Easy winter outfits with skirts

It’s not *quite* freezing yet so I’m enjoying some in-between dressing right now, and I’ve made quite a few outfits with midi skirts and sweaters this month! This is an easy winter outfit idea for work and it has definitely become a habit of mine. Here are four midi skirt and sweater combos I’ve been enjoying:

Sweaters and midi skirts

Oops, am I a creature of habit or what? As I was laying out outfits for the week I recognized a bit of a pattern in color choices and silhouettes. Half of me thinks I should “really branch out” but every time I do whatever cool, different thing I buy just ends up hanging out alone in my closet. I’m embracing formulas for getting dressed. I have to get outside faster, I only have like 7 hours of daylight to enjoy now 😦 Here are some ways I’ve worn midi skirts lately:

All white

I love this outfit. And yes, I did tuck my sweater into my bra for this look. I can extend the longevity of this outfit a bit by swapping in some warmer brown boots. I haven’t found any tights I like with this one yet, though.

Sweater (similar)

Skirt (similar)

Shoes (similar)


I’ve punched an extra hole in a few belts recently (there is a real tool for this but I, unscientifically, have been hammering a nail through the belt. I only recommend this if all your belts are old, cheap, and otherwise thrifted) to give waist definition to my skirts. I like that this allowed me to do a half tuck here.

Sweater ($30 off of Brass orders here!)

Skirt (thrifted, similar)

Belt (old, similar)


With a blazer

I am surprised by how much I liked this oversized blazer with my leopard midi skirt! I think that because the skirt has a slimmer cut it worked better than it would with an a-line skirt. I felt like a boss all day in this.

Blazer (similar)



Chic undertaker

Just kidding. I don’t know if I really liked this outfit, though. This thrifted sweater is so cooool yet I am intimidated by the sleeves. Maybe with a non-patterned skirt I would be more comfortable? Please advise

Sweater (thrifted, similar)

Skirt (thrifted, similar)


And just for fun: I asked on Instagram this week where people got their favorite sweaters from. The results were all over the place! The most common recommendation was Everlane, but other good answers included:

  • The men’s department
  • Thrifted, 40-year old LL Bean
  • My aunt bought it off QVC

Hope you are staying cozy.

This post contains affiliate links that may generate commission for the author. 

4 thoughts on “Easy winter outfits with skirts”

  1. My favourite sweaters are from the Gap. They’re washable merino. Since I’m only shopping sustainably now it’s a bit more of a challenge because I only allow myself to buy them second hand!


  2. I love every single one of these outfits. And I’ve never figured out how to pair sweaters and skirts even though I love wearing both, so this is so helpful!


    1. Thank you! It’s hard to figure out how to get waist definition for sure–I don’t know how all these cool street style people pull off wearing a giant sweater untucked over a long skirt!!


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