Transitional Dresses | Summer to Fall

Sheree Frede of the SheSheShow standing in front of trellis wall wearing a maxi red and white floral dress
Sheree Frede of the SheSheShow standing in front of trellis wall wearing a maxi red and white floral dress
Sheree Frede of the SheSheShow standing in front of trellis wall wearing a maxi red and white floral dress
Sheree Frede of the SheSheShow standing in front of trellis wall wearing a maxi red and white floral dress

Transitional clothing is my favorite! It’s perfect for summer and for fall and in between. With that being said, these dresses are not only transitional but VERSATILE! Below we have our favorite dresses for transitioning from summer to fall.

In Texas it is hot until mid October but I still want to feel like fall. So, I like to transition my brighter more colorful summer wardrobe into darker neutrals as we approach late August and September. It just gives me that fall feel even though it is 90 degrees outside. Most of what we have selected today are dresses the we can wear now in the heat and then later as we get into real fall like temps. If the dress allows layering then add a chunky cardigan or denim jacket with a cute pair of booties. Change out your straw handbag for a leather bag to complete the transition.

Transitional Dresses

Here are our top dresses to transition season to season!

1. Button Up Floral Maxi Dress

This dress is adorable and I love that it has a stretchy waist and the perfect length. I would pair this dress with these cute booties, this hat, and these sunglasses!

*Available in 38 other prints and colors!

2. Bohemian Midi Dress

How fun is this dress? You guys LOVED this dress last year and it even sold out! Well it’s back and I’m loving it again! I rock mine with sandals and to transition I like a knee high boot and these earrings.

*Available in 43 prints!

3. Rosalita Sheer Maxi Dress

This romantic maxi features a tie at the neck and a sheer lace finish. Cute with a bootie or trendy knee high boot like this one.

4.  Trapeze Maxi Dress

Is the print on this dress and pattern absolutely FABULOUS or what? To give this an edgy rockstar look how about these rockin’ booties and these earrings?

5. Floral Chiffon Dress

When you’re ready to show up as your most gorgeous self, all you need is this chiffon dress, some fab boots—and maybe a go-to lipstick. This 3/4-sleeve, midi-length beauty is perfected with a form-flattering fit, V-neckline and a flirty, moves-with-you hem!

6. V Neck Buttons Floral Maxi Dress

Looking for an affordable dress that’s a BEST SELLER?! Stop looking and here it is! This is the dress pictured and I’m LOVING it! It’s UNDER $35!

7. Button Up Split Maxi Dress

How cute is this button up dress? I love it with these knee high boots. To add some more flair to it, belt it with this trending obi belt and add these accessories!

8. Soft Surroundings Socorro Dress | SALE ALERT!

A free-spirited peasant maxi of soft jersey knit with exotic embroidery, a slimming smocked waist dotted with tiny beads, and tassel tie at the neck. Maxis are perfect year round, this one in particular is perfect to transition to fall. The fabric is thick enough that whether warm or cool you will feel comfortable in either season!

*****Soft Surroundings is also having a HUGE up to 50% off SALE! You can find this dress and many others on sale for little to nothing. I have definitely stocked up on my favorites by Soft Surroundings during this SALE!

9. Khaki Waisted Shirt Dress

Go to a great basic khaki colored shirt dress for the most versatility. You could wear it open over jeans, belt it with a statement leather belt, add a beautiful scarf, wear these cute leopard loafers, booties, boots or even sneakers. What a great investment this dress would be.

10. Chiffon Maxi Dress

Long, wide-cut dress in airy, crinkled chiffon. V-shaped opening at front with ties at neck. Dropped shoulders, long balloon sleeves with elasticized cuffs, and seam at hips and at knees. Detachable liner in jersey with a V-neck and narrow, adjustable shoulder straps. This is one of my favorite dresses to belt! I adore these booties to go along with!



  • It has rained every day since we have been back on Sanibel Island. Tis the season…. Headed out Tuesday for my first travel collaboration since last December. All of our activities will have COVID-19 in mind so they will be modified. We will do what is safe. Stay tuned…. lobster fishing! Have any of you ever been?
  • Gala’s, weddings, graduations, holidays or just everyday wear…..we have fashion suggestions for you, so stay tuned. Be sure to check out ShopSheShe tab at the top in the menu bar. Hover over and choose the category in the drop down. We try to keep it up to date with the latest and greatest for all budgets. Subscribe here and then you won’t miss a post. Simply enter your email in the pop-up box or below.
  • WELCOME new readers. We are a fashion/travel/lifestyle blog. We talk about anything and everything, from fashion, travel, health issues to even an occasional recipe. Let us know if there is a topic that interests you. We will do our best to bring that story to you. Have a great week sweet friends and thank you for following along. Without you, we could not continue on this crazy fun journey.

Being SheShe brings a huge responsibility to the midlife woman and I am definitely up to it!! I want to share with you what I have been exploring and trying to master for many years. I will say that there is no finish line, but it’s the journey……and I hope you will stick around for the adventure!!! -XO SheShe

SheShe’s Picks

Subscribe To Our Exclusive List!

Hi there sweet friends,

Thank you so much for taking the time to subscribe to my newsletter!

 You will get one email a week with a list of our blogs we posted plus SheShe’s Tidbits I always try to give you styling tips and tricks as well as shopping suggestions for every budget.

 Please check your SPAM folder if you do not receive the information. Let me know if you have any questions...

 Thanks again!

By submitting this form, you are consenting to receive marketing emails from: . You can revoke your consent to receive emails at any time by using the SafeUnsubscribe® link, found at the bottom of every email. Emails are serviced by Constant Contact

Leave a Comment