How to Transition a Summer Dress into Fall

It’s the first Tuesday of the month and that means it’s time for another party with my 9 cohosts of the Ageless Style Linkup. This month we’re each of us over 40 somethings are showing you how we transition a summer skirt into fall. It’s always exciting for us to see how the others interpret the theme for the month. I for one, am going to check them all out because I love getting inspired to create between season outfits.

Between season outfits can be tricky when we’re not quite ready to banish cute summer skirts and dresses to cold, dark winter storage. Today I’m going to show you how I took ONE summer dress (because I’m a rebel like that and chose to style a dress instead of a skirt) and created TWO between season outfits with just a few items I already owned.

You Can’t Stop Mother Nature

Summer is quickly coming to an end and while I’m looking forward to a little slow down and for nature to put on one of her best shows, I might be kicking and screaming a little. We’ve had such a good first summer here at The Cedar Palace with our Grand-Littles enjoying time in the pool and playing in the big yard. It went way too fast!

Try as I might though, fall is on the way. Here in Northern Indiana they are forecasting temps in the 60’s this week with overnight lows in the 40’s! YIKES! Indiana’s not the warmest place on earth, but that’s cooler than normal for this time of year here too.

I’m not in a super big hurry to pull out my flannel and long underwear because winter is really long around these parts. I’ll have plenty of time to grow tired of winter wear. So, I’m going to get a bit more longevity out of some of my summer dresses. If you don’t know how much I’ve loved dresses this summer, you can read about it here.


If you use a bit of creativity, I believe that you can take one or more of your summer dresses or skirts and create between season outfits that will take you from early to late fall. And it might surprise you to know that you probably have most of the components already in your closet. High-five for shopping our closets!

I’ve created two between season outfits here without spending one thin dime! That doesn’t mean I’m not eyeing up a new felt hat and a couple of long cardigans that will come in handy in lots of wardrobe ensembles this fall and winter. You can see (and shop) some of my wish list items below.

Between Season Outfit / Summer to fall transition outfit / Fall Fashion /

I’ve used this super sweet knit Easton dress from Aventura Clothing for this challenge in the gray/green color.  The high waistline is perfect for hiding food (or menopause) babies, though it may accentuate the girls a little. 😉

I styled it for a day out and about earlier this summer (here). You could easily do this with any sheath or swing dress that is solid or even striped. Or go crazy and wear certain summer florals with a chunky sweater…. Oh MY,  the sky’s the limit!

Summer to fall outfit / Between season outfit /

Between season outfit / summer to fall dressing

If fashion can’t be FUN, don’t wear it!

Between season outfit / summer to fall outfit /

I kept telling The Hubs that I thought I was too “boobalicious” for the dress…. The G-Sisters just wouldn’t stay behind the kimono. 😉

Early Fall

I’ve added this Sole Society kimono that has some beautiful greens in it because it’s another piece I LOVE and am not yet ready to retire for the season. However, I think this would be a perfect opportunity to add some of the dark florals that are so popular this fall.

Booties…. Of course!

between season outfit / fashion over 50 / ageless style linkup /

Slightly heavier jewelry can pull it all together. Thanks to nasty hot flashes and what I’ve come to believe are some self-diagnosed “sensory issues”, I don’t tend to wear a ton of jewelry in the summer, especially necklaces. Cooler temps give me the opportunity to add some larger pieces (though still not really physically heavy) in warmer Autumnal tones of gold and beige.

A richer colored handbag can also give your fall fashion a warmer vibe.

Late fall outfit / summer to fall outfit / fall fashion

Fall fashion / summer to fall fashion / 1 summer dress - 2 fall outfits /

Late Fall

Change out the kimono for a cozy long cardigan. I switched my booties for tall boots and I’m ready when fall is leaning in closer to old man winter, which may not too far away this year. If you have trouble finding boots for wide calves like I do, I wrote about that here.

I kept the cardigan long so that there was no question of what length I was going for. Keep your own proportions in mind, but I think the cardigan can even be longer than your dress.

Fall fashion / summer to fall fashion / fall outfit /

Don’t forget Your HAT!

Seriously! A felt hat can really make the season transitioning look WERK. They are a really fun addition to most any outfit. You say, “I don’t look good in hats.”  Be a little daring and keep trying them on. There is one that will look good on you. You don’t have to spend a ton of money on a hat that you won’t wear all the time. Target, TJ Maxx and Marshalls are all great places to find trendy hats for good prices.

