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Best Comfortable and Chic Travel Outfits for Women Over 50

I want my travel clothes to be stylish, but I also like to pack pieces that I can wear multiple ways many times to create different looks . Travel outfits in my opinion should be as wrinkle resistant as possible with the ability to layer. Let’s talk about the Best Comfortable and Chic Travel Outfits for Women Over 50.

What to Pack

If you take a few black and white pieces, add your favorite pop of color, and fun accessories you can easily create a travel wardrobe that fits in a carry on for a five-seven day trip. I would shoot for taking two pairs of shoes and maybe a pair of sandals or flip flops depending on the time of year. Sneakers apparently are “de rigueur” with everything these days. I have linked all available items or similar at the bottom of the post.

COMFORTABLE CHIC TRAVEL OUTFITS OVER 50

I would take the five organic terry pieces that I featured in my post How to Make Sweatpants Look Chic Over 50 and add two key pieces from Alembika, the Kylie Jacket and their Iconic Stretch Jeans. You can use the code CINDY20 for 20% off.

Alembika sent me this great Kylie jacket and I am in love! I am wearing it with their iconic stretch jeans, gelato sneakers, (I buy mine locally at shoe tree Paso Robles) michael stars tee ,and an older MJ Wallace bag. This jacket is wrinkle resistant and could be styled numerous ways. I would wear this on my travel days without jewelry so you can clear airport security easily.

cindy hattersley in travel friendly Alembika Jacket & Pants

The Kylie jacket is great for layering. You could also add a scarf or a cashmere wrap for extra warmth on the plane. It could also be worn as a dress during your stay with sneakers or dressed up with a pair of flats.

When Alembika suggested these iconic stretch jeans I wasn’t sure about them. She said they are one of our best sellers. Yael the owner designer said I think you will love them. She was right. The fabric is flattering, forgiving, and comfy. They have enough weight to keep you warm on the plane but are lightweight enough to be worn like this on a warmer day.

I am wearing my favorite Michael Stars t-shirt in white here with the iconic jeans. I like this Michaels Stars tee because it has 3/4 sleeves, a much more flattering length for women my age.

Alembika Iconic Stretch Jean-travel outfit-cindy hattersley

Here I styled the Kylie jacket with a red Michaels Stars tee and the Eileen Fisher organic cotton terry crops that I love. The huge pockets are big enough to hold an ipad! I normally try to wear the same thing going and coming when traveling. I would wear which ever pair of pants were less for the wear!

Alembika Jacket, Eileen Fisher pants-cindy hattersley

All of these Eileen Fisher french terry items (except for the long jacket below) are on sale so now is a good time to pick them up. I know many of you have and love them. If our weather was more normal for this time of year, I would be living in these pieces.

cindy hattersley in Eileen Fisher terry

Here I am wearing the Eileen Fisher Organic Terry Pants & Sweatshirt with a linen scarf. You could easily add a lightweight cotton or Cashmere shawl as well .

cindy hattersley wearing eileen fisher black terry and a linen scarf

My friend Wren featured here on Ageless Style, turned me on to these Olukai sneakers. She said she wore them all over Europe. They are great for Summer because they are perforated and the backs can also be worn down if you are prone to blisters.

cindy hattersley in eileen fisher french terry

Here is an example of how you can “dress up” sweats. If I were on a 5 day trip I would probably not bring these leopard mules although they don’t take up much space. I would replace them with a pair of birdies that could be worn with the Alembika Kylie jacket as a dress for dinner out. This fun horn jewelry is lightweight and takes up little space. My pair of sunglasses are from Specs by Kyla in Atascadero. from Alba Optics. These are super lightweight and would be great for travel.

cindy hattersley in eileen fisher french terry

I have really become fond of the crossbody/ waist bag. Although I never carry them on my waist. I have the Athleta Excursion bag in black and I carry it nearly everyday. It is big enough for a small bottle of water, sun glasses and wallet. It also comes in pink and white if black is too boring for you. This price-friendly old navy sweatshirt and amazon sweatpants could be substituted for the Eileen Fisher if price is a concern. The amazon pants have good reviews and the old navy sweatshirt is a favorite of mine. You can tuck in a pair of yoga pants or leggings easily as well for hiking, workouts and walks.

Cindy Hattersley in Athleta Red Leggings and Sling

SHOP THE POST

If you are packing for a five-seven day trip the key is to keep your travel capsule wardrobe simple, so it will all fit in your luggage. A neutral color scheme is best. I added in a pop of color for fun. I kept the jewelry and accessories simple. If you were traveling on a business trip you would need to substitute some skirts or dresses or a blazer. A swimsuit could be added if there will be a pool. This trip is meant to be a short casual trip so keep the packing list simple. You can always add a sweater or two, and scarves take up very little space.

