
How to Wear a Skirt in the Dead of Winter
When it comes to dating in the dead of winter, it can be a pretty chilly affair. Also, let’s face it, sometimes you just want to dress up and look cute. That is exactly why I came up with a fool proof plan on how you can wear a skirt in the dead of winter.

Mini skirt in the winter? Never heard of it.
There is a time and a place for mini skirts and winter is not one of them. Yes, it was incredibly cute and flirty in college where we’d run to the bars in our “liquor jackets”. Yes, I know you did it too once a upon a time. Now the time has come to wear adult clothes on -10°F nights. If you want to wear a skirt, maxi and midi skirts should your best friend.
Where I Look For Maxi Skirts
A good maxi skirt is hard to find sometimes. Some of my favorite sustainable places to look for skirts are Amour Vert and Reformation. ASOS isn’t typically a sustainable brand, but they do have options where you can select if you’re looking for something made out of recycled or sustainable materials. Need Supply also carries a few sustainable brands with unique designs. Lastly, I have found some of my favorite skirts thrifting so don’t be afraid to look at your local thrift shop.
Strappy Heels? Forget that. Throw on Your Boots
If you want to lose a few toes, by all means throw on some strappy heels. While they’re adorable, God invested cute boots for a reason. You can take two different paths: over the knee or ankle booties. If it is super cold, I highly recommend you throw on a pair or over the knee boots as well as a pair of fleece leggings. If the weather is bearable, show off your three inches of leg with your ankle booties.
Stay Warm with a Thick Sweater
Last but not least, find a crop sweater you can trust. When you’re wearing a maxi skirt you’ll want to tuck just the front of your sweater into the skirt. This gives your outfit a little bit of depth and helps you not look frumpy.

Other Posts You May Like:
- How to Make Sure a Maxi Dress Doesn’t Swallow You Whole
- What to Wear to a Street Festival
- DIY Thrifted Wrap Skirt (Resizing)
- How to Make a Dress Warm for Date Night
What is your favorite way to wear a skirt in winter? What is your go to outfit for date night? Let me know in the comments down below.
As always,


26 Comments
Secure in Style
That skirt is absolutely gorgeous!!
Terry
https://secureinstyle.blog
PeculiarPorter
Thank you so much Terry!
adi
Such a classic combination dear! You look great in all the pictures.
Adi xx | http://www.fancycorrectitude.com
PeculiarPorter
Thank you so much Adi! So kind!
sundaydahlias
I love wearing knits with skirts in the colder months as well!
https://sundaydahlias.com
PeculiarPorter
Me too! It makes them so cozy!
Becoming His Tapestry
You look beautiful 🙂 Love that skirt and the whole outfit is beautifully paired
PeculiarPorter
Thank you so much!
songsfrommywardrobe
Such a pretty skirt! And so many good tips!
PeculiarPorter
Thank you so much! It’s so comfy (which is my favorite part)!
briannamarielifestyle
Love this outfit ☺️
Brianna | http://briannamarielifestyle.com
PeculiarPorter
Thank you so much Brianna!
Naya
These are such gorgeous photographs of you, Logan! I do not wear skirts enough, they are the definition of femininity and I really like how you styled this look xx
Naya
http://www.nayatilly.com
PeculiarPorter
Thank you so much Naya! I love how feminine skirts look – plus they’re super comfy when they’re the right length.
jenniferpickering22gmailcom
I love that skirt!!
Jennifer
Effortlessly Sophisticated
PeculiarPorter
Thank you!
Brianna Marie
I absolutely love this outfit!!
XO, Brianna
xobrianna.wordpress.com
PeculiarPorter
Thank you so much Brianna!
Alyssa
I recently learned how to wear a skirt during winter when I had a vacation in Japan last December. And I am from a tropical island country so I had so many warmers under my clothes LOL
xx Alyssa | STYLE VANITY
PeculiarPorter
Oh my gosh, I love that! A pair of good leggings, OTK boots, and a long skirt are good match!
Matija
I love this outfit!
Sydney winters don’t get that cold compared to where you live, so I’m lucky I can still wear a mini skirt with thick stockings!!
https://matijascorner.com/
PeculiarPorter
Ahhh, that sounds like such a cute outfit! It’s been a pretty warm winter this year – I’m missing my snow!
Jessica
This looks so cute and cozy! Love it dear, especially the skirt!
Jessica | notjessfashion.com
PeculiarPorter
Thank you so much Jessica!
shelbeeontheedge1
Logan, you are so adorable! I love this maxi skirt. What an amazing print. And ankle boots add a little bit of sass to this fun winter look. I am that girl who wears mini skirts in winter though! Hahaha. Tights are my best friend and over the knee boots. But sometimes it is too cold for even that!
Shelbee
http://www.shelbeeontheedge.com
dousedinpink
These are great tips! I love your skirt and styling!
Jill – Doused in Pink