Hello, hello! Welcome to today’s post on styling skirts for the winter. Skirts are a classic option to look sophisticated, and they can add a charm to your outfits that you can’t always get with jeans. Wearing skirts in the winter might seem like a challenge with the weather, but it’s easier than you think to style all types of skirts for the cold! I’ve put together a roundup of tips and outfits for how to wear your favorite skirts in winter.
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Here are a line up of skirts I love!
How To Wear Skirts In Winter
There are lots of outfits below, and you can shop my looks or recreate them from your own closet! One of my favorite ways to wear a skirt in the winter is a midi or maxi skirt with boots. It’s a reliable outfit that you can wear just about anywhere, and you don’t have to worry about staying warm. Speaking of making sure you’re warm, don’t forget cozy socks for extra warmth.
One quick thought about wearing knit skirts and slip skirts – if you’re concerned these skirts might highlight an area you don’t want to highlight, I love to wear an oversized sweater or cardigan as my top. Or, you can wear an oversized button up half tucked to create the illusion of asymmetry – this helps distract your eye and breaks up your outfit. Basically, it takes away the focus from the area you don’t want to be highlighted! I use these dressing tips for myself!
How To Style A Midi Skirt In Winter
Okay, there are so many different types of skirts, so let’s look at a few categories starting with midi skirts.
The Perfect Knit Skirt
If you’ve seen any of my blog posts before, you might have already seen this outfit. I love how classic this look is, which is why it’s still available and even comes in more color options than when I first posted it. This knit skirt is around mid calf or a little lower depending on your height. It’s a really nice length to wear with knee high boots! I save this outfit for special occasions like birthdays, baby showers, or other gatherings that feel special to me. However, I wear the cardigan as a separate with jeans or other skirts.
While I absolutely love stripes, I also love the solid options this skirt and the matching crewneck come in because they have more vertical lines to them. Vertical lines are so helpful when you want to create the illusion of height. If you’re small busted, then the striped crewneck is perfect!
Okay, the cardigan I linked is ever so slightly different than the one I’m wearing, but it’s the same brand. I also linked the crewneck sweater that is an exact match to my skirt. It’s hard to believe it’s back in stock! I was so disappointed it was sold out in my size at the store when I bought this skirt. Anyway, my boots are also similar. My bag is the same, but the leather on mine is pebbled.
Be sure to check out all of the other options it comes in because they’re all stunning! I especially love the olive green skirt, which I would wear with the matching crewneck.
Pleated Skirt Winter Outfit
A pleated skirt with combat boots like I’m wearing below is an edgy but classic outfit you can wear in the winter, spring, and fall. I love the mix of a romantic skirt and edgy boots. The best thing about this outfit – and most of the outfits in this blog post – is that you can wear it to work or on the weekend.
If you’re interested in looking at lines and color analysis like I am, then this outfit is one of my favorite case studies! The sweater and the skirt are both full of vertical lines, which helps me look taller. The sweater is a good option for my skin and hair. While I love black, it can wash me out. So, wearing it as a bottom is the perfect solution because it’s far away from my face!
I’m wearing (and linked to) the same cardigan as the first outfit. Everything is similar except my sunglasses, which are exactly the pair I’m wearing in the photo.
How To Style Long Skirts In Winter
Black Maxi Skirt
Not everyone deals with really cold temperatures and snow, so this cotton black maxi skirt is a great option if you live somewhere with a mild winter. You can wear it with boots like I am, or you can wear it with loafers or ballet flats. However, it does come in wool in the color grey, so there is an option for those of us who need a warmer material in the winter. This denim jacket is perfect for a mild winter too, but it’s also easy to layer over. Click here to see how I layer with the suede version.
A belt fits easily around the waist of this skirt! I’m wearing the petite length in my normal size.
Asymmetric Black Skirt
This black asymmetric skirt is gorgeous, and I love how Madewell styled it with a belt, t-shirt, and sweater. Asymmetric skirts are perfect if you have strong calf muscles and don’t like the way a straight line falls across your calf! I don’t think I’d change much except the specific belt! The belt is also an important piece of this outfit – you can help create the illusion of a longer torso or longer legs by the color belt you choose. For example, if you’d like to create longer legs, go with a black belt to match the belt to your skirt! If you have a short torso and want to make your torso appear longer, go with the lighter belt that matches the top.
How To Style A Slip Skirt In Winter
Suede Blazer With Slip Skirt
A neutral slip skirt will go a long way in your closet from season to season. And, there is definitely a difference between silk and satin when it comes to comfort and quality. Silk is so much more breathable, but if you’re hoping to find an affordable option, satin is your best choice.
Anyway, I love this look for winter because the suede jacket brings in a cozy feel to the outfit. Silk and suede are totally different fabrics, so they really stand out against each other! The suede blazer is perfectly oversized, which makes it a good option to wear with skirts or jeans. It also balances nicely with a slip skirt since slip skirts fit more narrowly than, say, a pleated skirt. I tried this blazer on in store, and it’s just so flattering. You can see a video of how it looks on me here! It’s on my wishlist. I sized down one size!
I love this outfit with the boots, but the loafers will also look really cute. This pair is super comfortable, and a great option if you need to walk a lot when you’re at work. I’ve had several jobs where I was rarely at my desk, so I always wanted to make sure my shoes were comfortable. Anyway, if you choose loafers, I love wearing sock tights or full tights under a skirt in the winter for extra warmth.
Olive Green Slip Skirt Outfit
This cardigan is a cashmere and wool combination, so you know you won’t have any concerns about staying warm! It’s a total dream! This base of this outfit is super versatile, so if you need to elevate it for work, just add a blouse or shell instead of the t-shirt. This outfit also works with this gorgeous olive green knit skirt if you prefer a warmer skirt option. I own this tote bag in a different color, and it’s the perfect bag for work, daily mom life, and everything else. Click here to see it on me.
Brown Slip Skirt Monochrome Outfit
This slip skirt is the perfect chocolate brown. This skirt would be my top pick for a monochrome look in the fall and winter, but you can also wear it in the spring with pastels like pink, yellow, and blue.
How To Style Mini Skirts In Winter
Fun Mini Skirt With Lace
I know there are tons of reasons to wear a mini skirt. But, for me, a mini skirt is a fun option for a night out with friends, a vacation, or brunch! So, that’s how I styled this skirt. I love the lace on this mini skirt because it makes the skirt feel feminine and fun. That detail is also why I styled it with a blazer and loafers that are more tailored. The denim blazer also makes this outfit feel casual but polished. If you’re looking to dress it up, just go with a black blazer! I linked two I’d consider. Tights will help keep you warm!
Did you find a favorite skirt outfit for winter or a new way to approach wearing a skirt in the winter? Let me know what you think in the comments! If you’re looking for ideas to wear dresses when it’s cold, check out my blog post on wearing dresses in winter without feeling frumpy!
