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Three Ways To Style A Midi Dress For Fall

  • October 1, 2021
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ashley wearing a navy blue floral midi skirt with a skinny belt at the waist and cognac ankle boots

In this post, I’m showing you three ways to style a midi dress for fall. When I was creating my fall capsule, I knew I wanted to add a floral midi dress. I usually tend to go toward more masculine pieces and structured silhouettes, but I like having a few feminine pieces to pull out when the mood strikes.

As always, before I add anything to my wardrobe, I think about different ways to style it with pieces I already own. For this piece, I came up with three different looks, one casual everyday look, one dressed up option, and one edgy look.

This exact dress is from a local boutique in our city called The Pretty Posy. Check out their shop if you’re local! However, I am linking several gorgeous midi dress options below that are available online from my favorite retailers, too. I particularly love the ones with dark, moody, florals and long sleeves.


Three Ways To Style A Midi Dress For Fall

LOOK ONE: Midi Dress With Sneakers And Tote Bag
ashley wearing a navy blue floral midi dress, paisley canvas tote bag and white sneakers
Midi Dress (similar options linked below) // Sneakers (limited stock, similar) // Bag (old, similar, similar)

I love how these days you can pair ANYTHING with sneakers and call it a look. This is my casual, everyday look for when I need to feel comfortable. I’m obsessed with wearing my white sneakers with dresses. It’s just the cutest combo ever. I added a little canvas tote bag for this look and have my hair in a low pony. This mama’s ready for the day.

LOOK TWO: Midi Dress With Faux Leather Jacket And Chelsea Boots
ashley wearing a black faux leather moto jacket, navy floral midi dress, and black lug sole chelsea boots
Midi Dress (similar options linked below) // Faux Leather Moto Jacket // Chelsea Boots (limited stock, similar)

This edgy look was a little outside my comfort zone, but I’m actually kind of into it. The contrast of the faux leather moto jacket and black boots with the flowy floral dress is super on trend right now, and really just looks kind of cool.

LOOK THREE: Midi Dress With A Belt And Ankle Boots
ashley wearing a navy floral midi dress belted at the waist with brown ankle boots
Midi Dress (similar options linked below) // Belt (old, similar) // Boots

I just love this look; it’s perfect for fall. These boots are new from ABLE (see more about them here), and I’m obsessed with them. This combo would be adorable for fall family photos, too.

ashley wearing a navy floral midi dress belted at the waist and brown ankle boots
ashley walking down a sidewalk wearing a navy floral midi dress belted at the waist and brown ankle boots
a waist down picture of Ashley wearing a navy floral midi dress and brown ankle boots

If you found this post useful, you can check out this post on how to style plaid blazers for fall. I’ll be posting more fall style content this season too so check back!

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2 comments
  1. Aunt Judy says:
    October 3, 2021 at 6:09 pm

    I like the edgy look!!

  2. Pingback: How To Style Ankle Boots For Fall - Stitch & Salt

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