Thank you for reading the Best Comfortable and Chic Travel Outfits for Women Over 50. What are your best traveling outfits? Do you have some go to items that you consider your best travel clothes? Are both style and comfort important to you when traveling on vacations? Let’s get this conversation going.

EDITORS NOTE:

USE CODE CINDY20 to receive 20% off anything at Alembika

MICHAEL STARS IS HAVING 20% OFF ALL OF THEIR TEES

SOME OF THE EILEEN FISHER ITEMS ARE ON SALE AS WELL

Reader Interactions

Comments

  1. Patti says

    Just a note to readers that I held my breath and ordered the VERY expensive Frank & Eileen Carmel Travel Set and was so disappointed. I travel a great deal but I hesitate even leaving the house in this it looks so unflattering. No shape to the top whatsoever. Bottoms too wide at the bottom even for flare. Over $400 for this?

    • Cindy Hattersley says

      Hi Patti

      Thank you so much for sharing. I hope you did not think I recommended that? It is very similar to the Eileen Fisher that I did recommend and am very happy with. I wear them all the time.

  2. NCSue says

    Super choices Cindy! You have such style!!! and your hair is gorgeous…I am jealous.
    What size do you wear in the EF crops?

  3. Bonita Gillespie says

    Love , love , it all. You cannot go wrong with the red accents. We just returned from. Vacation so will keep your post in mind for my next trip. . Love your posts!

  4. Annie Diamond says

    Cindy,
    Every look is perfect! I love the Amelbika long jacket! It looks so good with the black pants and red sneakers! You have the best style Cindy!

    • Cindy Hattersley says

      Hi Annie

      Thank you! That Alembika dress is cut to flatter, and it is very comfortable. You need that dress! It spells Annie!

    • Cindy Hattersley says

      Hi Colleen

      I absolutely adore those pieces! If our weather would warm up just a tad…I will be living in them!

  5. Barb L says

    Love everything about this, and you look great in each outfit! You show so much versatility and I’ve saved this to use as a reference for future travel! (Wow – love that Kylie jacket) Hope you’re staying safe (and dry) with all the rain.

    • Cindy Hattersley says

      Hi Barb

      Isn’t that Kylie jacket wonderful? I had a similar jacket from Artful Home that I must have left somewhere. This is a great replacement!

    • Cindy Hattersley says

      Hi Mary Ann

      Thank you so much! That jacket is fabulous. I will be taking it with me on my travels!

  6. Karen B. says

    Cindy,
    I would wear each of these outfits even if I was only going to a friend’s house. You have such great style and I always leave with new ideas for my own wardrobe.
    Karen B.

    • Cindy Hattersley says

      Hi Karen

      I am so happy to hear that KB! You are the best. I so appreciate you!

  7. Gray says

    Love this post Cindy – I have never been able to pack successfully with a capsule. Every time I see one of these posts, I think “maybe next time”. I am usually traveling with Chip on business, so we have to pack for pool/beach, sightseeing, hiking/jogging/biking and then dinners at night! Whew. If I won the lottery, I would hire a cook and a packer….🤣

    • Cindy Hattersley says

      Hi Gray

      The other issue is how unpredictable the weather can be. We traveled to Italy the year it snowed and was freezing cold. I packed a pair of flip flops for the shower etc., and ended up wearing them the entire time. I never wore my boots once!

      • Gray says

        I hear you! My weather app was completely wrong for Hawaii in January and for Charleston in March!

  8. eileen chadwick says

    Cindy Love your new haircut…you found the right hairdresser ! Color , shine and movement!!

    • Cindy Hattersley says

      Hi Eileen

      Thank you, yes Edward Tedeschi is really good. I highly recommend him. Anyone unhappy with their stylist that is coming to the area might benefit from scheduling an appointment with him and have your hairdresser try and copy the cut.

  9. Ginger says

    Love all of your black and white outfits with pops of red! I’m interested in the Michael Stars tee, but not sure if sizing… What size do you wear?

    • Cindy Hattersley says

      Hi Ginger

      I wear a small but think a medium would work as well. I have never shed the covid pounds unfortunately. I need to get back to weight watchers!

  10. Leslie Toms says

    Fabulous post! I love it. But I really wanted the Michael Stars T shirt in red. I need it and only available in sizes too small or too big. Maybe I can settle for black.

    Thanks for the great post Cindy. Now if the weather improves I could wear things like this. Stuck in my winter wardrobe!

