Cold Weather

Flannel Dress

When we’re in the dead of winter, I really start to miss my ballet flats and dresses! We’re still quite a ways away from bare legs, but last week we did get lucky with some warmer temperatures. I took it as an opportunity to wear this plaid dress with tights. It’s so funny to me how 45 degrees in January feels so “warm,” especially after single-digit temperatures. 45-degrees in October and I’d be bundled up with boots and scarves, the works!

Carly Heitlinger

Normally trench coats don’t cut it in the winter, but layered with the flannel on this “warm” day, it felt just right. The trench was actually one of my best purchases last year. I retired the one I had had since college because it isn’t as structured. This one looks much more polished.

Ruffle Plaid Dress

The ruffle collar on this dress though 😍

Monogrammed Tote

I have had this monogrammed tote for years. Even though I don’t go into an office anymore, it serves me well when I have meetings in the city or have to pack up a mini “desk” for a coffee shop work session. I tied this gorgeous ski printed scarf on it and it feels like a whole new bag!

J Crew Trench Coat

After December, I put a lot of my plaid away. Anything that’s super red or feels too holiday gets stored. I couldn’t tuck this one away though! The navy and green still works throughout the winter. It has such a fun shape– it’s more of a swing dress. The bow at the waist makes it have a perfect fit. And pockets…. can’t forget the POCKETS!

KJP Dress Carly the Prepster

Trench Coat // Flannel Dress (c/o) // Monogrammed Tote // Tights // Similar Flats 

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This dress is darling! I really love the classic pattern and fit! I’m also ready to pull out the flats and dresses after wearing boots and warmer clothes for a while. Hopefully soon!

Annie Walthall

Hi Carly!! Oh I love this look! Living in Florida this is my kinda winter weight outfit! I would love to see more “work wear” type looks and BAGS. I have really struggled with finding a good work bag that is 1. sturdy 2. doesn’t break the bank and 3. looks nice. I have followed you since college and LOVE your transition to Carly the Prepster since so many of your readers have transitioned with you.


I’m OBSESSED with the KJP flannel dresses. I have it in two colors already, and contemplating getting a third. I love how you have the collar poking out of your coat! so cute!

XO Malinda


Your outfit is super cute and I love the bag! But I did the math and it would cost almost $1070 to recreate your outfit, I wish I had that kind of money to spend but I’m in my mid-twenties and paying off student loans, I can’t afford that. It would be so cool if you put together a list of links for what you wore and a list of “similar items” that are much more affordable in the same post.


Such a cute dress, you styled it amazingly! My favorite piece of clothing were defiantly the shoes I want a pair NOW!


Hi Carly, I read your blog years and years ago and have just re-visited it after giving up my own blog a long time ago (and just re-starting it). It looks amazing! Looking forward to reading more – Europafox.


I love the KJP dress! So classic. I was wondering how you like your J.Crew trench… I have one by LLBean and have been considering a Burberry upgrade. What are your thoughts? Thanks, Carly!