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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

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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

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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

lily-skirt-michael-stars-tee-and-summer-accessories

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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

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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

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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

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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

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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

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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

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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

NORTHERN CALIFORNIA STYLE

 

Reader Interactions

Comments

  1. Lori says

    Cindy, I love your style first of all. Could you tell me how you tied the white mersea linen wrap? Love that look with the wide leg pant.

  2. Téa says

    Hi Cindy – I’m new to Bryn Walker – thanks for the rec’s ! Here in the mid-Atlantic, the humid, schvitz-inducing weather begins around mid-April. I just can’t handle anything BUT linen and dresses. I love all these ideas!

  3. Ell says

    Love the Mersea linen wrap—is there a tutorial for the different ways you have styled it??

    • Cindy Hattersley says

      Hi Eli

      That wrap is so versatile in my humble opinion, you can tie it on the side, in the front, throw it over one shoulder…the possibilities are endless!

  4. Cath🇨🇦 says

    Having a coffee ☕️ watching YVR wake up from a 6th floor room at the Fairmont Airport .
    I love this hotel in Vancouver… fabulous views of the mountains and busy airport, and shortly the sunrise 🌅 , but so soundproof. Absolutely wonderful to fall into bed after arriving from
    St Lucia at 3:30 am 😵‍💫 Caribbean time . Best beds and luxurious pillows…and awards for top airport hotel in North America.
    Like you, Cindy, I embrace linens for the heat. Soon will take ferry home from week long PONANT cruise … Barbados to St Lucia with only 123 guests .👍. I took along sleeveless tops and one print tunic ( all White Stuff from UK) and coordinating pants ( L.L.BEAN years ago) , and a little spray bottle that I fill with water to ease out the wrinkles overnight. Smooth down wrinkles and hang up. Works so well! Learned that from a contributor recently…. sharing of ideas is so helpful. Linen is not for flight travel, but otherwise just the thing for tropical weather.
    I learned not to pack my colourful chunky ( heavier) necklaces due to weight , but couldn’t help just one! Really like seeing how you use your collection to advantage to accessorize your outfits.

    Although I am pretty pleased with my toning up from Reformer Pilates and eating more salads and soups pre holiday, I have always been aware of my less than gorgeous thighs… but I am a keen swimmer and also found opportunities to do my energetic deep water workout . May not be the best legs , but they sure work hard for me. If others don’t like the view, then avert your eyes!
    At almost 73, I have learned to enjoy my good health… and accept the road map of veins and cellulite … which I’ve had since my teens. 😬

    • Cath🇨🇦 says

      PS should mention that this was to be the Caribbean PONANT cruise in March 2020… we were actually in Martinique seeing our beautiful small ship in the bay on the 12th! 🦠😷 But… after three tries we finally were able to enjoy it , and so worth the wait.

    • Cindy Hattersley says

      Hi Cath

      I love that…if others don’t like the view…avert your eyes. I have lived that mantra my entire life due to my burns. Wise words…

  5. Barb L says

    You look so great in all your looks and your hats too! Love that jacket and of course your wraps. Of course I’m sitting here in fur lined slippers wrapped in a blanket, but spring is just around the corner. Thanks for all the inspiration!

    • Cindy Hattersley says

      Ha! It has been dark dreary and cold here too Barb! Very unusual for this tie of year!

  6. Liana says

    You look beautiful in all your resort wear in all honesty, I really don’t like summer clothes. I don’t wear sleeveless looks nor anything that shows leg skin and for swimming I’ve been wearing the same long sleeve scuba suit for the last 4 years. My husband says I look like a Muslim during summer and I don’t disagree. .

    • Cindy Hattersley says

      Ha! I do wear linen but almost everything has sleeves. Linen and light cotton do not need to be sleeveless to be cool, just loose!

  7. Juliet says

    Perfectly timed post, Cindy. You and Kim are offering up all kinds of ideas and inspiration for my upcoming trip to Mexico. It’s been a long long time since I’ve been on real vacation, I forget how its done. I’m loving the lightweight, flowing pants, skirts and dresses you’re sharing here. As for bathing suits, your attitude is great and I need to adopt it. Truth be told the reason I haven’t been on a sunny vacation is because I feel terrible about how I look in a suit. I know at my age I should be beyond it, but I’m not. And there is no suit in the world that addresses my biggest problem area, my legs.. Unless the 1920’s bath costume comes back in vogue. Sigh. Hope Steve progresses from the scooter soon, but no need for you too to jet off anywhere … you live in a resort paradise! xo

  8. Nancy says

    Oh, to be as stylish as you are! Wow! I love this post and all your looks. I’ve been catching up and checking out all of your other links from this post. Amazing. I’m curious if you’ve ever said how tall you are? If so I missed it.
    I’m 5’1″ (now), used to be 5’2″, and as much as I like your looks, those wide leg pants may not be something, as a petite, that I can pull off. Thanks Cindy!

