We were talking in our team meeting recently about how a uniform or go-to outfit combination is way more easily achievable than a capsule wardrobe. When you find a base outfit that speaks to you and then you just mix and match a couple of different pieces in for variety it ensures easy dressing and who doesn’t want that right now #amiright.
Currently, my go-to ‘uniform’ for this winter of 2025 consists of moto boots, (slightly) cropped wide leg or barrel leg pants and some kind of sporty piece like a hoodie, beanie or jacket.
I know the trends are baggy, loose and full-length when it comes to jeans right now, but that’s just not that practical for winter. So to keep my cropped pants in rotation, I’ve been wearing them with my moto boots and it turns out that combo is great with the barrel leg pants I adore, too. These boots are tough and perfect for weather and the short pant lengths stay out of the snow, rain and muck.
Similar Hoodie | Similar Pants (so good!) | Boots
Here is the base outfit I started with at first. But, of course, some events call for mixing it up a bit more, so below I’ve swapped in a few different pieces to alter the looks slightly. Having this base look though has made it SO easy to get dressed without thinking much lately. A true godsend.
8 Ways To Style Cropped Jeans In Winter
I struggled with the styling a little, at first, because wait, what? I’m keeping the shoes the same for each look? Typically in a styling article my swaps include shoes, so I switched it up this time. Because, yeah, moto boots are truly one of the best solutions for this gal who lives in the rainy Pacific Northwest and likes to feel badass.
I own them in black and brown so we’re still dealing with a few variables here we can play around with. Let’s dive in and see what clothing swaps work with to mix up the base outfit for different occasions.
For Everyday Errands, Etc.
Similar Denim Jacket (ooh!) | Similar Top | Pants (MR) | Boots | Beanie
What I love here? The longer shirt jacket with the cropped shirt underneath. We’re playing with length and it’s fun and works. The long jacket also plays against the ankle length barrel leg pants, too. It’s like word play, but with clothes. The beanie of course adds that sporty element I’ve been digging so much lately and tops off the ‘uniform.’
Weekend Vibes
Jacket (M) | Jeans (28) | Boots
Ok, cheated slightly here because I loved these snake print boots so much with this outfit…but they DO have a buckle on the side so they’re pretty much a moto boot.
A boxy cropped jacket or top works SO well with a barrel leg jean (and the whole team loves these Moxie Barrel jeans from Free People, trust.) This jacket is such a find at $34, too! I’m loving the almost monochromatic vibe of the jacket and pants for a fresh feel.
Brunch With Besties
Shirt (M) | Similar Pants (or these) | Boots
This gal adores a brunch (along with the rest of Portland) and I always want to feel just a bit leveled up from my everyday outfits when I do get to go. Sometimes I get even more dressed up, but most of the time, here in casual-AF PDX, I just try to do something fun.
My latest go-to top is this Reformation Will shirt, buttoned all-the-way-up, with some kind of jewelry at the neck. I’ve worn this over a variety of pants and it always seems to work. LOVE. It’s my nod to Billie style but with my own take. And…of course, beanie on top.
Almost As Cozy As Sweats
Similar Sweatshirt (or this) | Pants (MR) | Boots | Beanie
These Pilcro Izzie barrel pants are some of my very most worn for the past few months. I wear them almost every other day even though I’m typically someone who likes more variety than that. They’re just so easy, don’t squish my waist and yet don’t look like a lounge pant. They’re perfect.
My black moto boots are Frye, second hand, and I do love them…but I’ve soooo been eyeing up this slightly more gray-ish pair that I think would fit more seamlessly with the rest of my closet (ie. I have more washed black than stark black.)
Profresh-ish
Similar Blazer | Shirt (S) | Pants (tts) | Boots | Hat
In years past I’ve loved a blazer moment and it turns out I still do, but the addition of motorcycle boots AND a baseball cap keep it feeling balanced for my love of tough and sporty pieces. Again I love the longer length blazer here with the cropped pants for some juxtaposition (that keeps the outfits interesting.)
A Solid Travel Outfit
Sweater (M) | Similar Scarf | Jeans (29) | Similar Boots | Bag
This outfit has all the elements I want in a travel look. These Kit jeans by Pilcro are stretchy with a comfortable waist, they won’t drag the floor in the airport or plane thanks to the length, the sweater is soft and cozy but not too hot and a blanket scarf is always a good call for a flight.
And if I’m traveling with boots, those are the shoes I definitely want to wear on the plane instead of packing in my (almost always) already full suitcase.Top it off with a nice big tote bag for your carry-on and voila. I’d wear this on a road trip, too.
Casual Evening Out
Similar Blouse | Pants (tts) | Boots | Beanie
Ok, maybe this is a bit of a stretch but I have been wearing beanies with everything these days. I have these adidas in 3 colors and I’m digging the rose pink with the romantic top. I’d legit wear this and had to include a little sportiness in this look, so here we are. I’d top with a camel coat (forgot to picture.)
Getting dressed in the winter sometimes seems extra hard, so I hope this provides a little bit of helpfulness in that arena when it’s chilly out. I’m curious if anyone else has a go-to uniform this time of year that they love? Let me know! Thanks for being here, y’all.
xo,
L
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