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7 Resort Wear for Women Over 50

By Sandra Roussy August 11, 2023 Beauty

Are you preparing for your next vacation? Whether you’re jetting off to an exotic island retreat or savoring the serenity of a coastal escape, there’s one thing that should be at the top of your packing list: resort wear that is comfortable and that celebrates your personal style.

  1. Casual Beach Floral Maxi Dress from Amazon – Enjoy your resort in style with this lightweight and breathable beach dress featuring a flattering deep V-neck, adjustable spaghetti straps, side pockets, and a vibrant floral print.
  2.  ANNE COLE Plus Size Printed Crisscross Surplice Swimdress at Macy’s – Make a stylish splash with Anne Cole’s fabulous plus-size swimdress featuring a colorful print, trendy crisscross back, flattering surplice neckline, full bottom coverage, and lined design for comfort and confidence by the water.
  3. Echo Amalfi Maxi Dress Swim Cover-Up at Bloomingdale’s – This chic V-neck cover-up dress features short sleeves, contrasting details, and careful craftsmanship from India, effortlessly combining comfort and sophistication for a versatile and fashionable addition to your resort outfits.
  4. Pure Jill Washed-Linen Patch-Pocket Top – Indulge in ultimate comfort with this airy linen top, featuring a washed texture for added softness. This top offers an oversized fit, dolman sleeves, and an elliptical hemline that creates a beautiful drape.
  5. Travelers Floral Print Crops from Chico’s – Chico’s beloved Travelers™ Floral Print Crops are a customer favorite, thanks to their wrinkle-resistant sustainable fabric, gorgeous prints, and classic fit.
  6. Everyday Large Neoprene Tote – Simplify your everyday life with this convenient tote duo that makes the perfect companion for a weekend getaway, allowing you to effortlessly keep all your essentials in one place and enjoy a stress-free journey.
  7. Tencel Side Button Maxi Shirt Dress from Chico’s – Effortlessly chic and crafted from super soft Tencel, this relaxed-fit maxi shirt dress features roll-cuff sleeves, trendy side seam buttons, and a concealed button front.

From chic cover-ups that effortlessly transition from beachside lounging to poolside cocktails, to breezy maxi dresses that capture the essence of a tropical sunset, let’s take a look at trending resort wear for women over 50.

What Is Resort Wear

Resort wear refers to clothing and accessories specifically designed to be worn on vacation or at a resort. Resort wear typically embodies a relaxed, elegant, and comfortable aesthetic, perfect for leisurely activities in a warm climate, such as lounging by the pool, strolling on the beach, or enjoying outdoor dining.

How to Choose Resort Wear

Choosing resort wear involves considering your personal style, destination, activities, and climate. Here are some tips to help you select the right resort wear for your needs.

Consider the Destination

Take into account the location and its climate. Is it a tropical beach destination, a mountain resort, or a city with a warm climate? Understanding the environment will guide your clothing choices.

Determine the Activities

Consider the activities you plan to engage in during your vacation. Are you lounging by the pool, going for walks on the beach, exploring local attractions, or dining at upscale restaurants? Each activity may require different types of resort wear.

Prioritize Comfort

Opt for breathable fabrics like cotton, linen, or silk that will keep you cool in warm weather. Also, look for relaxed silhouettes that allow ease of movement.

Reflect Your Personal Style

Resort wear should be an expression of your personal style. Consider your preferences for colors, prints, and cuts. Choose pieces that make you feel confident and reflect your individuality.

Versatility Is Key

Select pieces that can be mixed and matched to create different outfits. This allows you to pack lighter and have more options. Choose clothing items that can be easily layered or accessorized to transition from daytime to evening.

Pay Attention to Coverage

Depending on your comfort level, consider the level of coverage you desire. If you prefer modest options, look for longer hemlines, sleeves, or lightweight cover-ups. Alternatively, if you enjoy showing more skin, opt for swimwear and dresses that suit your style.

Embrace Color and Prints

Resort wear often features vibrant colors and playful prints. Consider incorporating tropical motifs, floral patterns, or geometric designs that reflect the vacation spirit and add excitement to your outfits.

Pay Attention to Quality

Choose resort wear made from quality fabrics and well-constructed garments. Look for durable materials that will withstand travel and frequent wear, ensuring your clothing remains in good condition throughout your vacation.

Try Before You Pack

If possible, try on your resort wear outfits before packing them. Ensure they fit well, are comfortable, and make you feel confident. This will help you avoid any last-minute surprises or fashion mishaps during your vacation.

