How to Style A Short Skirt for Winter ft. Free People

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How to Style a Short Skirt for Winter
I get a lot of requests for fashion help, especially during the winter season when it is harder to motivate yourself to “get cute” to go out. I recently had a conversation with a girl about how hard it is for her to wear half the items in her closet during the cold months because she has so many cute skirts that she feels like she can’t use. Inspired by her I teamed up with Free People to put together a casual winter style shoot in this cute striped sweater set.
First things first, be smart about wearing a short skirt! There are a few boxes to check before we sport a winter skirt out and about:
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1. Pattern- That cute skirt you’ve got in the back of your closet with flamingos on it? Yeah, it’s probably going to get you some weird looks in January, best save it for June girl. Prints have been in for a couple seasons now, so most girls own a couple print pattern skirts. Be cautious with a print, I would stay away from anything floral or with anything nautical. What ARE we looking for in a cold weather pattern? Of course a fall plaid will convert well to winter wear. Stripes or dots are staples that can be winter style friendly also.
2. Material- This one is a common sense, if your legs are going to be cold it’s a no go. (From one person who is always cold to another, don’t shoot yourself in the foot). This set is a heavier sweater knit, and for December through March that works wonders. You’ll want to stay away from lighter blends and anything thin or flowy.
3. Color- Pastels and “Easter colors” are going to be your unwanted items in this category, save that yellow sundress girl, just a few more months ‘til April. I love neutrals and wearing a grey or white will allow you freedom of color choice in your coat or jacket. I fell in love with this short skirt and sweater set because the colorway feels so “wintery”. Deep blues and dark reds are colors are also your winter friends because they contrast with lighter winter skin and give you a “China Doll” look.
***One final free tip! If you’re still digging the “60’s bohemia” look that blew up last year then I suggest a shorter skirt. To add a little length to a shorter skirt try an over-the-knee-boot.***
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Sweater Set c/o Free People
Over the Knee Boots




  1. you are such a babe! love that dress!!!

  2. I love that two piece outfit! so cute! xx Annette

  3. This is such a cute look!! I am obsessed with it! xx

  4. Those boots are amazingggg. Rocking it girl! Love this look.

  5. Love this set so cute!!


  6. I absolutely love the print of this look and thought your tips were on-point! Great post!

    xo, Sara

  7. I love wearing mini skirts with over-the-knee boots in winter! Such a cute look.
    XO Amanda |

  8. Love it! OTK boots and tights basically make anything winter appropriate haha! I do think, though, that a lot of times you might be able to make a lace or silky dress (something more spring) work if you add a chunky knit or an opposing, cozy texture to it! That's one of my fave styling tricks. Love this post! xx


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