15 Pretty, Hat Friendly Winter Hairstyles

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Few things are worse in the winter than styling your hair perfectly and then having to put a hat on top so that it’s all messed up or squished down flat by the time you get to work. Half the hairstyles we liked to wear most hardly even fit under a hat, but it’s too cold where we live to go without one and still survive the commute to work! Over the years, we’ve learned that they key to successful hair and hat harmony is working the hat into your look, rather than thinking about your hair separately and then having to try and stick the hat on top and hope for the best.

Check out these 15 adorable hat-friendly hairstyles for you to try rocking with your favourite warm toque or beanie this fall and winter!

1. Three twisted buns

Cup of Jo suggests wearing your hair tied up into three adorable little knotted buns to keep it from bothering your neck and face when you put your hat on. Because styles that sit high on your head don’t really work with hats, however, they also suggest wearing those three little buns down low, by the nape of your neck. They’ll stick out at the back just below the line of the hat where people will be able to peep how cute they are.

2. Single rope bun

Do you like the idea of a cute, twisted low bun, but your hair is very thin and doing three will just look silly because they’ll be so small? Then try just doing one instead! Cup of Jo suggests doing a rope bun, which involves making a low ponytail, twisting the hair in the elastic around like a tight rope, and then wrapping it around the base of the ponytail into a bun. It’ll sit low under your hat like a cute little cinnamon twist.

3. Friendship fishtail braid

Braids are always a great way to beat the winter hat dilemma because they leave your crown free for hat wearing but they still look cut sticking out the bottom, whether you wear them to the side, at the back, or on either side hanging down. Just in case you want to jazz things up to make up for covering most of your hair, here’s a unique style from A Beautiful Mess! Create a fishtail braid hanging down to one side but, instead of using just your hair, incorporate thin coloured yarn or string in place of some strands so that a bit of colour weaves through your braid. It’ll look like a friendship bracelet!

4. Triple twisted ponytail

Low ponytails will always work with hats, but they’re not always the most exciting look. You can, however, make many different little adjustments to them to create a look that still works but is a bit more visually pleasing! We love this triple twist ponytail style from Twist Me Pretty because they lovely twisted part will sit just right below your hat when you have it on or at least sit out of the way until you take it off to reveal the pretty detail.

5. Diagonal braids

Did we mention that braids are a life saver when it comes to winter head gear? If not, then we should have, because it’s only the truth! Perhaps you’re looking for something cute to go alone with a knitted headband that covers your ears? This might take a little more thought because the headband has to fit over, but you’ll still be able to see your hair at the top. That’s where French and Dutch braiding styles save the day! Try this adorable diagonal braid idea from Refinery 29. People will be able to see the cute angled detail at the back where your headband cuts off.

6. Messy fishtails

Are you a big fan of the pigtail look when it comes to wearing winter hats and toques? That’s a classic that everyone, including us, appreciates. Sometimes, however, it’s nice to switch things up and put unique little twists on the classic look. Brit + Co. has that all figured out! They suggest doing messy fishtails by creating the braid and then loosening some of the strands to pull the hair out for a bulkier look.

7. “Twisted sister”

Perhaps you’re looking for a hair style that looks amazing both under and outside of the hat? You want it to fit underneath the hat but you want it to look glamorous when you take it off too. The Beauty Department suggests creating a pretty twist look that falls somewhere between a loose braid on top and a messy twisted bun on the bottom. The style is a perfect example of balance, with parts that are sleek and smooth on top for the hat and parts that are body filled and eye catching where the hair sticks out from underneath.

8. Low braided bun

Are you in love with all these different low bun ideas but they’re still just missing a little something in your opinion? Let us refer again to our love for braids! Braiding the bun adds a little bit of texture and visual appeal and shows that you made an effort on your hair despite knowing that you were about to cover it, at least for a while. Check out how simple the style is to do on A Beautiful Mess!

9. Knotted ponytail

Usually finding knots in your hair is a bad thing, but in this case we feel a little bit differently! In fact, we’re totally in love with the style. It sits low enough to show under a hat and also to not interfere with your hat while you’re wearing it. Beyond that, the knots have a cute, whimsical look that’s almost kawaii, if you ask us. See how they’re made on Brit + Co..

10. Front baby braid

Do you like to wear your toque or beanie a little further back on your head so that you can still keep some hair out the front or let your bangs frame your face? Well, according to Jillian Harris you can get fancy despite your hat at the front of your hair as well! We love this tiny braided look that crosses from one temple, along the top of your head by your front hairline, and down the other side in a long braid.

11. Segmented pigtails

Are you still hooked on the idea of pigtails with your hat, but you’re not past the idea of making them a little more unique than just ponytails or braids? Then you need to check out this adorable segmented style from Brit + Co.! It’s simple- use tiny elastics wrapped periodically around each pigtail to make little sections of hair. Try pulling the hair in each section looser so they look like cute bunches rather than just random elastics.

12. Wavy to the side

Do you prefer wearing your hair down than pinning and tying and twisting it back? That can work with winter hats too! In fact, most people we know simply opt to wear their hair down rather than up with a hat, but it’s nice to make things look a little more special than just the way it dries. We love Brit + Co.‘s suggestion for sweeping it all to one side and curling it into lovely loose curls that will fall onto your shoulder, cascading out the bottom of your toque.

13. Gibson roll

Have you ever heard of the Gibson girls of the 1890s who confidently wore big hair and stylish dresses as a form of resistance against the idea that women must be silent and passive? Then you might understand where this twisted look by A Cup of Jo came from! The style isn’t quite the same as the big bouffant at the front top of the Gibson style, but the way it twist and gathers in the back mimics the idea in a subtler, modern way.

14. Backwards braid crown

Do you love the Gibson inspired look above but, if you’re being honest, you’re more a fan of braids than you are of twists? Well, lucky for us all, Xovain has figured out essentially the same style but with braids gathered at the back rather than twists! It’s always nice to have options, right?

15. Relaxed waves

We’ve outlined plenty of fancy styles here, which is great, but sometimes it’s nice to just go with a pretty, classic idea that’s simple but still stylish. Alexandrea Garza shows you how to create a relaxed, gorgeous waves that will cascade out of the bottom of your hat and frame your face perfectly.

Do you know someone living in a chilly place who’s been trying to figure out the best way to navigate styling their hair and wearing a hat? Share this post with them for a little bit of styling inspiration!