How To Wear Cropped Jeans And Socks


For the last few years, one question we’ve been getting over and over is all about socks.  Specifically, do we wear socks with cropped jeans in the winter, or do we just suffer bare ankles in the cold?  And if we do wear socks….which ones?

Rest assured, I’m not one to suffer for fashion no matter how cute, so cold ankles are never my jam.  I’ve been rocking socks with crops for a few years now (almost all of my jeans are cropped – you can see a tutorial of how I crop my jeans here)…and I finally sat down to see if there is a method to the jeans-shoes-socks pairing, because it does depend on which shoes/jeans/socks you’re wearing.

However, I was able to come up with a few foolproof combos and strategies, if you’re interested.  The video explains it, but I’ve included a few photos below with links to the products we featured in the video.

Hope this helps!



ps.  The yellow tee and jeans I’m wearing in most of the video are both from J.Crew.  I’m wearing a size S in the tee, and a size 25 in the jeans.

The Foolproof Combo

Vince Newlyn Sneaker (similar here) | black bootie | jeans

leather jacket | puffer coat | LOVE sweater | cozy sweater

earmuffs – similar | hiking socks | black socks | red socks | patterned socks

Other Cropped Jean & Socks Combos That Work

LEFT: turtleneck | sweater | jeans | socks | Vic Matie Derby Shoes

RIGHT: turtleneck | sweater | jeans | socks (similar) | shoes (similar) 

LEFT: leather jacketscarf | jeans | socks | shoes

MIDDLE: fur coat (similar) | shirt (old maje) other option | jeans | socks | shoes | clutch (similar)

RIGHT: hat | mittens (similar) | jacket | jeans | socks | shoes


  1. Thank you, thank you, thank you!!! This was such an awesome January post. Coming from northern Canada means that 10 months of the year bare ankles are not an option!!
    I have 2 pairs of high waisted culottes that I have a difficult time figuring out how to footwear style for cold months…I would appreciate a post on this subject if you were interested in tackling it 🙂

    • I’d love to know that answer too. I bought a couple of pairs and I’m thinking kitten heels work, but I’m in California! Would love to know footwear ideas in general.

    • I would also LOVE to have a tutorial on high waisted culottes for the winter. They’re the most flattering pants in my closet but I have no clue what to when it’s below 60 degrees…

  2. Thanks. Socks add style, no doubt. I always wear black boots. I have at least 8 pairs of black boots. That’s boring. I will now buy some cute socks and be more stylish. 🙂

  3. The striped socks cracked me up, and even funnier was that I was wearing striped socks and cropped jeans while watching the video…going to need to invest in some new socks 😉

  4. I wear really fun socks with my crops and booties! The funner, the better! I’ve worn my husband’s superhero ones (he-and my son, are big fans of fun socks!!), I’ve worn sparkly ones, ones with ribbon or pompom trim…you name it, I’m rocking it! Love this site, I read it compulsively every day! Keep up the great job!

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