    • Cindy Hattersley says

      Hi Nancy

      Aren’t you sweet! I am 5’4, but very long waisted. All my height is on the top! I always wear a “cropped” look so they aren’t so long on me. I think you could pull it off.

  9. Wren says

    Although not Hawaii or Mexico, I’m about to go someplace that will be very hot and humid so these looks are perfect timing. I’m waiting for a long linen tunic that I ordered but the Gap linen shirt looks great also at a much lower price. I’ve walked by Maison Marianne a million times but the fashions she has in her windows don’t attract me to go inside (sorry to sound offensive). The styles that you wear look great on you, I just don’t think things that unstructured aren’t for me. I do have that Tommy Bahama jacket in white and will be taking it on this trip for evenings in AC when I’m wearing sleeveless. Now if we could just get some warmer weather here on the Central Coast!

  10. La Contessa says

    BRYN Walker in SLO!
    How FABULOUS IS THAT!
    I WAS ON THEIR SITE THE OTHER DAY FOR THE NEW SPRING COLLECTION BITS!
    I can wear size medium to an extra large now!
    I adore their heavy linen which would be too hot for your area!
    That’s a really good photo of the two of us💕
    Xxx

    • Cindy Hattersley says

      Hello Eliz

      You are the one that turned me on to Bryn Walker. You would love Marianne’s little shop in SLO. She has great stuff. Yes that photo is a keeper!!

  11. kim says

    Cindy, You look so great in the Tommy jacket! Love this post and I especially adore the white skirt and dress and how you pull the wraps over things and make everything look chic! If people can just get your gorgeous basic pieces they really need nothing else to be comfy and stylish on holiday. So fun doing this. Now can we just get some sun?
    xo

    • Cindy Hattersley says

      Ha!! Sun we could use! Your post was packed with great tips and so many good pieces! I am all about the accessories. People probably think I am boring!!

      • Lori Schulte says

        I love this. Like the others asking, how tall are you? You look great in the wide leg look but I do not. , I just look frumpy in them. What is the height requirement to look good in either wide legged pants or long skirts? I wish I could pull it off as you look so cute in them. I’m tired of skinny style slacks, so could you do a post on some of your favorite non skinny style jeans? I find it so hard to find a straighter jean that is flattering (and non flared/bell boot leg, or skinny jean, or wide leg) that looks good on a slim 5’3” frame.

  12. Francesca B says

    Such a fantastic post thank you Cindy for all the looks and ideas. I bought that Tommy Bahama jacket last year after Kim’s suggestion and it is such a winner. We are going on a vacation this summer so l have so many ideas here to look at. I think l will have have to get those linen pants you fweature they look perfect! Happy weekend:)

    • Cindy Hattersley says

      Hi Francesca

      I kept eyeing that jqcket and was afraid it would be too short on me. When I saw Kim in it I knew I could wear it! Tempted to get it in other colors it is so great!!

  13. Lisa says

    Every time you mention the Lily skirt, I forget to ask what size you purchase. We are of similar build and they look fantastic on you. Here’s hoping I can pull it off, too!

    • Cindy Hattersley says

      Hi Lisa

      I replied but think it disappeared! I wear an XS. I can wear a small as well but I really prefer the XS.

  14. Karen says

    Cindy I’m so glad you found a swimsuit that you feel good in. Every woman of a certain age deserves to participate in life at the beach or pool! We shall NOT be sidelined to the margins while everyone else has all the fun!! La Blanca is also a good brand to look at, their one pieces and tankinis don’t sacrifice style for coverage.I believe they come in torso options too. Robin Piccone looks super cute too if you ever come across it. Love you and your amazing work here. K

    • Cindy Hattersley says

      Well hello Ms Karen!!

      I find those La Playa suits to be too high cut for me. Maybe I need to take another look because I love the look of them! I will take a look at Robin Piccone as well. You always look drop dead gorgeous!

  15. Gray says

    Love your linen looks – I am a fan too, but I don’t like how it wrinkles so badly.
    Enter CP Shades!! I plan to buy 2 skirts and 2 pants from them. The lightweight wrinkled look works for me. Thanks for another great post Cindy! You always look darling.

    • Cindy Hattersley says

      Hi Gray

      I love linen that is meant to be worn wrinkled. You would love those Aunti Oti shirts too!

