Floral Midi Skirt with Button Down And Sweater Vest

How To Wear A Midi Skirt In Winter

It’s the dead of winter and you’re cold.

But that cute floral midi skirt is staring at you whispering ”wear me…” every time you walk into your closet.

Sigh.

When you get to that point in winter where the jeans, boots, & sweater looks are no longer exciting it can be a bit depressing.

But the bright warm side of your closet doesn’t have to be in hibernation, you can make it work for winter too.

Seriously!

Today we are going to talk about how to wear a midi skirt in the winter, but you can wear lots of other ”summer” items in the winter as well.

High waisted floral midi skirt

Where Should Midi Skirts Fall?

Midi skirts are universally flattering and my favorite skirt length!

The important things to pay attention to with midi skirts is the length. Midi skirts are the most flattering when they hit about 2-3 inches below the knees.

Any shorter than that and it’s knee length instead of midi. Any longer and it hits that weird spot in between midi length & ankle length that isn’t my favorite personally.

I am 5’ 6 1/2” (yes the 1/2” is important lol) and the length of the floral midi skirt in the photos is about 27” from the top of the waistband to the bottom of the hem.

I made a floral midi skirt for my bestie, who is tall, blonde, & gorgeous and I shortened the length by 2 inches to fit better on her 5’ 9” frame. It turned out beautifully!

Shopping Tip: Before buying that cute midi skirt you’ve been eyeing, whip out the measuring tape and measure from where you want the waistband to sit down to where you want the bottom of the skirt to be – preferably around 1-2 inches below your knee.

Check the measurements of the skirt you want before buying to make sure it matches what you need.

If you love it and it’s longer than you need (and they won’t adjust the length for you) then you can always take it to a tailor or the cleaners and have them alter it for you.

Just remember: making things shorter is a breeze but it’s impossible to make them longer.


Floral circle skirt with black top

What Tops Do You Wear With A Midi Skirt?

Midi skirts typically are high-waisted skirts, meaning they sit high up on the smallest part of your waist.

The #1 most important thing you can do with ANY top you wear with your midi skirt is to tuck it in!

Midi skirts rock at giving you a beautifully defined waist and by tucking your top, you’ll make sure that beautiful shape of yours doesn’t get lost.

If you don’t want to tuck the whole thing in, at least tuck in the front or some part of the front – whatever allows a glimpse at that waistline. Trust me, it’s waaay more flattering to wear a top with a midi skirt like this!


Floral Midi Skirt with Button Down And Sweater Vest

How Do You Style A Midi In The Winter?

The first step to styling a midi in winter is to think in layers.

Instead of wearing just one layer, try adding a second one. Instead of short sleeve or sleeveless tops try long sleeve versions.

This is a great time to break out those cute cropped jackets & vests you have in the back of your closet.

Workwear

Try layering a classic white button down shirt with a cropped sweater vest for a chic workwear look.

Or swap out the button down for a satin cami or blouse with a cropped blazer.

Or wear that cute sweater you love as long as you tuck it in.

It’s all about the tuck.

Weekend Wear

For the weekend, or any time really, try pairing a sleeveless top (tucked in of course) with a fun cropped jacket.

Or one of my favorite pairings is a graphic tee with a cropped moto jacket

Or keep it simple and just wear a neutral long sleeve v neck shirt!

Top options are endless as long as you remember


Floral Midi Skirt with cropped jacket and boots

What Footwear Goes With A Midi Skirt?

Figuring out what shoes to wear with a midi skirt can be intimidating but really the options are endless!

Heels

Heels always look great with a midi skirt in winter & with just about anything really! They elongate your legs and are super fashionable making them perfect for the professional world.

Wearing heels can give you a confidence boost too!

Try some always chic black heels with an ankle strap and closed toe for those colder months. Or stick to the classic closed toe pumps, you can never go wrong with those!

Knee High Boots

Another classic pairing with a midi skirt is a tall knee high boot.

Knee high of my favorite things to wear in winter, and you can wear them with your midi skirts too!

Try taking the top & cropped jacket pairing from earlier and adding some knee high boots. You can find tons of midi skirt & knee high boot outfits ideas on Pinterest.

Sneakers

Another cute combo is pairing your cute midi skirt with some trendy sneakers. Throw on a tank top & a jean jacket and you are ready for some grocery shopping in style. Even when you’re dragging the kids with you.

I love a good fashionable yet practical outfit!

If you don’t have the money to shell out for those still cute golden goose sneakers, it’s ok. There are a ton of knock-offs out there that are just as cute.


Floral midi skirt with sleeveless top and sneakers

Conclusion: How To Wear A Midi Skirt In The Winter

Hopefully now you see that yes you can wear a midi skirt in the winter!

Midi skirts are one of the most versatile skirts and can be worn during any season by just adjusting the type of tops and the type of footwear you choose.

To recap:

  • Always tuck in your top when wearing a midi skirt
  • Try long sleeve tops instead of sleeveless or short sleeves
  • Think in layers – White button shirt + sweater vest or cute top + cropped jacket, etc.
  • Knee high boots work well with midi skirts – go for a pointed or almond toe to lengthen your legs
  • Heels are always a good option but boots & sneakers can look cute too

Hopefully you feel inspired to take that cute midi skirt out of hibernation and try out some new outfit combinations.

If you have any other outfit ideas for wearing midi skirts in the winter let me know in the comments!

Until next time beautiful!

P.S. If you loved this floral midi skirt then check out my Etsy shop!

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