Preppy Pineapples

The first day back from vacay is always a tough one. I just got back last night from spending five nights in Naples, Florida with two of my girlfriends. Talk about a fun-filled trip! It’s back to work today and I’m sure I’ll be feeling that vacation hangover.

I’ve always had a bit of a penchant for anything that’s preppy, printed, and reminds me of paradise. Meet my new pineapple-printed shorts! Pineapples have always made me smile, or at least since 7th grade when I went to Hawaii for the first time. I toured the Dole Plantation and had my fair share of pineapple whip over the course of the trip. I’ve been hooked on the fruit and the shape ever since. Plus, pineapples are a supposed to symbolize hospitality. What’s not to love?!

When I was packing for my trip, these preppy shorts made the cut without any hesitation. I knew that the playful pineapple print would be perfect for a casual dinner on the Gulf!

Gap Jean Jacket (on sale!) | Old Navy Tee (on sale!) c/o | Old Navy Pineapple Shorts (on sale for $10!) c/o | Gap Flats | Gap Sequin Clutch (also comes in a tote version!) | Samantha Faye Pineapple Necklace | Gap Belt (on sale!) | Bauble Bar Bracelet | Urban Outfitters Sunglasses | Sequin Bracelet (available in August!)

Photos: Ellen Landgren (PS – Check out the Facebook page for her two Standard Humans Poodles. They are adorable!)

This post is sponsored by Old Navy. Check out Old Navy’s latest fashion lineup in store or online at

Leave a Comment


  1. 7.30.13
    stephanie commented:

    this is such a cute outfit for summer 😀
    xx Stephanie

  2. 7.30.13
    Jenna commented:

    love those laser-cut flats! such a fun twist on a classic 🙂

  3. 7.30.13
    Kimberly commented:

    Such a cute casual pairing – loving the pineapple print! 🙂

  4. 7.30.13
    Lauren commented:

    Your pineapple shorts are so adorable! Love the clutch too – I’ve been lusting after the tote version all Summer!
    Fizz and Frosting

  5. 7.30.13
    Tara commented:

    Those shorts are so much fun!

  6. 7.30.13
    Rachelle commented:

    Love this preppy look, you look adorable.


  7. 7.30.13
    Stacey commented:

    What fun shorts and for only $10?! They look very J Crew.


    Five Minute Style 

  8. 7.30.13
    Ellen commented:

    I love this outfit so much! Also, you look very tan in these pics!

  9. 7.30.13
    Hannah commented:
  10. 7.30.13
    kileen commented:

    what cute shorts! i love the pineapples.

    cute & little

  11. 7.30.13
    Emily commented:

    Love the shorts…can’t believe they’re from Old Navy! Can you tell me if they fit true to size? The reviews on the site were mixed and I don’t know if I should order my regular size or size up like some reviewers suggested. Thanks 🙂

  12. 7.30.13

    You say preppy and you’ve already won me over 🙂

    Rebecca {at} Preppy Panache

  13. 7.30.13
    allie commented:

    dole whip from the dole plantation is the best thing EVER!! aka pineapples rule.

    allie at

  14. 7.30.13

    those pineapple shorts are awesome! xo

  15. 7.30.13
    Megan commented:

    Those shorts are adorable!


  16. 7.30.13
    Olivia commented:

    Naples is one of my favorite vacation spots! The stretch of stores on 5th Avenue is the best! Those pineapple shorts are so fun. At first glance, I thought they were from J.Crew, but I’m loving that they’re Old Navy and a fraction of the price!

  17. 7.30.13
    Katherine commented:

    I love love love those shorts! Adorable summer outfit.

  18. 7.30.13
    Chelsea commented:

    I love that sparkly clutch Jessica! Your tan looks amazing girl.

    Chelsea & The City

  19. 7.30.13

    Great cas outfit! Love the pineapples!

  20. 7.30.13
    AJ commented:

    I have the flamingo shorts and the lobster shorts! The pineapples are adorable too.


  21. 7.30.13
    Holly commented:

    Love this outfit! Snapped these shorts up today myself.. Adorable!!

  22. 7.30.13
    Kaitlin commented:

    Such a fun pairing, perfect for your vacay!

  23. 7.31.13
    Lubna commented:

    What a lovely outfit. The shorts are such a gorgeous color and I really like the denim jacket.