Cold Weather

Outfits to Recreate

I’m so boring when it comes to getting dressed in the wintertime. Summer is so easy! Pick out a cute dress, throw on my favorite sandals, grab your go-to bag. Done. Winter? There’s the temperature to consider, what shoes to wear, matching a coat to your outfit, dealing with tights (I hate it), layering so you’re warm outside but don’t suffocate indoors. Not so easy.
With the weather cooling off and now that I’m in Connecticut working from home most days, I’ve found myself in a serious sweater+jeans rut. With that… I’m turning back to some of my older posts to get re-inspired.

(Also, this was such a good exercise for me. I’ve been feeling a little less than confident about my “style” lately. I know I like to dress comfortably and I have a lot of favorites in my closet, a lot I’ve had for years and years. I think I found myself comparing myself to everyone on Instagram and felt like I needed $800 over the knee boots, a super fancy handbag, and a wide-brimmed hat. But… they’re not me. At all. I love that the outfits I fall back on are things I truly feel comfortable in and 100% myself in. And I really like that I get a ton of use out of my favorite pieces– they’re not collecting dust in my closet!)

Original Post // I splurged on this scarf and it was honestly one of the best purchases I made last year. It’s super cozy and soft. While I wear it frequently, it’s especially great for traveling because it goes with everything and can double as a little blanket on planes and trains.

Original Post // Definitely one of my favorite holiday looks for the year. I have a soft spot for LBDs (my closet is living proof of it) and this one was no exception. Paring it with an oversized, major statement scarf was just enough outside of my comfort zone. It was the red heels though that truly were the best purchase. I’ve gotten so much use out of them and they’re incredibly comfortable as far as heels are concerned. 

Original Post // I found the cocoon coat on a major markdown and have since worn it what has to be hundreds of times. It’s my go-to coat and apparently the go-to coat of most of Manhattan. You couldn’t stand on the subway platform last year without seeing a handful of them. For good reason though; the coat is universally flattering, comes in great colors, and can be dressed up and down. (A version is also available at J. Crew Factory for much less.)

Original Post // While the scarf I got last year is sold out, there’s another equally cute (majorly affordable) version out right now. Feels like cashmere without the cashmere price tag. 

Original Post // My motto for the colder months is apparently “when in doubt wear a vest.” When I first bought the vest, I wasn’t sure how often I’d wear it. It’s probably embarrassing how often I reach for it, but I LOVE it. It breaks up the typical jeans/sweater look and can change the whole look of an outfit with very minimal effort. (Another version is available here for less too.)

Original Post // Although this looks like it’s featuring the cape, I really love the turtleneck. (Quick note, I’m obsessed with the cape but it really takes the right outfit, handbag, and weather to pull it off!) Turtlenecks can be hit or miss, but if the material is right, it’s the perfect way to layer in the winter. At least I think so! I love the way it looks under coats and you don’t have to wear a scarf or anything. I just purchased this one to add to my collection and it’s the softest thing in the world.

Original Post // Another staple in my winter closet is white corduroys. They’re a smidge more wintery than white jeans.

Original Post // Although my obsession with ski sweaters is going strong, adding pom pom beanies to an outfit is one of my favorite winter tricks. Easiest way to stay warm and look extra cute (even with simpler outfits!)

Original Post // My FAVORITE way to layer? A tuxedo shirt under cable knit sweaters. I do this at least once a week… Seriously though. The tuxedo shirt is the right weight for layering and the “collar” looks amazing under a sweater.

Original Post // I just love a good plaid pant. I got this year’s version already and intend on wearing them as much as possible!

Original Post // This faux fur vest turned into my favorite “glam” accessory. Forever 21 has the best selection of them that I’ve seen this year. 

What are your winter staples?

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Phyllis Lee

I love all of these outfits! I definitely feel you on the struggle of balancing your own style and what's trending. And you're right that we don't need $800 boots and THE handbag to look great. I love your outfits in this post though. They are adorable and so feminine!

Phyllis |


Carly this is probably one of my favourite posts of yours. Thanks for the inspiration, and remember that while you are lusting after other people's wardrobes there are some of us lusting after yours!

Audrey Coyne

Love this post! The looks are so great and I can completely relate. I have a majorly downsized wardrobe and re-wear my favorite looks countless times, and wouldn't have it any other way. 🙂

xxo Audrey


Hi, Carly! I’m an avid reader of TCP, and I’m currently going through your “cold weather” category posts trying to figure out the best cold weather necessities. I’m moving from CA to VA for law school, and plan to buy as I need, but want to get a few basics while they’re marked down in the summer!