Changing over your wardrobe for winter always feels like a fresh start. There are old favorites you haven’t worn in forever, and then those go-to pieces that are reliable for winter outfits. Jeans are definitely a winter closet hero, and they can make getting dressed in the winter effortless and fun.
I use affiliate links throughout this blog post, which means I might make a commission if you use my link and then make a purchase. This commission comes at no cost to you.
10 Winter Outfits With Jeans You’ll Feel Chic, Comfortable, and Cozy Wearing
There are lots of outfits below, but here are a few tips and thoughts on styling jeans this winter.
Can You Wear Jeans In The Winter
Jeans are a winter staple. They’re one of the best pieces to style over and over again when it’s cold because they’re so versatile. Plus, they will never go out of style!
How To Wear Jeans In The Winter
Make Sure Your Jeans and Boots Work Together
Boots are always an important part of a winter wardrobe on the east coast, where it gets quite cold. It’s important to make sure your boots and your jeans can be worn together. For example, booties work well with full length jeans, barrel jeans, and straight leg jeans. Jeans with wide legs pair nicely with knee high boots for added warmth, but you can wear wide leg jeans with shorter boots too. You can also tuck your straight leg jeans into your tall boots.
Choose the Right Socks
The right pair of socks is so important for both comfort and style! If you know your bootie will show your sock when you sit down, you probably don’t want bright white athletic socks hanging out – although it’s not a big deal if they’re your go-to socks. If you do want white socks, I love this pair – the ruffle elevates it and adds a fun touch! I’m sharing my favorite socks to wear with boots below.
10 Winter Outfit Ideas With Jeans
Straight Leg Jeans with Booties and A Cozy Top
These straight leg jeans are my most worn jeans ever. They come in so many colors, and they truly are the perfect fit. I love how they work with just about any boot, but I do prefer to wear these with booties. By the way, when I say booties, I don’t necessarily mean ankle boots. I love booties that come up over your ankle – like the pair I’m wearing below – the most! These brown suede boots are so chic and super comfortable!
I also wore a navy wool coat over this outfit for added warmth (you can shop a similar navy coat here), but I’d also wear this with a chocolate brown coat.
Wide Leg Black Jeans and a Brown Crewneck Sweater
These wide leg jeans are super versatile and one of my most worn pairs of jeans this time of the year. They look chic with an oversized sweater, a more fitted sweater, or even a blouse if you want to dress them up. This is my favorite blouse right now. The silk and details instantly elevate your outfit. This blouse comes in lots of different colors, including black, which would be so chic for a monochrome look with these jeans.
Black Jeans and Elegant Navy Cardigan
When it comes to boots, these wide leg jeans work with booties with a heel as well as flat boots. You can easily elevate this look even more by wearing boots with a heel, but I wore these waterproof knee high boots all over Boston for warmth and comfort. I’ve had them for years, and they still look new.
For more ideas on how to style wide leg jeans, click here.
Barrel Jeans And A Cozy Hoodie
Barrel jeans are universally flattering, so give them a try if you’re curious about them. I love how most of them have shorter inseams, so they work well for those of us on the shorter side. They work with boots on those really cold days, and I also love them with flats and sock tights like I’m wearing below.
I recreated my outfit with pieces in stock. These are the same barrel jeans in a different color – I’m wearing a dark navy, and the pair I linked are black. If you’re wondering how to style barrel jeans, check out my blog post all about them.
Wide Leg Jeans With Layers
AGOLDE makes the perfect wide leg jean, and they’re easy to wear with knee high boots or booties throughout the winter. For the colder days, I love to wear this suede jacket underneath a winter coat. You can see that styled below. The suede jacket is actually super easy to layer, especially under my wrap coat or puffer jacket. Speaking of layers, I’m wearing a sleeveless cashmere sweater in this photo. But, this wool turtleneck is my go-to winter layer. I also love to wear these jeans with these cashmere socks and these suede sneakers – that was a recent travel day look, and I was so comfortable wearing it all day (and it was a very long day).
Suede Jacket With A Puffer Coat
This is the same suede jacket but in green. You can see how easy it is to wear under a puffer jacket for extra warmth! And, this jacket looks so chic with straight leg jeans and booties!
Dark Jeans Outfit
Dark denim is a go-to for winter jeans. I love how it’s a little moodier. Dark denim also feels more formal so you can wear it to work or for a night out.
Brown Monochrome Outfit
Brown jeans are the perfect color to wear throughout the winter. I love this sweater because you can wear it by itself on date night or layer it with a t-shirt or lightweight turtleneck for school drop off. Shop my sweater here, my boots here, and similar jeans here. I own the jeans I linked to in black. They’re super flattering.
Blazer With Jeans and Heeled Boots
This is a great work outfit if you work in an office where you can wear jeans. The blazer adds professional polish to your outfit, and it just happens to also be so comfortable. You can wear the blazer with the belt or without the belt, so it’s also versatile.
My boots are similar. My jeans are a different wash, but they’re the same slim wide leg jean! It’s a very flattering style.
Casual Weekend Outfit For Late Winter To Spring
Last but not least, jeans are still a key part of your wardrobe at the end of winter and into spring. Straight leg jeans with an oversized cashmere sweater is the perfect winter to spring transition look. You could wear this with wide leg jeans for a super comfortable outfit, but straight leg jeans better balance out the oversized sweater.
This outfit works for those days when you still want to wear warm pieces, but you can add in loafers with socks and a t-shirt instead of heavy duty winter boots and turtlenecks.
That’s all from me today! Did you find any outfit ideas for how to wear your jean this winter?
