How to Wear Cropped Pants All Year Long

Transitional times between seasons is rough. One day it’s sunny, the next you’re shivering all day long. At least that’s how the weather has been in Seattle lately, which means trying to dress adequately for any weather in between has been rough. Last weekend we even were threatened with the “worst storm to hit in 50 years” that fortunately never materialized. When it comes to transitional dressing, I always love to find ways to wear some of my favorites from different seasons all year long. For me, summer brought a culotte obsession, so now it’s all about figuring out how to wear cropped pants all year long.

Disclosure: Some of the items in this outfit have been provided courtesy of (c/o) the brand. No further compensation was received, and all thoughts are my own. Some links in this post may be affiliate links, and I may earn a small commission if you make a purchase.

What I’m Wearing

Jacket: Blank NYC Morning Suede Jacket in Olive Juice c/o Shopbop (I bought a small for a fitted look, but if you want to layer size up!)
Tee: Lucky Brand (similar or similar)
Pants: Ponte Knit Soho Crops c/o J. Jill (run large, I’m wearing an XS)
Boots: Joré Anna Boots c/o Fred Meyer (similar for less than $75)
Bag: ASOS (similar for under $30)
Rings: Custom White Druzy Ring via Two Cats Artifacts // Gray Druzy via Kendra Scott // Midi Rings via Forever 21
Choker: Charlotte Tie Cord Choker c/o Boohoo

How to Wear Cropped Pants All Year Long

Today I thought I’d share the easiest trick ever to wearing your cropped pants, be it culottes or otherwise, all throughout the cool months. Sure, you could pack them away and opt to wear full-length pants, but why not give yourself even more options? And even better, you already have this item in your closet.

So what’s the big secret? A pair of boots. Yep, it’s really that easy. You can wear your favorite pair of boots under your cropped pants for a chic yet incredibly simple upgrade to your favorite culottes. The boots will keep your legs warm while you’ll still be able to wear your favorite pants. Plus this style trick works for every other type of cropped outfit like your favorite skirts, and everyone knows that boots look incredibly fab with dresses too!

To keep this particular look from looking too stuffy, I opted to pair a graphic tee with my black culottes. I threw on my favorite moto jacket of the season from Blank NYC on the top, and I was out the door and off to West Seattle to check out a house. P.S. Real talk, house hunting sucks, and the Seattle real estate market has lost it’s damn mind. That’s a post for another day I suppose.

So what are some other ways to rock your cropped pants all season long? How about with a pair of ankle boots and socks! You can easily keep your legs and feet nice and toasty while still rocking an on-trend look. You can dress up your pair of culottes with a button up blouse and conservative jacket, or opt to channel your rocker side like I did with this band tee. A lightweight sweater tucked into the front of your cropped pants would work fabulously in this transitional time between fall and winter also.

Any way you style them, I hope you consider giving your cropped pants a new life come chilly fall and winter weather. A pair of boots is a style staple you should already have in your closet, so why not give it a try? I can’t wait to hear how you choose to style your culottes this season!

Do you style some of your favorite pieces from summer all year long? I’d love to hear how you opt to make it work in the comments!