Hiding Under a Hat

Well here it is, guys. This is basically my equivalent of wearing pajamas in public. It’s as basic as can be, but we all have those days where casual is going to have it cut it. When I’m too lazy to do my hair, I’m almost always in a baseball hat. Add a relaxed shirt, comfy jeans, and a pair of sneakers and you’ve got yourself one low-key look. I opted for this easy way out when I was last in Chicago for a day of over-indulging with my friends from college — shopping, eating, and day drinking. #My3FavoriteThings 😉

Vineyard Vines Plaid Shirt (similar) | rag & bone JeansSoludos Lace-Up Sneakers | Michael Kors Watch | Capwell + Co Ring  & Bracelet | C.Wonder Cuff | Yankees Hat | Karen Walker Sunglasses

Photos by Ellen

Leave a Comment


  1. 1.15.14

    Great look! Chic, but cozy!


  2. 1.15.14
    Rachelle commented:

    cute laid back look, love the sneakers.


  3. 1.15.14
    Kimberly commented:

    Okay, this is adorable and perfect – I know what I’ll be wearing this weekend 🙂


  4. 1.15.14
    Kristin Waldman commented:

    Your sneakers are super cute and you make a casual outfit look chic.

  5. 1.15.14
    Meagan commented:

    Love the sneakers!

  6. 1.15.14
    Heidi commented:

    Your version of casual is much more put together than my version. Were you able to get away with a Yankees hat in Chicago without getting crap from anyone?


  7. 1.15.14

    Love that shirt!
    That is the kind of look that I wear when I’m in a rush!

    Love Sara

  8. 1.15.14

    I’m a sucker for a baseball cap, this is too cute!

    Cathy, your Poor Little It Girl

  9. 1.15.14
    Courtney commented:

    Love this casual look! 🙂 You look comfy and still put together.


  10. 1.15.14
    Jen commented:

    You can definitely pull off the hat + sunglasses look! I am a repeat offender of throwing a hat and sunglasses on during the weekend when putting makeup on and doing my hair just seems like too much effort to run to Target.

    ^talking about the running shoe trend on the blog today

  11. 1.15.14
    Michele commented:

    EXCELLENT hat choice. Go Yankees!
    -Michele 🙂

  12. 1.15.14
    Chelsea commented:

    Gotta love a cute baseball cap… you look adorable Jessica!

    Chelsea & The City

  13. 1.15.14
    Ally commented:

    Casual yet still soo so cute! Love those soludos sneaks!


  14. 1.15.14
    Kayla commented:

    You look adorable in your pajamas out in public! Love it!


  15. 1.15.14
    Ashley J commented:

    Haha, day drinking. We would be such good drinking buddies:)

  16. 1.15.14
    Kristi commented:

    Adorably polished casual look – I love it!

  17. 1.15.14
    Code Overdressed commented:

    Absolutely cute! You rock the Yankees cap, oh and those sneakers are so so cute! Shopping, eating and sleeping those are my #My3FavoriteThings!

    Cee. ♥
    Code Overdressed

  18. 1.15.14
    Ellen commented:

    Your photographer #killedit

  19. 1.15.14
    Agi commented:

    Cute outfit!!!!!!!



  20. 1.15.14
    Rose commented:

    Ummm I LOVE those shoes!!

  21. 1.15.14
    Sorcha commented:

    It’s a great look, much better than ACTUAL pyjamas in public which I may have done once or twice in dire situations.

    Sorcha x Bright Field Notes

  22. 1.15.14

    love this look but your hair definitely looked way too pretty to be under that cap! love that plaid shirt – may need to pull a copy cat on this ‘fit.

  23. 1.15.14

    This is the cutest! I love casual and comfortable- perfect for shopping, eating and day drinking! Those are 3 of my favorite things too!! The best 🙂
    lauren at http://www.lakeshorelady.com

  24. 1.15.14

    adorable! this is totally very similar to my everyday outfits! xo


  25. 1.16.14
    Vanessa Swift commented:

    Stumbled on your blog, adoring it! Perfect casual look.

    Cheers, VS

  26. 1.18.14
    cait commented:

    A Yankees hat in Chicago?! You’re a brave girl.

  27. 1.18.14
    AJ commented:

    This is what I would wear every day if I could! Love seeing you in a relaxed Saturday look.