  16. Kerry says

    I love how you make an outfit unique to your style and personality. When I see an ad or a design, I struggle to think outside the box. But, you have great style!

  17. Frances Longstaff says

    Really enjoy all of your posts! I have a question regarding the blouses that you are tying at the waist. Did you tuck in the back of the blouse or are you gathering the back up when you make the tie at the front?
    Thank you for all your posts!!

    • Cindy Hattersley says

      Hi Frances

      Great question! I just sort of roll it under in the back and then tie it in the front. I am glad you asked. I just do it sort of subconsciously! Thanks so much for reading!

  18. kim says

    Cindy I forgot to say I am crazy about all those Mango pieces! Some fab finds there right? My new go-to for cool things at good prices. xo

    • Cindy Hattersley says

      Hi Kim

      Yes! So far things fit too. I find Zara and some of the others are so undependable as far as fit goes. I am a big fan so far.

  19. kim says

    Cindy I love your post! It’s wonderful all your looks have the accessories and everything you need.. That last dress is so good both ways, but I love the strapless look on you. The Farm Rio pants are fun and modern. I love their things. Still, you really make me want the skirt and the leopard swimsuit.. very classic and chic! I knew you’d have a lot of beautiful things on your post and you have a gift with styling. I am loving the house pics too. It sure looks pretty and the front entrance has the Cindy vibe! Thank you for being so patient with me this was a crazy week, but I adore you both and feel honored to do this with you stylish gals. xo Kim

    • Cindy Hattersley says

      Hi Kim

      Your post was wonderful. You always have things I want! I need to call you about that linen jacket. I love it but am worried about the length with my long waist! I have been looking for something just like that! Thanks for joining Sarah and me. We love having you!

  20. Karen B. says

    You are such a great help with wardrobes and I find that I’m heartened to try some of the more adventuresome (for me) to try some of the fashion you’ve shared.
    Enjoy your vacation to Hawaii. You’ll be the most well-styled woman in the area.
    xo,
    Karen

    • Cindy Hattersley says

      Hi Karen

      Most of my life is spent in yoga pants but I sure am enjoying wearing decent clothes again!!

  21. Liana says

    You look fabulous on every picture and the outfits are just as beautiful. The Mango palazzos with lavender shirt . I’d never had though of that color combination, but it looks amazing , that’s real talent right there 😉.

    • Cindy Hattersley says

      Hi Liana

      I was told (by an expert) many years ago that I should wear more purple, which of course I never did. Once my hair was gray, I really learned to embrace lavender. It is hard to find most seasons, but this year I am seeing more of it. Those pants fit beautifully and feel expensive. I am very impressed with that brand so far.

  22. Mary from Life at Bella Terra says

    Cindy, you are just too funny! I don’t recall how tall you are but do the wide pants look good on someone shorter? Like 5’4″? They sure look comfortable but I don’t need anything that will make me look stout….if you know what I mean. You are funny about wearing a bathing suit, but I feel the same way. Having my last baby at 45 and my first at 39 (emergency C-section)…need I say more? I need to go shopping this week as we are headed to Nantucket soon….Thanks for sharing and thanks for the humor!

    • Cindy Hattersley says

      Hi Mary

      I am 5’4 exactly. I am long-waisted with short legs. All of the wide legs that I have shown are a perfect length except the black and white. They need to be hemmed. They are all so comfortable and freeing I have to tell you!!

  23. LA CONTESSA says

    EVERYTHING LOOKS GREAT!
    ESPECIALLY THAT LONG DRESS ON YOU TIED AT THE NECK!
    I DIDN’t see any BINGO ARMS!
    I’m seeing MORE COLOR IN YOUR WARDROBE!
    GOSH if you weren’t a size XS we could shop in each others closets!BUT ALAS I ‘m an extra large………
    HAWAII HERE YOU COME!

    • Cindy Hattersley says

      Hi Elizabeth

      I thought maybe I was pushing it with that long dress (the arms!!). I thought it would be great for Hawaii. I find if you wait to long to buy anything for late summer it is all gone, so this post was timely. I am channeling you…trying to add more color!

  24. Claudia Manginelli says

    You look stunning in all the outfits you modeled. Don’t be so hard on yourself. I admire how beautiful you are with all your “imperfections”.

    • Cindy Hattersley says

      Hi Claudia

      Thank you so much. I have learned to live with them all and embrace them at this age!!

  25. Judy says

    I love this post BUT, I went to order that darling leopard J Crew swim suit and it’s SOLD OUT. I’m so sad…it is just the cutest. I better get going on ordering a couple other things I love from your post. I suspect when you feature something on here, it doesn’t last long!

