Reader Request: Cropped Pants for Cool Weather

cropped pants for winter

Reader Ali left this question in a comment:

I’m hesitant to buy all these cute short pants that are in style because I don’t know how to make use of them in the fall or winter, or on cool spring days. I realize it’s still stylish to wear in the winter, but it seems impractical. When would you wear a wool coat and scarf and NOT want to wear socks? So how do you wear those pants AND stay warm?

Ali, I feel ya. As a person living in a climate that regularly includes -30 degree winter days, I am bewildered and frustrated¬†by the current glut of ankle-length and cropped pants. I have a couple of suggestions, but would love more if anyone has ’em!

Pair with ankle boots

This is my go-to solution. Taller ankle boots can typically slide under the hem of cropped pants, and you can wear your thickest, wooliest socks with them if need be. It’s also well within the realm of current chic to have your pant hem and ankle boot top bump up against each other. (Pinterest will back me up on this one.) If you go this route, you can still do socks – just pull them up beyond the pant hem, pick a neutral color, and don’t worry too much if a sliver peeks out.

Go skinny and tuck

This won’t work for dress pants, but anything in the casual levels below is fair game. Hem length ceases to matter if you’re tucking a skinny pant leg into a boot. Boot styles that hit mid-calf and higher will conceal everything, including hems and socks.

Do funky trouser socks with heels

I am not a huge fan of the ankle pant/sock/flat combo, but ankle pants worn with textured trouser socks or tights and wedges or heels can be cute. Like this or this. Thicker socks will make your shoes uncomfortably tight, so think heavy nylons. Speaking of which, you can certainly try nude hose for this same purpose. Both options will offer a bit of coverage, but relatively little protection from real cold.

And I’m out. Got any other advice for Ali (and me)? How do you make your cropped and ankle-length pants work for cooler weather?

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6 Responses to “Reader Request: Cropped Pants for Cool Weather”

  1. fashionforgiants

    This fall I’m going to be all about cropped wide-leg pants, and culottes, with a nylon sock, probably patterned, and menswear-inspired shoes. I’m excited!

  2. Thistle

    Honestly, I own one pair I wear in summer. Cute but seasonally confused over here in the northern Great Lakes region where -30F is a real temperature. I enjoy fashion, but it must first its primary purpose in keeping me warm in the winter and cool in the summer. I will save this look for my southern sisters.

  3. Ruth Slavid

    This isn’t really about how to wear ankle pants, but a great advantage for short legged people like me. I find that Boden sells some great styles as crops as well as full-length trousers. The full-length trousers are always too long – but buy crops in ‘long’ and they fit like a dream as full-length.

    • Dust. Wind. Bun.

      Yes! I was just thinking to myself, “What do I do when cropped pants are in style in the winter? REJOICE that I can buy pants off the rack without needing hemming!” With my 26″ inseam (and the fact that I don’t wear heels for everyday), even petite sizes are often too long, but crops for tall people (or sometimes even ‘regular’ lengths depending on the brand) are just right.

  4. Shelbee on the Edge

    I love all of these suggested looks for crop pants in the winter! I live in Northern New York where we also hit -30 and -40 degree temps in the winter and I have an abundance of ankle length pants in my closet. I am going to try thin pattern socks with ankle wedge boots and some mid calf moto boots with my ankle pants this winter. I also think heavy duty quilted snow boots would look super cute paired with skinny ankle pants and a chunky sweater! Shelbeeontheedge.com