Fall Instagram Roundup

This fall has been one for the books! I’ve gotten to travel to some bucket-list places in New England and saw some of the prettiest foliage of my entire life – plus I got to spend it with some amazing friends and family! In today’s post I’m rounding up all of my Instagram photos from New Hampshire and Vermont. We hit New Hampshire RIGHT at peak foliage and it was honestly so breathtaking – I look back at photos and still have a hard time believing I was actually there! I’m dying to go back again next year. Vermont was also really fun – we stayed at the Equinox Resort again in Manchester (one of my favorite hotels of all time) and I got to spend time with my friends Nichole, Jessica and Jasmine.

I uploaded my Vermont Guide to the Travel Guide section of my blog this week, including all of the info on Equinox Resort!

knit sweater

Topshop sweater // Free People jeans (25% off!) // suede booties // Sole Society hat (sold out), similar HERE // MAC lipstick in “Angel”

Sole Society hat (sold out), similar HERE // Topshop sweater // Paige jeans

baker boy hat // white sweater // suede booties

chevron stich poncho (only $15!!!) // Paige jeans // suede boots // baker boy cap // MAC lipstick in “Angel”

white lace tank // plaid cardigan // Paige jeans // Stuart Weitzman over-the-knee boots, similar but less expensive HERE

buffalo check PJ shorts (only $7!) // white tee // fuzzy socks

my outfit: burgundy sweater // Paige jeans // Stuart Weitzman over-the-knee boots, similar but less expensive HERE

colorblock sweater, found an almost exact dupe HERE for less than $25 // Paige jeans

My outfit: Free People beanie // knit sweater // Paige jeans // Stuart Weitzman over-the-knee boots, similar but less expensive HERE

Jessica’s outfit: cable knit sweater // white pants // Goodnight Macaroon over-the-knee boots

“The Cabin is My Happy Place” pillow // knit socks

Koolaburra Kinslei Tall Boots c/o, also love this pair & this pair // textured turtleneck sweater // buffalo check scarf // black leggings // Winnie’s hoodie

heart sweater // AG jeans // suede booties // Louis Vuitton Neverfull GM handbag

chunky cardigan sweater // “The Cabin is My Happy Place” pillow

If you have any questions about the sizing or fit of any of the items I’m wearing, feel free to leave me a comment below and I’ll respond. 🙂

Oh and stay tuned to Instastories today for a fun video I’ve been working on with my brother!


Leave a Comment


  1. Your New England trips looked so fun!! I hope you’ll get a chance to visit my home state of Maine someday- although I recommend Maine in the summer and not fall, so it’s warm enough to enjoy the beaches 😀

    xoxo A

  2. Your Fall outfits and Fall photos are amazing!!


  3. I have absolutely loved your Instagram content this autumn, Cait! It’s been spot on with the season!

    I hope you have a great Wednesday,

  4. Kathy

    Hi Caitlin! I love your pictures and your blog! Could you please tell me what is the brand and color of the lipstick you are wearing in the picture with the black turtleneck? Thank you! Kathy

  5. Oh wow I love this post, so many cozy fall vibes right here! Thanks for sharing love!
    xx Janine

  6. Awhhhh the dreamiest coziest trip with the best outfits!!! <3
    XO, Katie | http://www.meshkomoments.com

  7. Robin

    This might be a silly question, but how do you avoid getting dark denim stains on your OTK boots and subsequently your white jeans?

  8. Anne Arnold

    Love all these pics Caitlin! I was wondering where your striped dress from your Insta Stories is from? Anne 🙂

  9. Patti

    Great pics! Love the outfits but most of all the beautiful fall scenery!

  10. Very lovely roundup! I’m in love with the Fall! 🙂


  11. Phuong

    Where is the cabin in the last photo?? It looks dreamy!!

    • thank you so much! It was an Airbnb in Woodstock, Vermont 🙂

      • Would you mind sharing the link to that Airbnb? I just searched through all 635 Airbnb rentals and couldn’t find it! 😩🤦🏻‍♀️

  12. Wow this are very beautiful fall pictures, New Hemphire have to visit- I live near Boston.

  13. Lindsey

    Love your style so much! About how much do you weigh… we are the same height so I’m not sure on sizing for some of these items! Thank you 😊

  14. Janet Oloyede

    Absolutely loved this post! You always have the best fall fashion inspiration & year after year it just keeps getting better! Thanks for the round-up!

  15. Obsessed with the fall vibes!! <3


  16. I am so obsessed with your autumnal content!!


    Ellie xx

  17. Liesel

    Hey Caitlin! I know you wear Paige jeans a lot — and I LOVE them! I have seen a few different colors of them and wondered what color you are wearing in the photos with your chevron stitch photos! Thanks! 🙂

  18. Love these images!
    Can’t wait to check out your New Hampshire guide! Trying to get to all 50 states and this state is next on my list.

  19. Elizabeth Bertrand

    Thank you for putting a second price option up for your outfits. I appreciate the research that you do to allow us to be able to afford it!

  20. Marisa B

    Those over the knee boots are perfect for this fall!

  21. Hannah

    Love it!

  22. Christina

    New England is gorgeous, and your hair is to die for!

  23. Megan Himmel

    I am in love and obsessed with your style and especially your fall fashion. I have to say my favorite thing from your fall round up is your new Chloe Bag 😍 only if a girl could afford that Lol.
    I’m really looking forward to your winter looks especially around Christmas and new years!

  24. Kari Gonzalez

    I just ordered the chucky sweater. I love all your beautiful pictures.

  25. OMG, these photos look like an autumn dream!

  26. Taylor

    You have the most perfect hair!

  27. Taylor

    You are what hair dreams are made of! Seriously, hair goals!! 😻

  28. I love that you have been traveling more! Love all these destination spots. Makes me want to cozy up in a cabin somewhere!

  29. Edith Hinojosa

    All these photos are amazing, thank you so much for the life inspiration and showing us that life can be magical, you’re the cutest human on the planet, sending love!♡ love you!

  30. Sabrina

    I am a fan for all things buffalo check and these shorts are no exception! The cozy cabin seems like a little chunk of paradise tucked away from the busy world!
    Also- LOVING Winnie’s hoodie. Such a stylish pup!

  31. Gracie

    Your hair is absolutely gorgeous!!

  32. Kaitlyn

    This post actually made me go out and buy a black fitted turtleneck. I got mine from express tho cuz I like the ribbed material and it’s very stretchy. Also got an ivory one. Don’t you just love a nice comfy fitted turtleneck? I feel like they are so versatile and look good on anyone!

  33. Amanda

    Such a fan of your style. I can’t pick just one!

  34. OMG every picture , i mean every single picture is out of a fairytale book , Absolutely love love love them all .