally, more cotton pieces coming through Anthro, tired of these fake bad feeling materials.

Eric Javits Bella Floppy Hat

Best Beach Hat For Women Over 50
Bloomingdale's best resort wear for women over 50

Buy from Bloomingdale’s ($295)

Why we like it:

  • 5-inch brim to protect you from the sun
  • 3 neutral colors
  • Foldable for travel

You won’t need to think twice about time spent in the sun with the shade of this classy sun hat, which has a 5-inch brim to keep your face under wraps. It folds down to better fit in a suitcase or travel bag and it also comes in three basic colors including cream, black, and natural for you to glam any beach outfit with.

Happy customer: This hat is exquisite! I’ve gotten endless compliments on the style and quality!

Roller Rabbit Dakota Cover-Up Maxi Dress

Best Resort Cover-Up for Women Over 50
Roller Rabbit cover up maxi dress

Buy from Anthropologie ($188)

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 and polka dot patterns!

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.”

Boston Proper Everyday Side-Zip Twill Capri

Best Lightweight Capris for Women Over 50
Boston Proper best resort wear for women over 50
Boston Proper

Buy from Boston Proper ($59.50)

Why we like it:

  • Four-way stretch
  • High-rise waist
  • Comes in 3 classic colors

We love the classic color of these white four-way stretch capris, which practically scream “vacation.” Also nice? The ultra-wide waistband, which creates a smooth, slimming look, and the high-rise cut that flatters the waist. Enjoy the comfort and stretch of these versatile capris and get ready to wear these out whether it’s for a nice dinner or lounging on the beach.

Happy customer: I’ve been purchasing these same pants for years in every color. They are a perfect staple to every summer wardrobe — a must have. Good quality, they wear well, [and] minimal ironing. I loved the capris so much I got the shorts and love them just as much!

Blouson Tankini

Best Resort Tankini for Women Over 50
L.L. Bean best resort wear for women over 50
L.L. Bean

Buy from L.L. Bean ($89)

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.

Happy customer: 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!

Torry Large Canvas Shoulder Bag

Best Beach Tote For Women Over 50

Buy from Amazon ($30.95)

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.

Happy customer: 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.

Jezabell 57mm Round Sunglasses

Best Resort Sunglasses for Women Over 50
Nordstrom best resort wear 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?

Happy customer: 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!

Maxi T-Shirt Dress

Best Beach Shirt Dress for women Over 50
ATM best resort wear for women over 50

Buy from Nordstrom ($225)

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-shirtdress from Anthony Thomas Melillo. 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.

Popover Tunic Top

Best resort Tunic for women Over 50
NYDJ best resort wear for women over 50

Buy from NYDJ (From $42.98)

Why we like it:

  • Made of linen
  • Has a cute notched collar
  • Long length can be paired with most bottoms

If this linen ruffle tunic doesn’t make you want to jet set away to the tropics, we don’t know what will! Its notched collar, long length, and a look-at-me print are just what the doctor ordered for sipping mai tais and taking in the local fare at your vacation destination. 

Happy customer: I love this top. It fits true to size and is comfortable and looks very good on. it is one of my favorite tops. I might buy another one just to have it for the future. It is a classic style.

Chelsea 28 Ana Smocked Split-Leg Pants

Best Beach Pants for Women Over 50

Buy from Nordstrom ($59)

Why we like it:

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

Flowy and ventilated with an extra-wide leg and a calf-high slit on either side, these smocked gauzy 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.”

Tory Burch Miller Flip Flop

Best Flip Flops for Women Over 50

Buy from Nordstrom ($198)

Why we like it:

  • Made with soft leather
  • Perfect for a minimalist style
  • Various patterns and 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. 

La Blanca Slouchy Hooded Sweater Cover-Up Tunic

Best Cover-Up Sweater for women over 50

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.

Pha Resort Wear Skirt Long Maxi Skirt

Best Beach Skirt for women Over 50

Buy from Amazon ($28.99)

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.

Odetta Embroidered Top

Best beach top for women over 50
Anthropologie best resort wear for women over 50

Buy from Anthropologie ($98)

Why we like it:

  • Billowy sleeves are relaxed, yet elegant
  • Flattering plunging neckline with adjustable tie
  • Colorful embroidery adds a fun touch

We think this boho garment from Anthropologie could easily double as the perfect beach top. Loose with frilly details, you’ll feel light and free, and the brightly-colored floral pattern is sure to turn heads. It also comes in multiple sizes including petite and plus size!

Happy customer: I got this blouse because I love the gorgeous colors, lightweight material and generous sizing which makes it perfect for a rounder shape like mine. The details are just exquisite and it can be worn year-round with jackets in the fall/winter or alone in the spring/summer. The colors will with SO many pairs of pants – jeans, white jeans, and green/purple/blue cropped summer pants (and skirts). Details are everything you expect from Anthro and well worth the price!

Tommy Bahama Boracay 5-Inch Shorts

Best resort Shorts for Women Over 50
Tommy Bahama

Buy from Tommy Bahama ($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.

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