Best Resort Wear for Women Over 50

I am so happy to be joining my friend Kim from Northern California Style for our monthly Signature Style Series. This month we are talking about women’s resort wear. I originally penned this post with both Kim and Sarah two years ago, since you were still reading it, it was time for an overhaul with all new information and pictures.

We personally will not be jetting off on a resort vacation until Steve is off his scooter. Here in the Paso Robles Wine Country it gets quite hot in the Summer so casual resort wear is perfect. Let’s chat about the Best Resort Wear for Women Over 50.

If I were heading to a beach vacation like Mexico or Hawaii , I would be wearing comfortable pieces of casual linen and cotton, with sandals, flip flops, and sneakers. That same vacation wardrobe is pretty much my uniform here in the Summer as well. I rarely wear denim or synthetic fabrics in the summer when it is hot. If I were traveling, I would keep my color palette simple so I could mix and match things and fit them in a carry on suitcase. You can read about what how I did that, in my post How to Rock an Over 50 Travel Wardrobe Hawaii. Since I am not traveling, I have added a little color for fun.

I love these new to me (Auntie Oti) light as a feather shirts. I purchased mine at Maison Marianne in San Luis. She has a lot of pretty colors right now and can order in any that she doesn’t. If you are local pop in and visit Marianne. She is delightful to deal with. You can also order from her website. You could also easily substiture a gauze or linen shirt as well. The linen pants are from Bryn Walker. Marianne also carries these. All available items are linked below the post.

Cindy Hattersley in Bryn Walker and Autnie Ot-resort wear women over 50


This purple shirt is also from Auntie Oti. I love these shirts because they are super light weight and they cover the arms!! The pants are my favorite style from Bryn Walker. I wear and XS in Bryn Walker. The jacket is from Tommy Bahama. Kim inspired me to buy it. It has the casual style of a jean jacket but is lightweight linen. It comes in many other pretty colors as well. I am wearing a medium. For fun I added my Artemis Design Co slippers, but if I were traveling I would probably wear a neutral shoe that would go with everything.

Over 50 Style Blogger Cindy Hattersley-resort wear women over 50


I am a big fan of CP Shades and their Lily Skirt in particular. It is really pricey, but the design is very flattering and can be dressed up or down. I find them to be really cool in hot weather. I would never travel anywhere hot without one. I am wearing it with my favorite Michael Stars tee and simple bamboo jewelry. I have linked a more reasonable alternative at the bottom of the post and a few that have popped up on eBay. I hate to admit how many lily skirts I have. You can see them styled in my popular post How to Style Black and White in Summer, Skirts you can wear now or Later, or Five Tips on How to Transition Linen Apparel into Fall



In this photo I am wearing linen wide leg pants no longer availabele, the mersea wrap, inexpensive earrings, a pricey but worth it Helen Kaminski hat, and reasonable Dolce Vita Sandals. When you wear a flowing skirt or pants, a hat like this compliments the look. Bag is from Etsy.

cindy hattersley wearing nicole-paloma,-linen-wrap,-helen-kaminski hat


Here I am wearing my favorite Michael Stars tee, Bryn Walker pants, Tommy Bahama jacket, Helen Kaminski hat and Mia Sandals.

over 50 style blogger cindy hattersley in tommy bahama jacket & bryn walker pants helen kaminski hat


This look is very simple Bryn Walker pants in black and Michael Stars as well. I topped it with the Mer Sea Wrap in Gray. Can you tell I love linen? Pretty earrings from a favorite Native American artist and dolce vita sandals.

over 50 style blogger Cindy Hattersley Cindy Hattersley in Bryn Walker linen and Mer Sea


You can get a lot of mileage out of a great white dress. This white dress from Hannoh Wessel I purchased on sale at a local favorite boutique Andbe. It is no longer available but I have linked another dress that is very similar. I don’t normally wear sleeveless, but If I wear it with the Mer Sea linen wrap it is quite cool in hot weather. I wore this dress all the time last summer. The great thing about a wrap is you can tie it different ways and you have a completely different look.

over 50 style blogger cindy hattersley in hannoh wessel dress and target wrap


Here I am wearing it with the white Mer Sea Wrap at Kim’s birthday last year. You may recognize my pal on the left The Contessa!! Here I tied the Mer Sea wrap to one side.

Cindy-Hattersley-and-Elizabeth-(the-Contessa)-hannoh wessel dress

If the weather is cool you can style it with a topper. This one is from Maison Marianne in San Luis Obispo as well. It is no longer available, but Marianne could help you with this year’s version. I have shared similar below the pic. The necklace is by Paula Carvalho

over 50 style blogger cindy hattersley in black and white duster hannoh wessel dress


I love these two fun pieces from Alembika. The Garden Lantern Pants, and the Clea Cutaway Top are super comfortable, lightweight, and just plain fun. You can shop both pieces right here, and get 20% off with the code CINDY20. How fun is that?

Alembika Garden Lantern Pants and Clea Cutaway Top-cindy hattersley

Alembika Garden Lantern Pants and Michael Stars Tee cindy hattersley

Last but not least…What should a 60 year old woman wear to the beach? My answer is simple, whatever you feel comfortable in. You will not catch me modeling swimwear here, use your imagination on that one. I know we should be proud of our bodies at this age and all but, as I explained in my interview with 365 days 365 women I was badly burned as a child, I have had two hip replacements, and I have the usual aging issues that we all do. I will wear one, I am not going to miss out on the fun, but it isn’t pretty!! My favorite suit is the maldives tankini from Athleta. I have several. It has a high neckline with good coverage. Generally, tankinis work best for me because I have a long torso. Most swimsuits (unless I purchase a tall) don’t fit me properly. I am a big Athleta fan as you know and the Maldeves tankini also comes in bra sizing which is another plus. I also plan to purchase a rash guard and a swim skirt for extra sun protection this year. Don’t forget your sunscreen.

This picture is from two years ago, but I still have the bathing suit from J Crew and the cover-up. The skirt is from J Crew is no longer available, but I have linked very similar below and a few from eBay. The one-piece swimsuit is still available. I ordered the suit in a long torso. I hate having a suit creep up my “booty” as Summer says. I think you could wear it as a coverup by day and with a linen shirtby night like I did here. It is light as a feather, perfect for a coverup. I am wearing it with an older Helen Kaminski hat which I have linked below as well. FYI Helen Kaminski hats are pricey but worth every penny. I have had this hat (a gift from a dear friend) for at least 15 years and it still looks like new.

cindy hattersley in j crew skirt & suit & cp shades shirt


You might also get more inspiration from my post How to Look Stylish in all White after 50, or my recent post on the Eileen Fisher Terry Separates How to Make Sweatpants Look Chic over 50. They would be great for traveling as well.

I prefer to keep my accessoriesto a minimum in Summer. I usually wear either bone, wood, or raffia, or a couple lightweight Native American pieces. I hope you enjoyed Best Resort Wearfor Women over 50. What will you be packing on your next vacation? Now let’s pop over and see what my friend Kim, is sharing. I love her style. You can also follow Kim on Instagram here.


Best Resort Wear for Women Over 50

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