Fit & Flare Made Casual by Jessica Simpson


Prada sunglasses, Jessica Simpson dress, Superga sneakers, Nars lip pencil

A few things: 1) I’m obsessed with this dress. 2) Can we talk about how my legs blend in with my shoes… and the concrete? Someone needs a tan! 3) Sneaks and tennis shoes are the best.


I think I was originally inspired to wear sneakers with flirty dresses from Maegan. This is something she does often and I just love the contrast of casual and sophisticated. My recommendation when doing this would be to wear a dress with a more casual material (read: cotton) but a flirty shape (read: not pencil skirt).


This particular dress is amazing. The shoulders are padded balancing the hips, and the skirt is a full skater but is still long enough to be comfortable. The v-neck is so flattering and the paneled seaming is superb. My only recommendation with this one: don’t eat a huge meal beforehand. My little bump is the result of some yummy home made Chinese!


Thanks so much for reading!

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  • kayleymaybe

    I have 2 kids that I’m constantly chasing, so I totally love the dresses with sneakers in the summer time! Super cute look.

    • thepearshape

      I agree kayley. i’m just loving the trend. so perfect for all day walking!

  • Luci’s Morsels

    I love skater dresses. This one looks so super cute on you!! I love the dress with sneaks look too!

    Luci’s Morsels – fashion. food. frivolity.

    • thepearshape

      Thank you dear! I’m such a fan of this style, both the dress and the pairing 🙂

  • this looks so, so good on you, and laughing about your leg color because oh my gosh, mine is totally the same.


    • thepearshape

      Thanks so much for the kind compliment! And yes, oh my gosh i’ve really got to dip my toe (or whole leg) into the fake tan pool, because it is BAD

  • Debbie Hercock

    love this dress, the colour and shape. looks great on you. That cut is my fave cut too and I’m a pear shape. i think skater dresses suit pears.

  • Super cute! That dress is perfect, especially with the sneaks. 🙂

    • lhaber

      Thanks Emily! I loooove this dress. I’m seriously considering it in white also

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