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How to Rock an Over 50 Travel Wardrobe-Hawaii

Today I am joining my pals Sarah and Kim for our monthly Signature Style Edit.  This month we are talking about travel attire. I have been meaning to do a post on what I packed for our recent Hawaii trip so here we go.  I originally penned this post about this time last year before our Hawaiian trip got canceled and we went to Florida instead. This trip was a five-day trip to Hawaii for a wedding. Let’s talk about my  How to Rock an Over 50 Travel Wardrobe-Hawaii

Your best bet is to plan a capsule wardrobe of items that can be mixed, matched, and repeated.  I stuck with a neutral color scheme, for simplicity, to get the maximum wear out of the items I took. Linen and lightweight cotton were my staples.



Here is my packing list.


This is what I wore traveling to and from Hawaii.  These BR pants are great for traveling.  Here I am wearing them with flip flops, but I wore my Ilse Jacobson Tulip Shoes, which are also great for Summer travel.


over 50 style blogger cindy hattersley in banana republic pants and Michael Stars tee

Travel Days Cindy Hattersley

I took this J Crew Voile skirt that I purchased last year (it’s now on sale). It performed double duty as a coverup and casual skirt. Here I am wearing it with the J Crew swimsuit and with a linen shirt tied at the waist. I wore it as a coverup and for a casual lunch at the hotel

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

Here is how I utilized the capsule. The Etsy straw tote packs flat and expands to a large tote.  All items are linked below the graphic.

beach day hawaii trip cindy hattersley

The skirt could also be worn for a casual dinner, with the J Crew linen shirt tucked in with a jute belt from J Crew Factory  , and simple accessories and sandals. Grab the Mer Sea linen wrap in case it gets chilly. Sorry the picture is terrible.  I own it and love it!

Dinner Hawaii packing list


The skirt could also be worn again if necessary for a shopping day in town with a simple sleeveless tee from banana republic, reefs , the etsy tote, and simple accessories from etsy.

over 50 fashion shopping day


Another easy  item to pack and wear dress is this t-shirt dress from Target.  You can read my entire post on this dress,  How to Style one LBD Five Unexpected Ways here.

Here I am wearing it with sneakers which I did not take on this trip, but it would work just as great with flip flops or the Ilse Jacobson Tulip shoes.

cindy hattersley in target lbd, white hat, tennis shoes, and white jean jacket


This T shirt dress can be dressed down or up. It could be paired with the Ilse Jacobson sneaks (which can be washed by the way) for a morning walk, along with the Mer Sea Catalina Sweater which I love.  It is great for the airplane as well.

morning walk outfit Hawaii cindy hattersley


Or dressed up a bit for a lunch out.

lunch hawaii outfit cindy hattersley


The Michael Stars Gauze pant in black and white will be comfortable staples on this trip.  They can be mixed and matched with other items, they don’t wrinkle, and they could be easily hand washed if need be. Only packable hats are practical for travel.

Day 3 Island Exploring cindy hattersley

Here is the outfit I wore to the wedding. My favorite Lily Skirt with a linen shirt tied at the waist.  The earrings are no longer available unfortunately.  I know many of you have already purchased them.  The sandals are from laidback london here. They are fun with jeans too. You can purchase the lily skirt from CP Shades here.  I have it in several colors and I think it is worth every penny.  It is all about the cut.  I am eyeing the gray one (wish they would send it to me!)

Fashion Over 50 Beach Wedding

Here is the same skirt dressed down a little bit with my favorite Michael Stars tee. 

dinner out lily skirt cindy hattersley

Here I am wearing the white lily skirt with the black version of this tee.  I wore it to a wine event.



This packing list could easily be extended to a ten-day vacation with a few hand washings.  Gauze does not need to be ironed, and even linen looks fine with out ironing if you know how to air dry it. You might also enjoy my european version of this post here how to rock an over 50 travel wardrobe Italy.


Thanks for reading How to Rock an Over 50 Travel Wardrobe-Hawaii. Now let’s pop over and visit my Sarah and Kim.  I know they will have some fabulous ideas.









Reader Interactions


  1. I says

    I love all your luxe! I especially like the white blouse you wore with the black skirt… where is that from? I pack for a living for work, but on vacation I just can’t seem to pack lite enough! Once again great post loved everything

    • Cindy Hattersley says

      Hi Martha

      That linen shirt is from CP shades a few years back. It is different than their current romy shirt it is more oversized which I like. You can wear it out almost as a tunic, or tie it at the waist and it is long enough. I have three of them. Maybe they will bring it back or check on Ebay!!

  2. Joan says

    I haven’t been able to find a link to the black crossbody you used for your travel to Hawaii and can’t make out the name on the bag. Can you send it to me?

