25 Winter Hats You’ll Love

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Stylish winter hats

Hats, clockwise from the top left: 1, 2, 3, 4, 5

It seems as though winter has arrived overnight. These days, you might have to defrost your car before you can drive it. You’re probably craving things like hot chocolate and chicken noodle soup. And it’s not just exhaustion keeping you from getting up for your 8 am class – the mere thought of trekking across campus in the freezing wind is enough to make you consider forfeiting attendance points. (Not that you should, of course!)

Now, I know you lovely CF ladies are too responsible to let a little bit of inconvenient weather get in the way of your education (right??), but just in case, I know of an  essential accessory that really helps make the cold more manageable. Girls, meet your new seasonal best friend — the winter hat.

In this post, I’ll list a few reasons why I can’t survive without my trusty hats during the winter months. After that, I’ll share 25 super stylish winter hats if you’re in the mood to shop. Read on, girlfran’s!

Why We Love Winter Hats

  • Duh — they keep you warm! You’ve probably heard this before, but most of your body’s heat escapes from the top of your head. Fight this by covering your head and ears with a fashionable hat.
  • They look intentional. While your coat’s hood may keep you warm, it won’t look nearly as chic as a hat. A hood looks like an afterthought, while a hat gives off a put-together vibe. Give one a try — you’ll be surprised at how much more stylish you’ll look and feel.
  • They hide undone hair. One year of college, I lived in this little cottage built probably 70 years ago. While it was adorable and a fun change of pace, the house wasn’t well insulated, and therefore super cold all the time. Keep this a secret, but I was really lazy about washing my hair that season (who wants to step out into a 50 degree bathroom?)… and thanks to my hat collection, I was able to hide it. The great thing about chic winter hats is that they’ll cover up your greasy roots while still showing off your shiny tresses.
  • You’ll look fashion-forward! It’s surprisingly daring and bold to rock a hat on college campuses, especially if you opt for a bowler style, wide-brimmed fedora, or furry trapper hat. Wear your secret weapon with pride knowing that you look cooler AND feel more comfortable than those around you.

Hats You’ll Love

Trapper Hats

I love the rustic, wintery feel that a trapper hat gives an outfit. These hats will look great with most outfits, but I think they work especially well with “snappy casual” type ensembles appropriate for classes, group meetings, and tests. Wear a trapper hat with your favorite skinny jeans, boots, a knit sweater, and a peacoat for a classic cool look.

Winter trapper hats

Hats, clockwise from the top left: 1, 2, 3, 4, 5, and 6


Whether you prefer a slouchy or fitted style, a beanie can do wonders for making a last-minute comfy outfit look stylish and intentional. Wear a beanie with a pair of leggings, combat boots, your favorite graphic tee, a boyfriend cardigan, and a parka for a cozy-yet-chic ensemble.

beanie hats

Hats, clockwise from the top left: 1, 2, 3, 4, 5, and 6

Structured Hats

Am I the only one who’s completely crazy for the bowler, wide-brimmed fedora, and boat hats we’ve seen on all the style blogs lately? I love all of the styles because they are bold, super fashionable, and look great for nights on the town when you want to look chic but still stay reasonably warm.

Try one of these types of hats with a long-sleeved minidress, leggings, and ankle boots. This way, you’ll have a little extra protection to keep you warm if you plan on going to a bar that doesn’t have a coat check area.

structured hats

Hats, clockwise from the top left: 1, 2, 3, 4, 5, 6, 7, and 8

What do you think?

Do you have a “go-to” winter hat? What kind is it? What are some of your favorite ways to style a hat? What other tricks do you use to stay warm but still look chic? Are there any other topics that you’d like to see here next? Leave a comment and continue the discussion!

5 thoughts on “25 Winter Hats You’ll Love”

  1. Weird! Had just finished pointing out to friends that people don’t wear hats often enough when I saw this on CF! I love woollen beanies and the classic pompom ones, I have a lovely collection that’s reaching 25 winter hats I love status!

  2. Love the knit hats – they don’t give you hat head or ruin your hair. I think structured and snug knit hats are more chic especially when you have your hair down around your face.

  3. I absolutely love hats and have since middle school. I have a huge head, though, so I’m used to hats sitting on top of my head instead of really on it. Now I have a super-cute bowler that’s actually the right size, but it flattens my curls into really awful hat hair! I love it anyway, but it’s pretty awkward taking off my bowler to reveal completely flat hair above a big ring of frizz.


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