    • Cindy Hattersley says

      Hi Leslie

      Darn it! I can see you in that red tee…check eBay and poshmark. I just picked up a brand new black one there!

  11. Susan says

    Thanks for the interesting post on travelwear. I’m inspired also by your natural hair color and am attempting the same. Love the variety in your clothing selections and may look for the purse.

    • Cindy Hattersley says

      Hi Susan

      I have never regretted going silver. I hope you will feel the same way!!

  12. Jackie says

    I agree that you can’t go wrong packing black,
    and white with an accent color. Love what you put together, Cindy! I always add a couple long vests, too. They can be very versatile and go well with scarves.

    • Cindy Hattersley says

      Hi Jackie

      I think you can work with whatever neutral works for your coloring. I love long vests. They are so flattering, and LOVE scarves!

  13. Judy says

    Thanks so much for today’s post. It was perfect timing for my upcoming trip to Phoenix. I’m definitely going for mix & match using my color palette.

    • Cindy Hattersley says

      Hi Judy

      Have a wonderful time in Phoenix. The weather certainly has been challenging here!!

  14. Nancy T says

    I bought a pair of black pants, comfy tie waist with large zipper pockets from Target. I keep my passport, drivers license, global entry card with me at all times zipped up in my pants. Easy access to my cards, no digging in my purse. I do black white and tan with animal print scarves etc.

  15. Diane says

    What a terrific post, Cindy! I tend to overpack when I travel and this reminds me that I don’t need to have tons of clothes to look stylish. Thank you!

  16. LA CONTESSA says

    Whats with the red bag being tucked up under THY BOOB!
    You are ready for the GYPSIES in ITALY!
    ALL THE CLOTHING IS CUTE ON YOU…………..

  17. Cheryl P says

    I totally agree with your recommendation for packing black and white. I usually will wear comfy black stretchy pants while on the plane, with white t-shirt. Lots of mixing and matching during the trip, yes, simple, non-expensive jewelry, a pair of jeans, comfy tennis shoes (be sure you bring a “matched” pair, not like me who accidentally packed two different pairs of white tennis shoes and had to buy a pair for the rest of the trip!) LOL!

  18. dianne says

    super cute! You look adorable in everything, but I think my fave is the white Eileen Fisher top and cropped pants! Flattering and I love the white with your hair.
    We are renting a house in Carmel by the Sea for a month and I am really trying to pull together a bunch of cute things to take me through beach walks, dinners out, babysitting etc..
    I think the Eileen Fisher outfit will be perfect (Frank and Eileen has a similar one I am eyeing, too)
    Thanks, as always, for your inspiration!

  19. Karen says

    Cindy:
    These posts are wonderful, Thankful for ya
    honestly just got to a point of forgetting how to dress, as Winters, Renovations of the old farmhouse……… ( Nothing like when we resided in Big D.

    Love all of these ya featured.

    Thank you, Time, Work, Details, in each and every post, Fashion, Interior and Exterior decor, Gardening, Food💛💚🌷🌼

  20. Rose says

    Since I don’t wear black, white or navy, perhaps beige (I’m of fall coloration) brown and red? Love your casual style. And your smile.

    Thanks for sharing your vast wisdom.

    • Cath🇨🇦 says

      I’m with you there, Rose. Great collection but not the colours I can wear.
      I ‘d choose a warm beige as the base, wear brown leathers, and scarlet red & olive for colour pops. Black has been relegated to a few items, with colour around my face. White is too harsh for me.
      I have been having a lot of fun editing my clothes to wear mostly warm rich fall colours …I love colour!
      This collection is so helpful, but interchangeable with what works for each of us personally. A good reminder of editing before you close that suitcase 🧳 Thanks, Cindy

  21. Pat Cowan says

    Could you please tell us where to find the horn jewelry. Love your travel outfits!

      • Liana Hanson says

        This is so timely. I too have a black and white wardrobe with accents of red. My husband looked at your list and said you must have been in my closet! We are headed for Europe for a Rhine River cruise in May. I’ve been playing around with my wardrobe and discovered your post. I am Asian so the red accents are easy to come by. I already have similar items in my closet and I have come up with similar items. Our styles are similar. Thank you for this post. What is the link for the red purse you have in this capsule?

        • Cindy Hattersley says

          The purse is no longer available. It is MJ Wallace. I linked a very similar one. MJ Wallace is no doing one similar in pink…not my thing. I am so glad you found some inspiration and have a fabulous time on that cruise1. I can’t wait for Steve to get off his scooter so we can travel again! Going to Stanford today!

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