3 Ways to Style a Midi Shirtdress Now & Into Fall

3 Ways to Style a Midi Shirtdress for Now & Into the Fall Season | Louella Reese

I am always on the mission to find pieces that can be worn several ways. As well as transition into several seasons, at least two. To me, each purchase is an investment – whether it is a big or small one – and I want to make sure I am making a good investment. That the piece will be worn often and won’t have to be worn the same way every time I wear it. I like versatility and getting my money’s worth out of an item. PLUS if the pieces that fill my closet can easily be mixed and matched, worn several ways, and within several seasons, I don’t need as many items!

I’m a big fan of dresses. There is no question about it! I love how easy they are, how comfortable they can be, and of course the feminine aspect of a dress. However, sometimes, dresses can be hard to rewear/restyle. Not because they can’t be but simply because we don’t see the restyling possibilities. Exception: bridesmaid dresses – no she will not hem it and rewear it.

So with that being said, I wanted to share a recent midi shirtdress I purchased and have already worn several ways to provide you with some styling inspiration.

3 Ways to Style a Midi Shirtdress

Here are three ways to style a midi shirtdress (which would also work for a simple shirt dress or casual midi dress) for now and later into the fall season. From straw totes, to sneakers and nude flats, these are easy to recreate looks. There’s something for everyone here. From feminine and dressy to casual and easy.

When it comes to dresses that are easy to restyle my recommendation is to opt for a solid color or a more casual fabric like cotton. Doing so provides you with a blank canvas to add pops of color and character with the accessories you choose.

For End of Summer

An easy, casual, and feminine end of summer look. A straw hat, straw tote, and espadrille flats. The quintessential pieces of summer that happen to pair perfectly with a midi shirt dress (or any shirt or more casual midi dress). For a little pop of color, add a bandana to your straw tote.

See a slight variation of this styling I wore during our late of summer soiree.

shop the look

tiered white midi shirtdress | straw hat (also available here) | straw tote | espadrille loafers

Dressed Down with Sneakers

Okay so truthfully, this is my favorite styling and my absolute go to! There is honestly not a better combination in my opinion than a dress with sneakers and a wide brim hat. This combination is also perfect to wear now as summer comes to an end as well as into the fall season! A chunky knit cardigan or cropped crewneck would be the perfect addition when extra warmth is needed.

shop the look

tiered white midi shirtdress | wool rancher hat | c/o paravel capsule bag | round frame sunglasses | similar white platform sneakers

Dressed Up for Fall

The sweetest of the three and the most dressed up styling. Simple pointy toed nude flats and a ladylike top handle bag makes this feminine and dressy. If you want to have a little more fun with your footwear I think a jewel tone or metallic would be perfect as well.

shop the look

tiered white midi shirtdress | c/o neely & chloe handbag | nude pointy toed flats

photos by Natalie E. Photography


  1. Kileen wrote:

    I love this style of dresses so much! They are so perfect for fall. I love this dress by the way!


    Posted 9.17.20
  2. rebecca wrote:

    I already told you this, but this is your perfect dress! I definitely love the look with the sneaks best but they are all cute.

    xx reb // thecrystalpress.com/blog

    Posted 9.17.20
  3. Morgan wrote:

    You are the best at styling things multiple ways!! Making your wardrobe stretch to the fullest. I love it!

    the HER chronicles [] http://theherchronicles.com

    Posted 9.17.20
    • thanks girl friend! needed that phrase when I was writing the post haha – definitely was what I was trying to say.

      xo Laura Leigh

      Posted 9.18.20
  4. I think I need to finally take the plunge and snag this dress!! I love how you can style it so many different ways!

    Posted 9.18.20
  5. Anna English wrote:

    I know I already wrote this on your IG post, but I’m obsessed with the sleeves of that dress! So cute!

    Posted 9.18.20
    • girl I am with you and have probably told my husband that 100x so don’t worry – I get saying it again 🙂

      xo Laura Leigh

      Posted 9.18.20
  6. I don’t wear dresses much, but if I do, I’m definitely gravitating to easy and effortless styles like this. Love it! xoxo, Sarah

    Posted 9.18.20
  7. Stephanie wrote:

    I had to laugh really hard because you mentioned how no one will ever wear their bridesmaid dress again, and my best friend texted me the other day with photos… of her wearing the bridesmaids dress she wore in my wedding to an event! I guess there are exceptions sometimes 😉 But I love love this shirtdress and it makes me want to invest in one myself to wear from the end of summer into early autumn!

    Posted 9.18.20
    • haha I love it – that is great! thank you so much 🙂 it is definitely worth the investment as they are so versatile!

      xo Laura Leigh

      Posted 9.18.20
  8. Lizzie wrote:

    So many cute ideas! I love all of them! That dress is the perfect base for styling!


    Posted 9.18.20
  9. Greta wrote:

    A good shirtdress is so versatile and can be worn so many ways! This is so cute with booties and sneakers.

    Posted 9.18.20
  10. Love your white dress so much!
    Thanks for sharing

    Posted 9.21.20
  11. Marlene wrote:

    Ok I am so obsessed with that bag!! What a cute find. The dress looks lovely on you

    Posted 9.28.20

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