    • Cindy Hattersley says

      Hi Joan

      I emailed you. It is in the shop the post widget. You may have missed it.

  3. Barb L says

    Perfect timing! We’re going on vacation in a couple weeks. I devoured your last travel post, and used many of your great ideas/tips on a trip a couple months ago. Even bought the Amazon crossbody you recommended which I loved, and was perfect for traveling! You look so terrific in all these outfits!

  4. Elizabeth@pineconesandacorns says

    Cindy, I love your style and this post is chock full of fabulous ideas. I have pinned many for future reference.

    Off to check out Kim and Sahahs’ post.

    Have a wonderful weekend, I hope Summer is feeling better.

  5. Gray says

    Cindy A wonderful post! I think people love these travel attire posts. This one is really good – it shows you in the clothes too! I need to hire a photographer.

  6. Wren says

    Cindy’s recommendations are spot on. Linens and easy breezy cottons will be coolest. From personal experience of having a second home there, I learned to wear close-toed shoes on the plane (often cold leaving from CA) but I put a pair of flip flops in an outer pocket of my suitcase so I could put on more comfortable shoes when we landed and my feet instantly swelled in the heat and humidity, although my feet and body soon adjusted. Cindy’s shoe choices are wise. Go for open sandals of some kind.
    Lucky live aloha!

    • Cindy Hattersley says

      Hi Wren

      Thank you so much for the vote of confidence. I know you know! So fun getting together!! Let’s do it again soon!!

  7. kim says

    Cindy what a great post! I knew you’d kill it with your beautiful things. The combo of shirts and skirts and lovely basics with your accessories seems made for travel and packing! What a brilliant tote too. I always want to bring one and it’s not necessarily fun on the plane to use it as your bag.. The hats are perfect . I need to get so many of these things. I wish I looked as good as you in the CP Shades skirts. You should be their spokesmodel. I just LOVE that photo of you seated with kitty,. Also the tennis shoes and black dress is a new look on you and I love it. I’m pinning it all. You’re going to be all set for Hawaii and these ideas will help a lot of women planning trips!

    • Cindy Hattersley says

      Hi Kim

      Thank you so much. Sorry about the technical issues. I had a new one for me! I can explain if it ever happens to you! I agree about CP Shades if only they would hire me ha ha!! We already went to Hawaii last month but waited to post with you ladies!

  8. Sarah London says

    Extremely sophisticated look for such a casual holiday. I love it 👏🏻👏🏻👏🏻 And that linen skirt is very tempting!

  9. holly says

    What a great selection to keep things simple. I am using a couple of your ideas for something “new” to wear to girlfriend Happy Hour this afternoon. Thanks to you and Gayle on the hangers too! Do you have the link for the black and white leather sandals? My cute little Roxy sandals I had for years just broke and the ones you featured are exactly what I m looking for! As always, thanks for the inspo!!!!

    • Cindy Hattersley says

      Hi Holly

      Have fun at the girlfriends happy hour! Can I come? I added the link to the sandals. FYI they are inexpensive and comfortable! A win win! Sorry I had major technical issues yesterday! Hopefully it is all fixed now!

      • holly says

        Thank you, Cindy! Bought the last pair of sandals! Can’t wait to see my red toenails peeking out!

  10. Char M says

    Hi Cindy, My first venture into your noteworthy blog, and it’s time to shop! Please help me locate links on Hawaii feature for both collapsible straw tote and animal-print sandal. So chic and different!! Love how you stuck to color palette and kept the look effortless. I envision re-creating every one of these looks.

    • Cindy Hattersley says

      Hi Char

      First of all welcome! We are so glad you are here. At the bottom of the post you will find a link that says SHOP THE LOOK HAWAII. ALL OF THE LINKS ARE THERE!

      • Amelia says

        Hi Cindy.
        Love your picks for this. However, I find no links anywhere. There is nothing at the bottom of the post. Help! And enjoy your trip to Hawaii.

        • Cindy Hattersley says

          Hi Amelia

          I had major technical issues yesterday. My post would not update! It is fixed now. I hope! Let me know if you have any more problems!

  11. cherie says

    Oh, whoops, I spoke to soon. I found the link. Unfortunately, they’re out of it in the color I want. I’ll keep a watch…. Have a most enjoyable time with your family!

  12. cherie says

    Please, please post the etsy link to the flat bag that opens into a tote! I love it!!!

  13. home before dark says

    You’re gonna’ look cool and be cool. After the year you two have had, you deserve a great vacay!

    • Cindy Hattersley says

      Hi Patricia

      It has been a busy year! Looking forward to some small getaways and Hawaii!!

