Ivy League

how to wear a scarf

Back to school season… Can you believe it’s already here?! Even though it’s been quite a few years since the end of summer marked a new school year for me, September always still feels like a fresh start!

preppy back to school outfit, stripe shirt, blazer, scarf, bucket bag, white destroyed jeans, jack rogers sandals

With summer vacations, wedding season, weekends away, Summer Fridays, and trying to spend as much time al fresco as possible, life during the summer always feels a little bit lax. While the weeks fly by, we try to savor the laid-back, lazy days of summer, you know? While I’m definitely not ready to see summer go just yet, I always start to crave getting back into a regular routine. For me, a new season always makes me put my nose back to the grindstone!

navy schoolboy blazer

When I was growing up, back to school shopping was my absolute FAVORITE. I always went a little bit nuts for school supplies (and I still kind of do, I just call them “office supplies” now instead) and shopping for fall clothing always made me crave crisp autumn days wearing boots, blazers, sweaters, and scarves. Whenever I think fall and back-to-school fashion, I can’t help but think of what I imagine a prep school in the Northeast to be like. Gossip Girl, anyone? (Talking the books here, not the show. I’m not going to try to pretend like I haven’t read every single one.) My mind transports me to a cool morning on a tree-lined campus sidewalk, hot coffee in hand with crunchy leaves below my boots. Touches of plaid, classic stripes, rugby sweaters borrowed from the boys, baseball caps, varsity jackets, tweed, and a whole lot of texture.

striped tee shirt, destroyed white jeans

Just like when I was growing up, I can *never* wait until the temperatures drop to start wearing my new fall clothes. (Don’t tell me you don’t feel the same way!) I’m definitely one of those wear now/wear later kinds of people… I recently picked up this striped scarf, bucket bag, ponte knit blazer, and oversized tee at Old Navy and couldn’t wait to wear them out of my closet. While I picture this outfit pairing perfectly with skinny jeans and riding boots, I styled it with destroyed white jeans and my classic sandals for a summer spin. When the weather allows, I’ll tie my scarf around my neck, but until then, it’s great for adding a little pop of color under my collar.

striped tee shirt, navy blazer, preppy striped scarf

ivy wall in the west village, nyc

olive green bucket bag

navy blazer, striped tee, green bucket bag, scarf

ivy covered wall, west village nyc

Get the Look…

Old Navy Blazer
Old Navy Tee
Old Navy Bucket Bag
Old Navy Scarf
Express Jeans (on sale!)
Jack Rogers Sandals
Coach Sunglasses
Michael Kors Watch
Michael Kors Bangle

Created in partnership with Old Navy

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Leave a Comment


  1. 8.10.15
    Kelly said:

    Jess, you’re adorable! And I LOVE the new blog design. It’s amazing! Congrats 🙂

    Kelly | Kelly in the City

  2. 8.10.15

    Girl check out your new site!! Gorgeous! And yes, I love the back to school time of year, even though its been a few years since I was going back to school! haha

    Her Heartland Soul

  3. 8.10.15

    Back to school is my favorite too! And I LOVE the new blog look.

  4. 8.10.15
    Allie said:

    these pictures are so perfect! i love the outfit!

  5. 8.10.15
    Emily said:

    Love this outfit! I feel the same way about “back to school” shopping. I have bought so much fall stuff already and cannot wait to wear it!

    Loving your new site, too! It looks awesome!


  6. 8.10.15

    Your new design looks so amazing! I bet it feels great to have a fresh look 🙂 And as for the fit on that blazer…it looks too good to be true (must have).

  7. 8.10.15
    Meagan said:
  8. 8.10.15
    Jessica said:

    New site design = AMAZEEEEE! I’m the same way, I always crave fall weather so I can break out the sweaters and boots! However, down here in FL we probably won’t get cool weather until like…January…ugh.


  9. 8.10.15
    Mary Kate said:

    I love that blazer and scarf combo! Such a cute outfit especially for the cooler days of summer we have left!

    Mary Kate


  10. 8.10.15
    Merritt said:

    I can TOTALLY picture Blair or Serena wearing this outfit – so tailored and preppy!! Miss you girl!

    The Style Scribe

  11. 8.10.15
    Grace said:

    Ahh! So cute. I never would have thought to do the scarf-under-collar thing..very inspired. This would be SUCH a great airport outfit too — cute, but keeps you warm!

  12. 8.10.15

    Great outfit. I love love love the bag!

    Blonde in Cashmere

  13. 8.10.15
    Kayla D said:

    I am loving the new site design! And, I love your bucket bag!

    Eat Play Dress

  14. 8.11.15
    Natali said:

    Fantastic sandals and a scarf! You look so pretty and elegant in this outfit. 🙂


  15. 8.11.15
    Prudence Yeo said:

    Love the stylish play of stripes in this look and the nautical color palette is so charming! Cool sunglasses too!

    Ray-Ban giveaway now at

  16. 8.11.15
    Nan said:

    Love everything about this outfit! But then again I have never met a stripe I didn’t like!
    Your new site design looks great!
    xo Nan // Simply Elegant Blog

  17. 8.11.15
    Rebecca said:

    The new design looks amazing! Back to School shopping is my favorite! This is my first fall after graduation and it is so sad!


  18. 8.11.15
    Kari said:

    I also loved back to school season- pens, notebooks, binders, new clothes; I just loved it all!

    I’m loving this blazer as I’ve been in the market for a new one. How’s the fit on this though? It’s it stretchy?

    Xo- Kari

  19. 8.11.15
    Ashley said:

    Jess this outfit could not be more perfect for back-to-school style! Stripes are my favorite pattern to wear — so versatile and always chic! Love that bucket bag too, I had to do a double-take when I read it was Old Navy!!


  20. 8.11.15
    Jen said:

    Back to school shopping was always my favorite growing up, too! Old Navy has been killing it lately. Love how you paired that olive bag with the striped scarf 🙂

    xo, Jen

  21. 8.11.15

    Couldn’t agree more – new seasons always make me feel the exact same way. So I’m definitely looking forward to pressing the reset button.

    Josh | The Kentucky Gent

  22. 8.11.15

    I love that bag! Can’t believe it’s Old Navy. The color is sumptuous.


    COFFEESLAG What’s In My Bag

  23. 8.11.15
    Kate said:

    I’m so with you, back to school shopping is the BEST! There’s something just so fascinating about getting brand new notebooks and accessories. And I’m glad I’m not the only one who thinks of Gossip Girl when it comes to fall. Your outfit reminds me of what Serena wore in the first episode.

  24. 8.11.15

    I just bought that tshirt and the bucket bag in black plus a field jacket and plaid vest. Old Navy For The Win!

  25. 8.11.15

    You look great girlie!!

  26. 8.16.15

    I like your simple yet elegant style