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.

1 SUMMER Dress Transitions into 2 Fall Outfits / Between Season Outfits / Fall Outfits /

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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.

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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!

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Between season outfit / summer to fall dressing

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

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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!

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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.

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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.

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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


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