  14. Cheryl P says

    just ordered the straw tote! Great for going to the beach, shopping, etc! Have a wonderful time in Hawaii with your family!

    • Cindy Hattersley says

      Hi Francesca

      We won’t be travelling until September but we sure are looking forward to it.

  15. Roberta says

    I love your style and brands that appear in your blog. Have ordered several items and
    loved them all. Just reorganized my closet with Joy Magnano hangers. Got 50% more
    space. Is there a link to the sunglasses featured? Heading on a road trip up the Oregon
    coast. Need to get out of the heat in Southern Oregon.

    • Cindy Hattersley says

      Hi Roberta

      I added the sunglasses. Have a wonderful time on the Oregan Coast!

  16. Karen B. says

    Hi Cindy,
    You and your husband deserve a lovely vacation. You will look amazing in your selection of vacation wear. Have a wonderful trip.

  17. Juliet says

    Cindy … you’ll be the most stylish woman on the islands! Making note of your wardrobe list … I could use packable hats. After not traveling for over a year this topic is so timely … I think I forgot how to pack. You ladies have me motivated to start googling Hawaii flights. You’re going to have an amazing trip! xo

  18. Mary from Life at Bella Terra says

    Cindy, I have been traveling SO much that I feel like I should leave a suitcase packed all the time. Great reminder about what one needs for a beach vacation. Unfortunately my travel has been less fun and more business, but great post!

  19. Cindy Hattersley says

    Hi Gayle

    I need to try those hangers. I have so many things that slip off! I love your suggestion about washing linen. I am going to try your strategy!! That is why I love linen so much!

    • Gayle Miller says

      The hangers are the best! No bumps on knits, no sliding off the hangers, lightweight and indestructible. I only buy Joy’s brand. Imitations are worthless, IMO. Available from HSN and probably Amazon and eBay. Joy sold the brand to HSN, so no longer at Target. Bummer. The add on waterfall hooks are handy, too. I don’t think you’ll be disappointed.

      • Gayle Miller says

        I forgot to say that I only use this shower method for wovens. Knits would probably stretch too much. They should be rolled in a towel and dried flat. Most hotels have dryers, too.

        • Cindy Hattersley says

          Hi Gayle

          Thank you so much for sharing. I don’t iron any of my linen anymore. I hang dry and stretch!!

  20. GAYLE Miller says

    Cindy, I like to pack two or three Joy Magnano hangers when I travel. Hotel hangers don’t always make me happy. Re: hand washing, I generally take my favorite silk/ cotton tunic to the beach. It is dressy enough for most Florida restaurants, and cool enough to wear on the beach. I take it to the shower with me on Joy’s hanger, rinse under the shower and use a little shampoo on the collar and underarms. Rinse again and leave in the shower to dry. It is so lightweight it will dry very quickly. Ditto for the linen pants. Rinse, shampoo, rinse and hang by the hems. No ironing required!

  21. Mary Ann Pickett says

    I bought my sister these from your blog Ilse Jacobson sneaks and she loves them! You are going to have so much fun!!! YOU deserve it. I want that straw bag!!! Wish I could get it in time!

    • Cindy Hattersley says

      I think that straw bag is a winner, but I have not received mine yet. Love that it collapses for packing!

  22. LA CONTESSA says


    • Cindy Hattersley says

      Hi Elizabeth

      We will enjoy it. We have a few small trips planned before we head to Hawaii!

    • Carol S. says

      Looking for that tote link too. You’ll help sell a lot of those Cindy! Adore your style and packing list!

    • Cindy Hattersley says

      Hi Marilyn

      So sorry I always manage to miss a link or two. I fixed it and emailed you the link as well! It is a great tote!

      • Annie says

        Gorgeous, elegant and casual. Love the neutrals lifted by the wonderful accessories. Unfortunately I still cannot access the link to the fold flat tote. Is it possible to add it to the carousel at the end? Thank you for the post and the links.

        • Cindy Hattersley says

          Hi Annie

          I am sorry I had a technical issue yesterday. My post would not update!! I had to call in my amazing tech guy. I added the link to the carousel but here it is as well.[show_shopthepost_widget id="4799613"]

  23. Nancy O. says

    Packing now for a trip to Seattle to visit son, daughter-in-law, and 2 year old grandson. Haven’t seen them for almost 2 years. I’m beyond excited and am already packed…very casual clothes, 2 hats, sneakers, a comfortable cross-body bag, and a tee-shirt dress if we get out. Love your blog and instagram, you always have something that interests me.

    • Cindy Hattersley says

      Hi Nancy

      I am so happy for you! Have a wonderful time with that grandson. I know how hard it was when we could not see Summer. So happy we are all getting back to normal!

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