Cropped jeans seem to trip some peeps up when it comes to styling them in the winter.
It’s true that many jeans and shoe combos we love around here show some ankle; it’s a flattering look. But yeah, that pairing gets cold in the winter. Though you’ll still see me doing it in temperate Portland, there are definitely plenty of chilly days where I want everything covered.
Most of my jeans are cropped, so how do I achieve a warmer look I can still love this time of year? With two key pairs of boots that I wear on serious repeat.
1. Tall Ankle Boots In Snake Print + Cropped Jeans
What the eff do we call these higher shaft boots? High-shaft booties just sounds weird to me, so I’m calling them tall ankle boots. Anyway, they keep your ankles covered and warm — I love them. Mine have a bit of a western vibe and a walkable heel. They’re similar to Shana’s favorites she talks about in her recent cropped jeans and boots post.
The only jeans I typically steer clear of with these boots are skinnies. They tend to not lay nicely over the tops of these boots. But I wear lots of straight leg, wide-leg, cropped flare, and boyfriend styles over these puppies. I’m such a fan of cropped jean these days. I hope they stay around a while longer for this shortie. It’s so nice being able to just hack off the bottom of my jeans and not worry about tailoring.
Leather jacket // All Saints Balfern. Favorite ever. Wearing size US 6. So soft and has pockets. I adore the true moto details.
White blouse // This softness is from LOFT, and I love it. I sized up so it’d be a bit flowy. It’s currently on sale!
Jeans (similar) // Mine are old Madewell Slim Boyjeans from years ago, but the similar PAIGE jeans I’ve linked to are SO good. Crop them, and you’ll have a pair very close to mine. Ooh, and these from FRAME look great, as well. If you prefer a blue wash, but no distressing, these Madewell Slim Boyjeans look like a good choice or these FRAME Le Sylvie.
Snake boots // Jeffrey Campbell Kelam boots are selling quickly most places, but I found the exact pair I have on Amazon. Hooray! I find the ivory much easier to wear than the bright white snake. These are comfy and fit TTS. I wear them so, so much.
Scarf // This Everlane scarf has been my cozy go-to all winter long. I’m not even tired of it, which says something this time of year. The color is so good for warming up all my black.
2. Tan Combat Boots + Cropped Jeans
Who knew how badly I needed these boots in my life? I don’t always love black boots, and burgundy and brown weren’t quite what I needed, either. I was so excited to find this tan pair. When I finally got them, it felt like a match made in boot heaven. They’re Frye, so you know they’ll be good forever, and they’re SO comfy. I’ve already worn them a bunch in the last month.
I tend to find tan boots more versatile than black. I have and love my black combat boots especially with my faux leather/coated black jeans. But when it comes to the majority of my other jeans, I love a tan shoe instead. Maybe it’s just something different and unexpected (and if you have followed me on TME at all, you know that’s always my goal). The tan warms up the black denim, and I’m all about an interesting color palette. And speaking of colors…check this gorgeous tie-dyed sweatshirt I just got from Portland artist Anna Joyce (hey, Bday Present To Self). I’ve loved her beautiful creations for years, and this one is major and so pretty…especially with those tan boots. (Y’all want me to wax poetic some more and say tan again?)
Jacket // My Levi’s Sherpa Lined Trucker jacket is one of my very favorites. It’s heavier with the lining, so it’s a great jacket I pull out anytime I’m totes sick of my raincoats. (Read:often) The lining makes it just so cozy to wear and adds a cool outdoorsy vibe I just love.
Sweatshirt // This gorgeousness is from local Portland artist Anna Joyce. I’m such a fan of her beautifully dyed clothing. Check out the robes on her site, too. I have one and love it for warmer weather. And the bedding! OMG.
Jeans // These are the mom jeans I first wore in this post. They work so well with these combat boots. It’s my new everyday combo. They also look great with heels! (Stay tuned for that outfit during this week’s mom jeans style challenge!) I’m wearing the size 30W here, which fits more like a 28/29. They’re perfectly loose in the waist and a little baggy, but not too much. I’m typically a size 27. Topshop does run small, and I kinda prefer mom jeans that aren’t super-duper tight. These have nice stretch, too, though, but don’t stretch out.
Boots // Frye Veronica Combat – These are a really classic combat boot that have been around forever. They’re more easily wearable than a thick lug sole, and can read more classic and tailored than grunge for sure. I love this shade. I have been wearing them with everything from my mom jeans here to all of my coveralls and jumpsuits. I love them with my straight leg and wide-leg cropped jeans so much.
Do you think cropped jeans will continue to be wearable for a while? I sure hope so. I am starting to see some longer lengths these days in straight and bootcut styles, but for now I’m still a solid fan of this ankle-length trend. Here’s to warm ankles! And February birthdays!
Hey, friends. Hop on over to follow me on Instagram @laurajansenstyle to see more of what I’m up to in Portland, Oregon. If you want to shop my current pieces I’m loving and wearing, head over to My Closet!