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Stylish Ways to Transition Linen to Fall

It is no secret I love the comfort and versatility of linen. Today I am joining my friend Kim for our monthly Signature Style Series. In many parts of the country it is easy to transition your favorite linen pieces into fall. Linen can be worn year round here. Let’s talk about Stylish Ways to Transition Linen to Fall.

The key to transitioning your linen clothes into fall is to add layers and change up your accessories. Let’s take a look at some outfit ideas.

I shared this Eileen Fisher Organic Linen Delave top in my post Chic Effortless Packing Tips for a 10 Day Getaway where I styled it like this for summer.

Eileen Fisher gray sweater and tank j jill linen pants


Here I styled it over a column of black, including the Eileen Fisher Linen pants and a favorite Michael Stars tee with my mongrammed velvet birdies. The bracelet is vintage and the necklace from Paula Carvalho designs.

Eileen Fisher Delave Top styled for fall by Cindy Hattersley


I have had this linen dress from Linennaive on Etsy for several years. Here I am wearing it with the cream linen max mara jacket ( life jacket (customized by cara brown designs), and korkease sandals. Necklace from Paula Carvalho.

over 50 style blogger cindy hattersley in Etsy Linen Dress, Life Jacket and Brador Sandals


Add a sleeveless t-shirt dress or turtleneck, to the summer dress as a base layer, with a fun hat and wear it as a duster for the colder months. The leopard mules are from Madewell (sold out) but you can find them on eBay here. I also linked similar below.

cindy hattersley in Target lbd with linen dress over it


I love my lily linen skirts (on sale here), (I have linked some from eBay below as well),a cotton blouse from Auntie Oti (no longer avallable), brixton hat, and dragon diffusion tote.

Over 50 Style Blogger Cindy Hattersley In CP Shades & Cara Brown Designs Life Jacket


The mustard lily linen skirt I have owned for years. Below I am wearing it with a leopard J Crew shirt and my vintage moto jacket. You can find similar leather moto jackets on Nordstrom here, or on eBay here.

Fall Trends that those of us over 50 can actually wear


This photo is from a few years back as well. I am wearing the same skirt with a denim jacket.

cindy hattersley in cp shades lily skirt and denim jacket


I am wearing my life jacket with jeans and a lightweight linen top from Tancredi & Morgen and my blazer. I am wearing birdies, but a cute ankle boot would work as well.

cindy hattersley in J Jill Jeans-cara brown life jacket


I updated a column of black (Eileen Fisher linen pants & michael stars tee) with a lovely scarf from Eileen Fisher with my vintage turquoise Native American jewelry and birdies loafers. I styled this scarf in my post How to Make Sweatpants Look Chic here. You can find similar necklaces on eBay here.

eileen fisher linen pants and scarf-michael stars tee


This neutral Oatmeal linen dress from Eileen Fisher can be styled multiple ways into fall. Here I am wearing it with tights, sandals and a favorite bag. You can see how I styled this dress in my post Ten Fresh Ways to Style Black and White here, and Multiple Ways to Style a Capsule Wardrobe here. You could switch out the sandals for a pair of birdies or booties as well.

cindy hattersley in Eileen Fisher tunic, leggings, helen kaminski hat and leggings


This ensemble could easily be changed up for fall by adding a tee with long sleeves in either black or camel. The sandals could be changed out to boots, as the weather cools.

cindy hattersley in eileen fisher terry midi and delave top


This linen cotton sweater also would pair well with the lily skirt and a pair of short booties or tall boots.

Eileen Fisher linen cotton sweater, lily skirt, and ankle boots


Last but not least the Eileen Fisher Long Linen Poncho could be paired with a long sleeve tee and leggings for fall. I wore this outfit on the plane recently.



I hope this post has inspired you to look in your closet, grab your linen garments and wear them into fall. Linen is a natural fabric that can be worn well into fall, if you add some layers for warmth. You might also like to take a peek at my post from last year Five Tips on How to Transition Linen Apparel into Fall.

Now let’s pop over and visit Kim to see how she is styling her linen.


Reader Interactions


  1. Rita says

    Thank you for always taking the time to show us actual photos of your outfits rather than just providing a link. Your ideas are so helpful and perfect for living in the Southwest!

  2. Barb L says

    You look terrific in each outfit. Love the mesh top and the CP skirt. Slowly adding linen to my closet (late to the party) and I am also loving gauze. So much more comfortable on the hot/humid days. On another note…I have also stopped using fabric softener and have substituted white vinegar. So happy with the results (and my washer is cleaner too)

  3. sharon says

    Cindy, do you have the CP shades skirts hemmed? Do they come in petite? It appears that they would be difficult to hem because of the volume. Thanks for your lovely posts. You are one of my favorite bloggers, whether it is fashion or design.

  4. Charlotte says

    Love your posts!! Thanks for introducing me to CPShades. I purchased the lily almond skirt on sale and absolutely love it

  5. Susan says

    Are the Michael Stars tee shirts all that you say they are? I need a few good tee shirts, but they seem pricy.

  6. Juliet says

    Cindy, I think of you as the queen of linen … always light, airy and fabulous. Pairing linen pieces with denim and leather is so good and that photo of you in the leather jacket is fire! That does it, I need more linen in my life. Off to shop your links. xo

  7. Wren says

    I think you know I’m a sucker for linen. I bought the mesh short pullover from EF, which, unfortunately was not on sale. I was torn between getting black or silver but I ended up deciding on black. I love how it layers (and can hide upper arms) without adding a lot of weight. All of your looks are terrific and we need that fabric where we live on the hot days, wrinkles and all!