Remember, resort wear should reflect your personal style, provide comfort, and cater to the specific demands of your destination and activities. By considering these factors, you can choose resort wear that allows you to look and feel your best while enjoying your vacation.

Resort Wear Clothing for Women Over 50

Here are my favourite items of resort wear:

Casual Beach Floral Maxi Dress from Amazon

Casual Beach Floral Maxi Dress from Amazon

Made from a stretchy, lightweight fabric, this pretty floral beach dress offers unbeatable comfort and breathability. Its features include a flattering deep V-neck, adjustable spaghetti straps, convenient side pockets, and a wrap waist.

The floor-length design and vibrant trendy floral print make it perfect for any occasion. Pair it with your favorite accessories, sandals, and a hat to complete your resort look.

ANNE COLE Plus Size Printed Crisscross Surplice Swimdress at Macy’s

ANNE COLE Plus Size Printed Crisscross Surplice Swimdress at Macy’s

Prepare to make a splash with Anne Cole’s fabulous plus-size swimdress that will have you swimming in compliments. This swimdress features a colorful print and a trendy crisscross back, adding a touch of sophistication to your beach or poolside look.

The imported design boasts a surplice neckline, offering a flattering fit while ensuring full bottom coverage for comfort and confidence. The skirted bottom adds a feminine touch, and the dress is lined for enhanced support and comfort.

Echo Amalfi Maxi Dress Swim Cover-Up at Bloomingdale’s

Echo Amalfi Maxi Dress Swim Cover-Up at Bloomingdale’s

Enhance your beach or poolside style with this chic V-neck cover-up dress. Its pullover style offers convenience, while the short sleeves provide a touch of coverage and sun protection.

The dress is adorned with contrasting details, adding a stylish flair. Carefully crafted in India, it showcases the artistry and attention to detail.

This versatile and fashionable cover-up maxi dress effortlessly combines comfort and sophistication, making it an essential addition to your wardrobe. Whether you’re lounging by the water or exploring a coastal town, this cover-up dress perfectly complements your sense of style.

Pure Jill Washed-Linen Patch-Pocket Top

Pure Jill Washed-Linen Patch-Pocket Top

Experience ultimate comfort in this airy linen easy top, designed with a washed texture for added softness and a lightweight feel. The oversized fit, dolman sleeves, and elliptical hemline create a beautiful drape for enhanced comfort.

Complete with a scoop neckline, this top is crafted from 100% linen woven fabric and can be easily cared for with machine washing. With a low-hip length and 3/4 sleeves, it’s the perfect blend of style and retreat wear comfort.

Travelers Floral Print Crops from Chico’s

Travelers Floral Print Crops from Chico’s

Discover the beloved Travelers™ Floral Print Crops, adored by Chico’s customers for their wrinkle-resistant sustainable fabric and stunning prints. Crafted from travel-friendly and eco-conscious naia sustainable fabric, they feature a classic fit, pull-on style, and crop length.

These crops boast a comfortable straight-leg silhouette that remains clean-lined and wrinkle-free, ensuring you look flawless wherever you go.

Everyday Large Neoprene Tote from Tommy Bahama

Everyday Large Neoprene Tote from Tommy Bahama

Whether you’re heading out for a weekend getaway or to the beach, this spacious tote duo is the perfect companion to keep all your essentials neatly organized in one place.

With its generous size and smartly designed compartments, you’ll have ample room to store your belongings, from your wallet and keys to your phone, tablet, and even a change of clothes. Its sturdy construction ensures that it can handle the weight of your items without compromising its sleek and polished appearance.

Tencel Side Button Maxi Shirt Dress from Chico’s

Tencel Side Button Maxi Shirt Dress from Chico’s

This effortlessly chic maxi shirt dress is crafted with super soft Tencel and designed in a relaxed fit, complete with roll-cuff sleeves and trendy buttons along the side seam.

Pair this versatile dress with gladiator sandals for the ultimate go-to retreat look. The dress has a concealed button front, ensuring both comfort and style for any occasion.


Let’s Have a Conversation:

Are you going to a retreat soon? What will you bring? What is your go-to look when going to a retreat? Tell us about it in the comments below.

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The Author

Sandra is the middle-aged woman you hear about who sheds everything she owns and sets out into the world to rediscover and redefine herself. After more than twenty years spent in the fashion industry designing collections for brands such as La Senza, Victoria’s Secret, and JACOB Lingerie, she shifted her path and pursued her longtime passion for writing, traveling, and photography. Sandra was published in the NY Times best selling book Eat Pray Love Made Me Do It. A deeply personal essay hand-picked by Elizabeth Gilbert about loss, facing fears, and going after dreams. Visit her website:

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