T-Shirt Midi Dress Styled Two Ways – Summer & Fall

One t-shirt midi dress styled two ways, for two seasons! How to wear the dress now and later into the fall season. 

T-Shirt Midi Dress Styled Two Ways | One Dress Two Seasons - How to Style for Summer and then into the Fall Season | Louella Reese

Look 1: Anthropologie Sundry Ayana Midi Dress | c/o Kelly Wynne Clear Convertible Crossbody & Belt Bag | c/o everlane Day Crossover Leather Sandal | c/o jj Leigh rattan earrings | David Yurman cable cuff |David Yurman cable ring

Happy Friday! Oh how I love when Friday rolls around. And this week is came very quickly! Which I’m not too upset about. My to do list on the other hand, could definitely use another week day. But oh well, there is always next week right?

With it almost being the weekend, I thought it was appropriate to share what will be your new go to weekend uniform! The base, this super comfy t-shirt midi dress. It’s one of those pieces you want to absolutely live in! While being super comfortable it’s also really cute. Much cuter than a pair of workout shorts and your favorite, very lived in tee shirt. A piece that’ll take you from day to date night with just the switch of a couple accessories. 

As well as take you from summer to fall…

T-Shirt Midi Dress Styled Two Ways | One Dress Two Seasons - How to Style for Summer and then into the Fall Season | Louella Reese
Rattan Earrings, Summer Earrings | Louella Reese
Clear Belt Bag, Clear Waist Bags | Stylish Game Day Bags | Louella Reese
T-Shirt Midi Dress Styled Two Ways | One Dress Two Seasons - How to Style for Summer and then into the Fall Season | Louella Reese

Look 1: Anthropologie Sundry Ayana Midi Dress | c/o Kelly Wynne Clear Convertible Crossbody & Belt Bag | c/o everlane Day Crossover Leather Sandal | c/o jj Leigh rattan earrings | David Yurman cable cuff |David Yurman cable ring

I said this before, I’ll say it again…summer is FAR from over in Charlotte – the south in general. We still have a good three plus weeks of it. Therefore, we sadly still have to dress for it vs. pulling out all of the sweaters and cozy pieces. So I say, let’s have a little fun with it and slowly make the transition. 

Enter in the t-shirt midi dress of your dreams! It comes in two darker hues – the navy you see me wearing and a sage green. To me the green looks a little lighter online than it is in person. Either way both colors are perfect for the transition time in between summer and fall. Wear now and later! 

So to style the piece for now, I paired it with my new favorite bag, this clear belt bag, and a pair of white leather sandals that I basically wear every single day. I personally love how the belt bag creates a waist and gives the dress a little more shape. 

T-Shirt Midi Dress Styled Two Ways | One Dress Two Seasons - How to Style for Summer and then into the Fall Season | Louella Reese

Look 2: Anthropologie Sundry Ayana Midi Dress | Madwell Canvas Backpack (similar, my exact one has sold out) | Veja V-10 Sneakersc/o jj Leigh rattan earrings | David Yurman cable cuff |David Yurman cable ring

For fall, I went ultra casual. Pairing the dress with a great pair of white sneakers (seriously they’re the comfiest pair I’ve ever owned), an easy sweatshirt, and canvas backpack. Perfect for running errands, working from a coffee, shop, or exploring a new town (or your own). 

I again created a waist by tying the sweatshirt around my waist. I meant to take a couple photos to show y’all what it would look like with the sweatshirt actually on but the heat got the best of me and I didn’t think about it. It is a cropped hoodie though so it still cinches in at the waist. Which I think is important when pairing something over a dress like this. You don’t want to come across to messy/slouchy. 

T-Shirt Midi Dress Styled Two Ways | One Dress Two Seasons - How to Style for Summer and then into the Fall Season | Louella Reese
Casual Midi Dress, Late Summer Dress to Transition into Fall | Louella Reese
Casual Midi Dress, Late Summer Dress to Transition into Fall | Louella Reese
T-Shirt Midi Dress Styled Two Ways | One Dress Two Seasons - How to Style for Summer and then into the Fall Season | Louella Reese

Look 2: Anthropologie Sundry Ayana Midi Dress | Madwell Canvas Backpack (similar, my exact one has sold out) | Veja V-10 Sneakersc/o jj Leigh rattan earrings | David Yurman cable cuff |David Yurman cable ring

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28 Comments

  1. Morgan wrote:

    Love when an item can we styled for multiple seasons! The ruffle sleeves make this dress so darling!

    -Morgan
    How 2 Wear It [] http://how2wearit.com

    Posted 9.13.19 Reply
  2. lee wrote:

    such a pretty dress! I love the second way you styled it!

    Posted 9.14.19 Reply
  3. Rach wrote:

    How cute is that dress! I love how you styled and also really like your belt bag!

    http://www.rdsobsessions.com

    Posted 9.16.19 Reply
    • Thanks Rach! The belt bag is my new obsession – pretty darn psyched about it and make every excuse to wear it!

      xo Laura Leigh

      Posted 9.16.19 Reply
  4. I’m a huge fan of tshirt dresses (actually currently wearing one!!) so I love this post!! Definitely need this one. Love how you styled it with that belt bag!!

    Posted 9.16.19 Reply
    • Ah I love it!!! Yes you totally do – comes in the prettiest green as well. Thanks lady 🙂 the belt bag in my newest handbag obsession.

      xo Laura Leigh

      Posted 9.16.19 Reply
  5. Anna English wrote:

    This dress is so cute on you! I love the subtle ruffle sleeve detail.

    Posted 9.16.19 Reply
  6. roxy wrote:

    What a cute dress! It’s so helpful seeing it styled for multiple seasons. I adore the clear convertible crossbody! What a fun bag.

    Posted 9.16.19 Reply
    • Thanks Roxy! So glad you found the post/styling to be helpful 🙂 and thank you – it is my favorite bag right now. Super fun to carry + style!

      xo Laura Leigh

      Posted 9.16.19 Reply
  7. That looks like a super comfy dress. Love the color too. Perfect for the last remaining days for farmer’s market or weekend road trips.

    ❥ tanvii.com

    Posted 9.16.19 Reply
  8. Cathy wrote:

    Love both ways you styled this dress. It looks so cute and versatile!!

    XOXO
    Cathy

    Posted 9.16.19 Reply
  9. Ashley Hargrove wrote:

    I absolutely love this dress!! The details on the sleeves are just so cute! Definitely a perfect dress for summer and even better for Fall!!

    Posted 9.18.19 Reply
  10. Inna wrote:

    Cute dress, I love the styling options!

    Posted 9.18.19 Reply
  11. Greta wrote:

    I love how you styled the dress with the belt bag! Such a fun weekend look.

    Posted 9.19.19 Reply
  12. Comfy midi dresses are the best! I love this one and how you styled it. XO

    Posted 9.19.19 Reply
  13. Laura S wrote:

    Oh my goodness how cute! Such a good transitional piece!

    Posted 9.20.19 Reply
  14. Caitlin wrote:

    This dress looks so comfy! I love how you styled it two ways!

    Posted 9.23.19 Reply