Mix it UP ! Link it UP!

Be sure to head on down and check out the other blogger babes for more inspiration to get in those closets and create between season outfits that are uniquely YOU! Have a blast shopping your closet and saving a little cash in the process. You’ll feel super frugal and cute heading into your local coffee shop with some extra change in your pocket for a pumpkin spice…. anything. Or to buy that cute fall hat! (I might be drooling over this one.)

Tell me, what’s your one summer wardrobe item you’re most sad to put away? And what are you looking most forward to wearing this fall?

Happy (Almost) Fall Y’all!


You might want to take a look at these *……


And LOOK at these lovelies for more style inspiration…..
ageless style/ fashion over 50


  • Have fun and make some new friends! Please visit at least 2 other links.
  • Please link to your actual post and not your blog’s homepage.
  • Please link back to the Ageless Style Link Up in your linked post.
  • Feel free to use #AgelessStyleBloggers in all of your social media posts
  • Please follow each of your hosts on at least one social media channel via the links below.

Ana ~ Mrs. American Made blog, bloglovin, instagram, pinterest, twitter, facebook

Daenel ~ Living outside the stacks blog, instagram, pinterest, twitter

Debbie ~ Fashion Fairy Dust bloglovin, instagram, pinterest, facebook, twitter

Jennie ~ A Pocketful of Polka Dots blog, instagram, twitter, bloglovin

Jill ~ Doused in Pink blog, pinterest, facebook, instagram, twitter, bloglovin

Jodie ~ Jodie’s Touch of Style blog, facebook, instagram, pinterest, bloglovin, twitter

Nicole ~ High Latitude Style blog, pinterest, twitter,facebook, google, instagram

Paula ~ Dimples on my What blog, facebook, Pinterest, Instagram, twitter

Shelly ~ The Queen in Between blog, instagram, bloglovin, Pinterest, facebook

Yvonne ~ Funky Forty blog, twitter,, bloglovin, instagram, pinterest


  • This post may contain some affiliate links. Even though I might make a small amount from the affiliate program, you won’t pay a cent more for the product. And as always, it FREE to look! 😉

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.


  1. Paula, I am loving that kimono! But then I have quite the kimono addiction. And being an “H” girl myself, I feel you on the kimono not staying closed over the boobs! I also love the way you transitioned the dress to the fall with tall boots and a sweater. Super cute!


    • Paula

      Thanks so much Shelbee. It’s always a challenge to keep the sisters from being a “Girls Gone Wild” show. I usually will style a kimono with tank or tee that skims and flows a little more. 😉

  2. And of course a jean jacket always work too 😉 Love your ideas and that floppy hat!

    • Paula

      I agree about the jean jacket of course! I was trying to think outside of my usual box. 😉

  3. /

    Perfect transition dress and you wear it so very well. Enjoy September. . .

  4. /

    In my neck of the woods, the temps won’t be dropping much below 80 for several more weeks so I can only dream of the Fall weather and fashions that I love so much. The second look with boots and cardigan is my dream outfit and one that I would wear year-round if the weather would allow.


  5. This dress is a knockout on you…. can you BE too boobalicious? I doubt it!
    Your layering is perfect, right up my street.
    Thank you so much for linking this post up!

  6. Suzy

    Hello Paula, I’m so glad I found you this morning. It’s very nice to met you. You look like lots of fun!

  7. /

    First, have to say how cool it is that you all do this! I love seeing everyone’s take on it!
    Now, let me say how much you ROCKED this! Loved every little thing about it! Both looks were just dead on, suited you so well! And it was fun to read! What a great way to end my night! 😊

  8. I love the gray booties you are wearing. I like the way the top kind of forms a vee, I have chunky ankles but think I could wear these. Could you tell where they came from? Love the dress also. Great styling.

    • Paula

      Hi Victoria! I love this style of bootie as well. It’s more flattering on a full calf too. These are Carlos Santana Bootie that I can no longer find. I have another similar style in another color that are Report. If I find something similar I will do my best to link them in an upcoming post. I did find a Born booties last year that has a higher shaft but has the slight dip in the front. Anything that is asymmetrical or as a cut out in the front will leave a little room. Also, consider these: I purchased them yesterday and they are pretty flattering especially with a pant that hits just above the ankle.

  9. /

    That dress is darling on you! Perfect your fall styling! Your kimono is so pretty and I love your orange sweater!

    Doused in Pink

Share via
Copy link
Powered by Social Snap