Have you tried on these shirtdresses from Madewell yet? I grabbed the checked one as soon as it was available and loved it so much, I couldn’t resist the striped version. It’s truly a perfect dress for me right now—loose and comfortable, yet chic and put together. I love that I can run around chasing Jack and feel like I’m wearing my pajamas, but also look like I actually tried. (This is obviously my secret to stylish motherhood).
Anyway, though I didn’t technically style the same shirtdress two ways, they are the exact same cut and fit and only differ in pattern. And the styling works for either dress! I wear the checked dress with the denim shirt around my waist most often, actually, and the olive vest would totally work with the striped dress. Also, for anyone curious about sizing, I sized down one size for this style!