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20 Mom-friendly Ways to Wear Skirts & Dresses in the Winter

by Outfit Ideas for Specific Clothing Items, Outfit Ideas: How to Mix & Match Your Clothes

Fight the mom frump in winter too! Here are some outfit ideas for wearing skirts and dresses when it's cold. These looks are #momlife friendly and so cozy for both staying at home or going on errands. Look like a chic mom despite the cold this fall and winter! #winter #fall #moms #outfits #ideas #fashion #style #stayathome

Do you tend to only wear pants and a sweater in the winter? Here are some awesome ways to change it up! Outfits using skirts and dresses can be just as warm and they take the “mom chicness” to another level… without sacrificing comfort!

If you are new to the blog, our purpose here is to give you tips, advice, and style ideas to keep your outfits look cute, classy and in-style, while keeping our focus on mom-friendly. It’s hard enough to keep outfits staying mostly clean throughout our daily life, let alone try and figure out what’s trending or in style for the current season.

The photos below come from members of our community who fearlessly accepted our challenge to style skirts and dresses for fall/winter weather.

Before we get started, though, here are a few tips for styling outfits well.

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Fight the mom frump in winter too! Here are some outfit ideas for wearing skirts and dresses when it's cold. These looks are #momlife friendly and so cozy for both staying at home or going on errands. Look like a chic mom despite the cold this fall and winter! #winter #fall #moms #outfits #ideas #fashion #style #stayathome

Tips For Wearing Skirts & Dresses Without Looking Frumpy

  • Get leggings and tights! For leggings, have a pair of neutral (black or brown) as well as solid color (burgundy, navy, olive) ones. For tights (great when you’re wearing something other than boots) black ones will work with everything!
  • Accessorize! Time to pull out those cute scarves and belts.
  • Layer! To get an skirt or dress to be super cozy and warm, think about base layers + middle layers + top layers. Example:
    • Layer 1: Cami + Denim Skirt
    • Layer 2: Button-Down Shirt + Leggings
    • Layer 3: Cardigan + Boots
  • It all comes down to proportions. Balance flowy pieces with fitted pieces to avoid looking frumpy.
    • Flowy dresses can be worn with belts or structured jackets/cardigan
    • Flowy skirts should be countered with a fitted top. You can do a full or partial tuck for further definition.
    • Mini and knee-length skirts are the easiest to style without looking bulky. Just add tights or leggings and boots for great proportions.

Now onto the outfits!

Dresses in Cold Weather

Credit: Carrie in Frumpy Fighters.

Credit: Carrie

Credit: Carrie in Frumpy Fighters.

Credit: Carrie

Corina, Blog Founder.

Corina, Blog Founder.

Credit: Eileen in Frumpy Fighters.

Credit: Eileen

Skirts In Cold Weather

CONTEST WINNER! Credit: Dana in Frumpy Fighters.

Credit: Dana

Credit: Mary in Frumpy Fighters.

Credit: Mary

Credit: Natalie in Frumpy Fighters.

Credit: Natalie

Credit: Natalie in Frumpy Fighters.

Credit: Natalie

Credit: Natalie in Frumpy Fighters.

Credit: Natalie

Credit: Kathryn in Frumpy Fighters.

Credit: Kathryn

Credit: Marika in Frumpy Fighters.

Credit: Marika

Credit: Shay in Frumpy Fighters.

Credit: Shay

Credit: Abigail in Frumpy Fighters.

Credit: Abigail

Credit: Abigail in Frumpy Fighters.

Credit: Abigail

Credit: Johanna in Frumpy Fighters.

Credit: Johanna

Credit: Carrie in Frumpy Fighters.

Credit: Carrie

Corina, Blog Founder.

Corina, Blog Founder.

Corina, Blog Founder.

Corina, Blog Founder.

Corina, Blog Founder.

Corina, Blog Founder.

Corina, Blog Founder.

Corina, Blog Founder.

Blog Signature - Corina.jpg

Which of these outfits was your favorite? Are you going to give skirts and dresses in the winter a shot?

Pin to Pinterest to Keep This Handy!.jpg
Fight the mom frump in winter too! Here are some outfit ideas for wearing skirts and dresses when it's cold. These looks are #momlife friendly and so cozy for both staying at home or going on errands. Look like a chic mom despite the cold this fall and winter! #winter #fall #moms #outfits #ideas #fashion #style #stayathome