    • Cindy Hattersley says

      Hi Judy

      I can’t believe that darn suit sold out! I have been told that it can happen. I once featured something from Madewell (can’t remember what it was). When I walked into the Walnut Creek store the clerk said apparently some blogger featured this and it is sold out. Those shoes from my Sunday post just went immediately. I try not to feature anything unless they have plenty of stock, but sometimes it happens. Keep checking back, I think inventory is very unpredictable these days.

  26. Heidi says

    Hi Cindy,
    Nice! Everything looks really fun and light for the heat. I wish I had an upcoming tropical vacation to plan and shop for!
    Those wide legged pants from Mango are great, sadly out of stock in my size. Oh well. I really don’t need any more of anything.
    If it ever warms up here I will start wearing my skirts and linen. Still too blustery and cool.
    XO Heidi

    • Cindy Hattersley says

      Hi Heidi

      Hasn’t this been the coolest Spring and early Summer in recent memory? We had better weather at our old house so it is harder for me to compare, but it wasn’t warm there either! Looking forward to seeing you soon. I love coming to your area. Call or email, I am getting settled and could meet for lunch anytime!!

  27. Sarah says

    Cindy, you’re my hero. I had to LOL when I read about flexing your “bingo arms” for photos. Thank you for being honest, for being human, and for inspiring us “old dogs” to try some new tricks. You look fabulous, and you make me want to try to do the same.

    • Cindy Hattersley says

      Hi Sarah

      We old dogs have to try new tricks, don’t we? These years are the best of our lives, we need to celebrate them!!

  28. Wren says

    I jumped off from reading you to order the pants from Mango, before I even finished your post. Hope they fit!
    Ironically, I’m in the Kona airport waiting to fly to SJ. Our lifestyle means a lot of Hawaii and Mexico so I need clothes for that life. I’ve recently given away a lot of my island wear that I deemed too young for me. You offer encouragement for the halter style-I just decided against a dress while here since it was that style. It was SO gorgeous. I may still try to order.
    Thanks for some fun fashions. I think we all have to cut loose with that kind of clothing sometimes and you will look smashing on your trip Im sure. Aloha!

    • Cindy Hattersley says

      Hi Wren

      I know exactly what you are talking about. When Sarah and Kim said resort wear I thought eeeek! Sometimes we have to think outside of the box. It is challenging but we can. Like the good ole Target dress. I still get compliments on that thing every time I wear it. I think the higher neck and the cutaway sleeves, or tie-neck are the trick. They draw your eye up. I am no expert. I have just found through trial and error I can make that work occassionally!

      • Wren says

        In regard to Mango, if I remember correctly, they have children’s clothing too. I came across a store in a big airport shopping area (Heathrow?) that I think was Mango and they had darling clothes, just for kids. I bought something for my grandson and it’s a thought for your Summer.
        P.s. Saw the 2 places for fountains today on the drive home from SJ airport. Will have to investigate when I visit my daughter in Morgan Hill next time. Thanks for the suggestions.

  29. RacheLle says

    You are so stylish. Love everything you demonstrate. Always looking forward to seeing the decor and fashion. I thank you for that 🥰

    • Cindy Hattersley says

      Hi RacheLle

      Thank you so much. I am so glad you enjoy the blog. I certainly enjoy each and every one of you.

  30. Nan says

    You are your grand daughter Summer’s twin in the lavender linen shirt and paisley pant! Looking great in all outfits, Cindy!

    • Cindy Hattersley says

      Hi Nan

      Do you think so? Poor thing!! She still thinks I am pretty cool. Wait till she gets older and somebody tells her that!!

      • Nan says

        Trust me- Summer will always think you are cool and beautiful! Grandmother and granddaughter relationships are special. Mine was the kindest, most elegant woman! At any age, I loved hearing how much I resembled her and inherited her style sense.

  31. Carol says

    Please send nothing back because you look fantastic in all of it. Mango is new to me but I will checking that website.

    • Cindy Hattersley says

      Hi Carol

      I am a new fan of Mango. I have yet to get to a store. I honestly didn’t have a clue who or what they were. I know everyone likes a good price point and I like to feature things when I can. So far they get high marks from me, for quality and fit for the price point.

  32. Mary Ann Pickett says

    OMG…DARLING. Everything!! I’ve had my eye on those Farm Rio pants but worried that hemming up would cut off some of the design. I love all the happy colors. Going to have to do some pinning here and shopping 🙂

    • Cindy Hattersley says

      Hi Mary Ann

      Well of course you would look darling in those pants. I think they would be fine hemmed up. They would be great for Spain!

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