6 Ways to Wear a Midi Dress from Summer to Fall

A sleeveless dress is a classic summer piece. I got this one recently from Everlane (they sent it to me), and while the summer styling is kind of a no-brainer, I thought it could be fun to show how this type of dress could transition into cooler fall weather. Below I have 3 summer looks and 3 fall looks for you, all with the same dress.

In every outfit I’m wearing my Jaime Hoop Earrings in Mini Brass Squares, my three Yearly Co. bangles (I have two Initial Bangles with “J” and “L” on them for my kids’ initials, and a Twist Bangle) as well as my hammered gold ring Brian got me from J. Albrecht Designs in Colorado.

The exact dress I’m wearing is sold out in this color, but I found some other options for you to check out if you’re looking for something similar:


Jacket / Sandals / Tote / Similar hat

This is an easy, breezy summer look that gets elevated with a high end tote. The baseball cap is perfect for hiding unwashed hair, and the denim jacket helps to define the waist.

Hat / Similar bag / Mules

Sometimes in the summer heat you just want to wear a loose dress, and this look is perfect for that. No belt or belt bag, but the crossbody creates a nice line across the body and creates some shape.

Similar belt bag / Mules

This is the very first way I styled this dress when I wore it. I love it with a belt bag (as you’ll see below!), and these mules work really well here because they are similar in color to my skin and help extend my leg line.


Sweater (c/o) / Similar belt bag / Mules

This is the first of 3 looks that applies the same concept: layer a sweater over it and tuck it into a belt bag. It’s easy, it’s simple, and it works.

Sweater / Similar belt bag / Mules

Ta-da! I did it again. I love how leopard works as a neutral—it mixes so well with the olive green! I found this sweater on Poshmark when it was sold out in my size and I’m so glad I ended up getting it. I had a dupe that was nowhere near as good!! I went up a size for the perfect fit.

Sweater (c/o) / Similar belt bag / Similar slingbacks (also similar)

Last look (once again, with a belt bag). These slingback booties are very old, and whenever I think about getting rid of them I hesitate because they are really perfect with dresses that are this length. There’s something about the slingback style that just works better than a traditional ankle boot for me here.

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  1. 11.28.19
    Lisa said:

    Great article! These are different ways to wear midi dress in summer. I want to wear my summer dress in winter too and I got great idea from your blog. I am so excited to try those styles. Thanks and keep sharing.