How to Wear Shorts in Winter

I was doing my obligatory trans-seasonal* wardrobe edit** when I came across my stack of shorts. I hesitated. Do I put them away for winter? Or can I make these work? I’m always up for a challenge, so I decided to try to make them work.

wearing shorts in winter

*I realise it’s mid-winter, but the weather has only just caught up in Brisbane.
** Edit, rather than clean-out, makes it sound so much more fashion-ey and fun. Sorry if it also makes me sound like a complete loser.

If you are up for a challenge, here’s how to pull of shorts in winter without looking too nuts:

  1. Wear shorts with black tights or opaque stockings. So this is the part where your legs actually stay warm. I think black works best, but you can also play with textured stockings and wintery colours. Some fashion-forward kinds might be brave enough to pair their tights with textured socks and/or knee high boots. I’m not that daring. But I LOVE it if you are.
  2. Fabric and length. Pay attention to the fabric and length of your shorts. Denim seems to work well, as does leather. Tweed, brocade and other fabrics that are associated with the cooler season will also place nicely with this trend. Longer shorts definitely look more wintery. Avoid flimsy fabrics and summery prints.
  3. Scream winter on top. To make this trend work, your top half has to be wintery. Think long sleeved shirt or turtle-neck, paired with a scarf, gillet, or jacket or combination thereof.
  4. Boots are your friend.  Boots help balance the look and bring it back into winter territory. I like ankle boots for this look.
  5. Choose a focal point. Either your shorts or your top half will provide the focal point. If your shorts are a print or coloured, keep the rest of the outfit black or neutral. If you are wearing black shorts, you can bring the colour focus back to a jacket or scarf.
  6. Use a scarf. Using a scarf with shorts, particularly denim shorts, ties the whole layering part of this look together. An infinity scarf looks particularly cute.
  7. Keep a winter palette. This look tends to work best with a winter colour palette. Think blacks, camels, browns and jewel tones.
  8. Use texture. By using texture you add interest and the shorts part of the look becomes considered, rather than “I forgot to wash my jeans and this is the best I could do.” You can add texture via your jacket, your stockings or a scarf.
  9. Create a blank canvas. A black pair of shorts over black leggings or stockings creates a blank canvas. It’s actually a great way to wear shorter tops that you normally wouldn’t pair with tights (because tights are not pants). It allows you to be a bit more interesting with your top half.

For more inspiration on how to wear shorts in winter, check out my Pinterest board.


style saturday

Do you like shorts as a winter trend?



23 thoughts on “How to Wear Shorts in Winter

  1. Julie says:

    Love this! Back in the day when I was at uni I use to wear cut off denims with black tights, black polo neck jumper, a tan suede best and hippie beads. I’ve now seen similar outfits 15 years later ?
    Julie recently posted…Street Photography ParisMy Profile

  2. Sammie @ The Annoyed Thyroid says:

    You look ab fab in your winter shorts! I only wear shorts in summer because it’s so darn hot and I have to, I can’t imagine them getting a second innings in winter. That said, I love the idea of thick tights and some ankle boots. I might have to muster up the courage and try it!
    Sammie @ The Annoyed Thyroid recently posted…The Ultimate Rabbit Hole #75My Profile

    • Robyna says:

      I just saw a challenge staring back at me! I know you don’t want those shorts to come back for a while yet – long may winter stay 🙂

  3. kit@lifethroughthehaze says:

    I am yet to see you look terrible in anything! I have a few pairs of shorts but I just don’t think I am nearly cool enough to wear them with tights in winter! I wish I was but I really look like I am trying far too hard!
    kit@lifethroughthehaze recently posted…Am I the only one?My Profile

    • Robyna says:

      I just don’t post the things I look terrible in 😉 It’s all about that confidence thing and not caring too much what others think.

  4. Mackenzie Glanville says:

    I used to totally rock that look, but not sure it would work for me now. But I do love it when people make it work! Right now in Melbourne it is soon freezing I think I need one of those super daggy blanket suits that you plug in lol, oh gosh now that would be so not minxy my hubby would run the other direction! If anyone can look great in shorts it is you!

  5. Kirsty says:

    Love this look. I had forgotten about it and must try again, otherwise the shorts do just sit there. Really loving your style!

  6. Amanda says:

    Great ideas! I love to wear shorts in winter. This article is providing the best info to style with shorts in winters. Thanks and keep sharing.

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