7 Ways to Wear a Midi Skirt from Summer to Fall

This is the first year that I’m fully embracing midi skirts. This high slit style is my favorite because it doesn’t make me look shorter the way traditional midi skirts tend to, and the slit also allows more movement without it being a fuller skirt style. It’s a real winner for me!

This is my exact skirt, and here are some similar options that could easily work for these looks:

In all of these looks I’m wearing my Julia Earrings in Matte Gold Teardrop (available September 5th), 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 from J. Albrecht Designs. One thing I don’t usually mention but might start adding is sunglasses—I wear them everyday! For these outfits, I’d wear these matte black sunnies. Everything is true to size unless otherwise noted.

Sweater tank / Bag (and similar) / Mules

This sweater tank is a new favorite of mine that I already bought in another color because it’s THAT GOOD. It’s a perfect piece for San Diego fall since it doesn’t cool down until late October, plus this coppery/rusty red hue is a new favorite of mine. For the belt bag, I went down a size so I could wear it up high on the waist.

Cami tank / Jacket / Mules / Tote

This is my favorite look of all of them—I like the mix of brown and black and denim, and the way the denim jacket and mules add a casual tone to a skirt and tank that could otherwise read as dressier. I think the jacket runs small and I went up a size for the perfect fit. It’s been such a good summer layer! I went up 1/2 size in the mules but I think you could stay true to size if you don’t have wide feet—they’re roomier than my other Madewell mules. For the cami, I recommend going up a size if in doubt since it doesn’t have stretch and isn’t intended to be fitted.

Tee (and similar) / Bag (and similar) / Sneakers

This is one of my “cool mom on the playground” looks—sneakers and a tee keep it comfy and practical for chasing toddlers around, but the skirt and fun bag add a chic factor.

Bodysuit (c/o) / Belt bag / Sandals

This has been my go-to summer look with this skirt—a simple bodysuit, belt bag and flats. Easy!

Shirt / Bag (similar and similar) / Mules

Did I already claim a favorite? Oh shoot, I did. Okay, well make a tie then because I really am into this one! This button-down is a recent purchase to replace an older one that was more fitted and I’ve already been able to work it into my wardrobe several different ways. A white button down is a classic, and I love the drapey fit (I did size down since it’s oversized!). This one is a great option for a not-too-hot summer day or those early fall days when the weather is just starting to cool down.

Bodysuit (c/o) / Bag (c/o, and similar) / Mules

Everlane sent over this bodysuit this month (also have it in stripe!) and I love it with this midi skirt to ease into fall. Bodysuits are such a good match with skirts!

Similar sweater / Belt bag / Mules

A sweater and midi skirt is another great fall transition option. I used a belt bag here to help crop the sweater at the right spot to be sure I didn’t lose my waistline. This look would also work with a tan bag and shoes for a lighter color scheme. The mules definitely run narrow so I recommend sizing up 1/2 size. The sweater I’m wearing here is from last year at Target, and while it was a good find and is comfortable, Everlane sent me a similar one that is higher quality and has a better fit, so I linked that one for you (TTS).

Are you into midi skirts? Which look is your favorite?

P.S. 7 ways to style a leopard midi skirt

Leave a Comment


  1. 9.26.19
    Anonymous said:

    Hi there! Love these outfits and that beautiful framed print. Mind sharing details on that? thanks!

  2. 8.21.19
    Julie said:

    Hi Natalie! I just had a quick question about how you style sweaters over skirts or dresses. If you don’t have a belt bag and wouldn’t be able to pull it off at work (it would get in the way), how would you go about creating a waist with a sweater over a dress or skirt? Thanks!

    • 8.22.19
      Natalie said:

      You could use a regular belt for a similar vibe! Or sometimes if a sweater isn’t too bulky I create a fake “knot” using a clear elastic hair tie.