Santa Baby

cute christmas outfits

Whenever Carly and I meet up, we usually just look at each other and laugh. Nine times out of ten, we’re wearing some type of coordinating outfit! Take Wednesday morning, for example. Carly and I met up for breakfast (breakfast dates before work are seriously the best!) at Sarabeth’s and were planning to do a fun shoot with our matching santa hats afterwards before I headed into the office. There were almost tears when we met up in front of The Plaza… Plaid skirts, navy tights, sweaters, monogrammed crossbody bags, navy suede shoes, etc. I think we’re as close to twinning as humanly possible, without actually wearing the same thing. Honestly, the only thing we planned on matching was our hats. (We later realized that she has my Vineyard Vines skirt and I have her J.Crew skirt. #closecall)

I’m so happy with the way the photos turned out… They’re so festive and fun and capture how magical the city is during the holiday season. We look like Santa’s Little Helpers! When I splurged on this Santa Hat a few weeks ago, I didn’t realize how much I would actually wear it. I just loved it so much and knew I had to have it! (Even if just for a dress form decoration in my bedroom!) But I’ve been sporting it on the commute to work, running errands on the weekend, you name it. It’s so cute! It’s currently on sale and then an extra 25% off so if you’ve been lusting after it, nows the time to get it!

PS: If you’re in New York over the holidays, you have to check out the fountain in front of The Plaza! Once the water is drained from the fountain, it’s filled with Fraser Firs. So pretty! The perfect backdrop for festive photos.

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What I’m Wearing…
Kate Spade Santa Hat (only $66 right now with code JINGLE25!)
Theory Camel Coat (on sale!)
525 America Sweater (also available here & here!)
Vineyard Vines Plaid Skirt (old, similar here, here, & here!)
J.Crew Super Opaque Tights
C.Wonder Pumps (old, similar here & here!)
Ralph Lauren Bag
Kate Spade Bow Ring (old, similar here!)
J.Crew Bow Necklace (old, but this one is almost identical and this one is under $8!)
Kate Spade Bauble Necklace (old, similar here & here!)

Carly’s Outfit Details…
Kate Spade Santa Hat
J.Crew Peacoat
J.Crew Sweater
J.Crew Gingham Shirt
J.Crew Vest
J.Crew Skirt (old, similar here)
J.Crew Tights
Jack Rogers Booties (old, similar here)
Bauble Bar Necklace (sold out, similar here)
Gigi New York Bag

Photos by Bekka Palmer


Right now all Kate Spade sale items are an extra 25% off! Here are some of my favorites… (PS: It’s not too late to receive them by Christmas!)

Current Faves

Leave a Comment


  1. 12.19.14

    Beautiful outfits!! Thanks for sharing! The skirts are such a fun staple even after the holidays! 🙂

  2. 12.19.14

    You guys look so cute! I love the plaid

  3. 12.19.14

    You girls are too cute! Loving the plaid and the fun hat:)

    Heidi D.

  4. 12.19.14

    You two are so cute.

  5. 12.19.14
    Courtney said:

    Ya’ll are adorable! I love your skirts! 🙂

  6. 12.20.14
    Natali said:

    You both look so cute and festive! Lovely outfit!

  7. 12.20.14
    Ilia Mura said:

    These outfits are so pretty and festive – definitely Christmas party material

  8. 12.20.14
    Prudence Yeo said:

    Both of you look

  9. 12.20.14
    Prudence Yeo said:

    Both of you look so cute, love your preppy chic outfits!

  10. 12.20.14

    You both look adorable- I love this Preppy Christmas look ! Merry Christmas to you both!

  11. 12.20.14
    Lauren said:

    Haha, my best friend and I do that all the time . You two look very cute. Lovely post!


  12. 12.20.14
    Meagan said:
  13. 12.20.14
    Jeanne said:

    Amazing pics! Such an inspiring post!

  14. 12.20.14
    Ashley said:

    I love this little photo shoot, super cute!

  15. 12.21.14
    Emily said:

    I love this! My best friend and I always do the same thing!

  16. 12.22.14
    Andrea said:

    These photos are too cute Jess! Love the matching outfits…you both have great taste…and now I have an idea what I’m wearing Christmas Day! Merry Christmas!


  17. 12.22.14
    Melissa said:

    Adorable photos!

  18. 12.22.14

    You two are so cute! Love your skirt!

  19. 12.22.14
    Chris said:

    You two look flipping amazing!

  20. 12.22.14

    Lovely coats 🙂

  21. 12.22.14

    Such cute pictures! Love the hats!

    Madison Martine

  22. 12.22.14
    Diana said:

    Your plaid skirt is too darn cute!

    XO Diana

  23. 7.19.16

    What do you think of Hawaiian inspired apparel? I love the look of my man in his Hawaiian shirt and shorts.

  24. 6.14.20
    Preppystateofmind said:

    Great outfits! Love the skirts during the winter time.