  8. Elizabeth@pineconesandacorns says

    Linen is a comfortable and versatile look and fabric. I love it for Spring/Summer and Fall. Thanks for the tips for extending our wear into Fall.

  9. LA CONTESSA says

    YOU really pull it together with your horn bracelets and accessories!
    I wear linen all the time as you know!

    • Cindy Hattersley says

      Hi Eliz

      It is our favorite! You are the one who introduced me to Bryn Walker!!

  10. Kim says

    Cindy you did a fantastic job on this post and continue to come up with inventive and beautiful ways to style your clothes. I love the way you layer of these cute mesh pieces over things! I also love all your linen skirts. They look so good and I need to find one. I was considering buying one of the pull on bias cut ones, but I also like the ones with the full skirt with the cute little jackets
    you show with them. That is so flattering and pretty!
    You look beautiful on all these. Great tips for layering into the colder months! I am going to wear my wider leg linen pants with chunky sweaters and sneakers I think. Thanks for all the fab inspiration as always!
    Love doing this with you. xo

    • Cindy Hattersley says

      Hi Vaughan

      Shirts or skirts? I don’t think so, but I realize the length needs to be perfect!

  11. Pam says

    I love that you always style so many pieces which gives us so many wonderful ideas for our own wardrobe. I started wearing Chico’s no iron linen shirts a few years ago to ease my way into linen. This year I made the plunge and bought several pairs of wider leg linen pants and love them. I don’t like that I usually have to steam them before each wearing, but I am doing it anyway because I like the lightness and comfort of them. I just love your blog❤️

    • Cindy Hattersley says

      Hi Pam

      I embrace the wrinkles and favor the brands that like them wrinkled. The J Jill pants I give a quick run over with the iron.

  12. Gretchen P Montgomery says

    One more question! How do you determine your size in the BROTHER’S INDIA shirts? You are amazing! What a find!

    • Cindy Hattersley says

      Hi Gretchen

      I would contact the shop owners. I am tying at the waist so I don’t mind them being large. I can wear a small mens.

  13. Gretchen P Montgomery says

    When you have a moment, would you let me know what the vine is in the picture where you are wearing the duster and your hand is on your hat? You can wear anything, and it looks perfect!

    • Cindy Hattersley says

      Hi Gretchen

      It is morning glory! It has the most beautiful blue flowers when it blooms.

  14. Dinah M says

    I live in Houston, the perfect climate for linen year round. But I resist buying it because it wrinkles, and I cannot forget my mother telling me ” you look like an unmade bed!” I honestly cannot stand ironing these garments, only to have them wrinkle the minute I put them on….so they hang in my closet, unworn. And sending them to the cleaners is $$$$. Yet, there are many who wear linen, and never complain. How do you care for your linen garments?

      • Dinah M says

        Actually, YES. I feel rumpled and sloppy when my clothes are very wrinkled. Mind you, I wear cotton blouses and slacks and they also wrinkle, just not as much. My daughter wears a lot of linen, and has NO problems never ironing any of it. I never think she looks disheveled, but she is a lot younger and looks great in everything she wears. I think it is a mind set that I learned and just hold on to!

        • Vicky says

          Let me help, Dinah. I once read we should view them as aristocratic wrinkles. Once you see how wildly comfortable linen is, you’ll never look back!

    • Cindy Hattersley says

      Hi Dinah

      I wash them with no fabric softener and hang them up outside wet. I pull and yank them into shape. Sometimes I lightly iron them while wet depending on the brand. CP shades and many others are to be worn natural. I never send anything to the cleaners except maybe a wool coat. I quit using fabric softener (I use the wool balls) and embrace the beauty of the natural fabrics.

      • Dinah M says

        Aha! I knew you had to be doing something to your clothes to make them look so perfect. I do something similar with my linen napkins (take them out of the washer wet, spread them out flat with my hands, and they dry naturally). But….those are small pieces of fabric, not a dress or skirt. I do have several linen dresses, and I think ironing them might be a bit easier than the “hand pressing” I do with my napkins. I will give it a try, however, and see if I like the results. Thanks, Cindy

  15. Karen B. says

    I confess, your love of linen has rubbed off. I used to avoid it due to the wrinkles, but as I’ve added a few pieces I’ve found it doesn’t wrinkle as badly as I thought and it’s so comfortable.
    The older picture of you with the leather jacket made me smile. You look like a top woman executive who no one should mess with. Hahaha. Not that you couldn’t be serious, but you always share your delightful smile and it’s such a telling sign of your kindness and fun-loving nature. 😊
    Have a good week. I’m headed to Seattle at the end of the week. It should be a welcome change from the heat.
    Karen B.

    • Cindy Hattersley says

      Hi Karen

      Linen is soooo comfortable, breathable and very strong. That picture is funny! I can’t remember who snapped it?!! I know it was hot while we were gone. It cooled down here last night. Have fun in Seattle…such a beautiful time of year to go!

  16. Lee Davison says

    Linen is perfect for us in warmer climates. Using some of your tips will help make my linen wardrobe go way into fall.

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