5 Bold Winter Hats You Should Be Wearing


You know this story:

Snow is lightly falling, there’s a chill in the air, and you need something to cover your head before heading out the door to enjoy the day.

So you dive into your collection of beloved beanies, some are a little faded and there’s the one that lost it’s pompom ages ago. You tend to buy a new one each year, and yet never get rid of any of the old ones. For sentimental value, you suppose.

You grab one of the many black ones, slip it on and head out the door.

Everything is fine – you’re toasty warm – and yet looking around, you can’t help but feel a bit like one dull grey fish in the sea of black and grey beanies filling the streets.

You can feel your inner creative muse sighing in exasperation, she’s counting down the days to warmer weather when she can come out and play in your wardrobe again.

Another day, another black beanie…but that’s winter right?


You may feel that once winter hits your ability to be creative goes into hibernation mode, but there are ways to express yourself even when temperatures drop.

I, for one, have become a huge advocate for hats. All varieties from cloches to oversized fedoras to vintage toppers.

I’ve found they are the perfect way to add a zing of personality to your winter wear.

And yes, they’ll still keep you warm.

Take a peek at my winter hat collection and see 5 different styles you can rock in place of your standby beanie this season.



The perfect fall hat that you can continue to rock all winter long. This is the hat that gets the most wear out of all of them, only second to the beanie. You’ve seen it in several outfit posts, most recently – here, here, oh and here.



This bell shaped hat that came into popularity during the Roaring Twenties. Wear this to add a vintage touch to your ensemble.



This hat is traditionally made out of straw for the summertime, but you can find wool options too. The extra wide brim is perfect for keeping falling snow out of your eyes.



For when you’re feeling dandy, a bowler hat is a fun and unexpected twist to any modern day look.



An odd name, but a fun hat nonetheless. If a fedora and a cloche had a baby, this would be it.

Any one of these would be a lively addition to your closet. And you can find them anywhere! From hat boutiques to vintage spots or even budget friendly department stores – half of my hats were purchased from Target!

Why be one dull grey fish in a sea of black beanies, when you could be a brightly colored reef fish with a cloche or mushroom hat?

Or in other words – don’t be afraid to get creative and stand out from the crowd this winter.

Your muse will thank you.

hats off to you,


4 Responses to 5 Bold Winter Hats You Should Be Wearing

  1. Cute hat collection. Now that my fro is smaller ( yea! hair cut) I can actually wear a lot of these styles. What type of coat style works Cloche? I find that one hard to pull off at times.

    • Thanks Jenni! I usually wear a peacoat with my cloche, I think they look great together and it adds to the vintage look. You could also try a coat with an a-line cut, it’s more feminine which pairs perfectly with a cloche. Hope that helps!