Today I will be sharing with you two ways I styled the Simply Pleated Maxi Shirt Dress from Fashions by Ropuddles. At the end of November, Roshanna challenged me to style this white pleated maxi shirt dress. Never one to back down from a style challenge, I agreed.

Styling this piece definitely proved to be a real challenge for me because not only is the dress a maxi length and but it is also unstructured in shape. As you can see, the dress has a lot of volume and because of my strong shoulder line, the dress visually adds weight to my frame.

For reference, I am 5’5 inches tall which is average height but my proportions through the middle are short. The smallest part of my waist sits pretty close to my bust so belting can be pretty tricky. Additionally, my waist to hip shape isn’t really that curved (rounded) so belting there isn’t always the best look for me.
LOOK 1 – Worn as A Dress

This first look is me wearing the dress as intended. To honor my love for structure and contrast, I decided to add a black leather jacket and belt. Although the dress can be worn without the belt, I prefer the belted shape.

Although belting is problematic for the short waisted , I decided that adding a belt was just the way that I wanted to go with this piece. I knew that I could add a second layer over the top of the dress to cover my problematic short waist and straighter hip area. Additionally, buttoning the dress all the way up to the top of the neckline added visual length to my upper torso.


The dress made me think of an extra-long men’s white dress shirt so I used this to inspire the accessories that I chose for both of my looks. For this look I added:

  • An inexpensive black wool fedora with a faux leather accent purchased about 5 years ago from one of the local beaty supply stores
  • A notched black leather blazer style jacket that I bought almost 2 years ago off Ebay for less than $25.
  • A black and white tweed fabric clutch
  • A black leather asymmetrical belt purchased from Amazon
  • A pair of black leather pointy toe high heel Nine West booties purchased two years ago from the end of season clearance sale

LOOK 2 – Worn as A Duster

For my second look I initially wanted to wear the dress with a black bodysuit, but I don’t own one of those AND I didn’t feel like purchasing or making one just for the sake of a blog post. I’ve decided that all the pieces that I feature here on the blog MUST be pieces that I wear in real life.

So instead of a bodysuit, I am wearing a pair of pointe leggings that I already owned and black shaping cami. I absolutely love how this look turned out.


In keeping with the extra-long white dress shirt idea, I kept some of the same accessories as stated above. Because I wanted a more relaxed look this time, I ditched the belt and leather pointy toe booties and I unbuttoned the dress and rolled the sleeves up a bit.

For this look I added:

  • My same black wool fedora
  • My same black and white tweed fabric clutch
  • A pair of black high heel platform suede booties


The best part about wearing a maxi dress like this in the cooler seasons, is the layering potential. Because the fabric isn’t thick, it would be really easy to layer over and under this dress.

In fact, I think I am seeing a 3rd look where I get rid of the black belt and add a pretty red moto jacket with my black ponte jeggings and cami hiding underneath. (Confession – I actually styled this look too but my pictures didn’t turn out.)

The bottom line is that I REALLY love the versatility of this dress and I look forward to finding other ways to style it in the future.

Of the two looks, I can’t really say that I have a favorite this time. I really like them both. Tell me how you would you style this dress? What do you think of the two looks? Let me know down below.

Angie Diwann







1 thought on “One Maxi Shirtdress Styled Two Ways

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