A skirt and sweater combo are always my go-to fall and winter outfit. These looks are so dang cute AND so dang comfy! I swear that skirts and dresses are literally just socially acceptable blankets and I’m here for it.
But – how do you style skirt and sweater outfits in the cold months? I’ve been wearing sweater + skirt outfits for years all over the country (from cold Wisconsin winters to mild California ones) and I have tons of photo inspiration for your own outfit ideas. Keep on scrolling!
How To Style Skirts With Sweaters For Winter And Fall (5 Ideas You’ll Love)
How To Style A Skirt And Sweater In The Cold Months
As a curvy gal, I usually opt for a midi skirt or maxi skirt vs mini skirts. I just find them more comfortable to wear and I prefer the look of them anyway.
The only exception to this rule is when I’m in a colder climate, then I tend to opt for a soft mini skirt paired with tights and ankle boots along with a cozy knit sweater (and usually a beanie and coat!) Or, no tights and tall knee high boots. I just hate jeans so much!! And tights are surprisingly warm. I’ve done winter hikes in Yosemite National Park in a sweater and skirt set.
Anyways, my absolute favorite street style combo is an oversized sweater with a midi skirt. I find this gives me tons of coverage to keep me warm while still being fashionable. I’m a huge believer in re-wearing clothing over and over, so you can see how I’ve styled the same sweaters and skirts over the years in different seasons.
NOTE: these photos were taken over the years and most items I’m wearing aren’t in stock anymore. BUT I hunted the internet to find similar pieces that are in stock so you can shop my outfit ideas!
Above is my go-to long skirt and sweater outfit featuring a sweater from the Aran Islands that I bought while traveling Ireland on my honeymoon. This knit sweater is so dang warm you guys! If you live in a cold climate or are traveling to one, seriously just pull this sweater over any midi or maxi skirt and you’ll be toasty all day.
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The thick pleated midi skirt and sweater outfit combo is always a fun one to pull out around the holidays. There’s just something so festive about pleated skirts – plus they are SO comfy! The stretch waist band is always a godsend during Christmas time when I’m stuffing my face with cookies and wine.
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A mini skirt is a favorite of mine for fall and winter outdoor adventures. As I chatted about above, I think tights are just as warm, if not warmer, than jeans. And I hate wearing jeans! I love the cute look of a mini skirt with boots and a cozy sweater. Feminine yet fits the season. I always opt for a stretchy mini skirt since I hate pinching. Corduroy is always a favorite for cold months, but I do enjoy the look of denim skirts if you wanted to try that with your winter outfits instead.
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Let’s just state the obvious: sequin skirts are SO FREAKING FUN!! They make any ordinary outfit turn into a little party. I mostly see sequin anything dressed up for a night clubbing, but I actually really love pairing my sequin pencil skirt with this pink cropped turtleneck sweater for a cozy look packed with personality. I wore this outfit both while wandering West Hollywood and also to Las Vegas, both in the wintertime.
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When in doubt, shop yourself a black sweater that you love. Black goes with anything – from office approved pencil skirts to bangin’ leather midi skirts for date night. Personally, I’m a lover of color as you can probably tell from all these photos, so my favorite oversized sweater and skirt outfits usually lean towards bright & cheerful. I love reds, whites, oranges and pinks, but you can be as bold or as minimal as you want.
I hope this helps you get inspiration for your own sweater and skirt outfit aesthetic! I’d love to see what you style for yourself – tag me on Instagram @thewhimsysoul so I can hype you up!!
4 comments
THANK YOU FOR THIS POST!!! I always struggle to dress properly for Michigan weather while wearing a skirt in the winter, so this is super helpful:)
Love both your attitude and your looks! You’re stunning! Cheers from a midi-skirt-lover from Brazil:)
Thank you for not being fat phobic. So refreshing to not have to read about how any sort of “non small” body shouldn’t wear most sweaters. God forbid we take up space.
As somebody who cherishes Halloween however dislikes wearing all out outfits, your Halloween pullovers are a flat out gift from heaven. They’re smart and tomfoolery, without being excessively beyond preposterous, making them wonderful for easygoing wear during the Christmas season. Keep up the incredible work!