Ahead Of The Game: A Guide To Amping Up Your Hats This Winter

Hats are a wondrous double hitter in winter. Wanna look great and stay warm? Thanks hats! But there are so many chapeaus to have; how will you decide which ones are for you? Regardless of your personal style and/or gender presentation, there are certainly several hats for you. There are levels to daring headwear, and you’re about to get in the game!


Warm, small and very portable, knits caps or beanies (toques for us up North) are a popular and accessible choice of headwear. Whether it’s a little topper from a high street store like H&M or Forever21, a homemade gem or from an Etsy shop, this is the easiest winter hat to wear. Everyone, yes everyone looks great in a beanie. Like all hats, it’s about finding the shape that suits your head/style. Some like a slouched fit, whereas others (myself included) love a little perched hat. Some prefer a tight knit, while others spring for thick, chunky yarns. You just have to find the right one! My indispensable winter toque was a lucky find at a local vintage shop, coming in at a smooth $5. Readily available and affordable, a beanie will look cute with every damn outfit! Whether it’s something super casual (like jeans and a lil’ sweater) or a full skirt with a jacket, I love the versatility of a simple and cute knit hat.

beanie layout

(clockwise from left) BDG Cuffed Rib-Knit Beanie // Multi-colored Pom Beanie Hat // Brrr Graphic Beanie // Wildfang Portland Beanie // Tomboy Beanie


So you’ve mastered a lil’ knit hat or two, and you are looking to advance your hat wearing with finesse. In comes fedoras, poor boys, berets, woolen caps and other short brimmed felt and knit hats. Hats like these were once commonplace, assumed to be a part of your daily uniform in the early 20th century. In modern times, they are often viewed as a more formal choice, but it’s not always true. As exemplified by Alex, you can throw on a short brimmed hat with a bright coat, dark jeans and oxfords, looking both relaxed and put together. Although hats never really go out of style, they’ve fallen back in favour for several winters now.

Many of the hats of the market are made of wool, which is excellent for keeping your head warm. If wool makes you itchy, there are plenty of synthetic/non-wool hats to be had. Be sure to check the fiber content if you know that you have sensitivities to certain textiles. Whether you like your hats sweetly femme or delectably handsome, there are plenty of short-brims for the taking.

mid size hats layout

(clockwise from the left) Wool Boater Hat // Pieces Wool Beret // Brixton Hooligan Cap // Colour Block Fedora // Fuzzy Band Cap


Once you’ve elevated your hat game, time to widen your horizons. An expert hat wearer is unafraid of big brims and tall peaks. Boldly stylish and a theatrical choice, a larger hat looks perfect with an equally dramatic outfit for extra oomph. A cape or statement coat look stunning with an over-the-top topper. If that’s not your style, I love the look of large brimmed hats with a something simpler. A sweater, jeans with tall boots and a cozy scarf are a great match for a richly hued bold hat! Regardless of if you dress it up or down, you’re sure to get compliments aplenty for bravely wearing a standout hat.

brixton westward fedora

fire walker hat wildfang

pippin hat need supply
(from top to bottom) Westward Hat // Fire Walker Fedora // Pippin Hat

Which hat style is your favourite? What styles have you been peeping this winter?

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Lydia O

Lydia Okello is a feminist, body positive, queer personal style blogger. On her website Style is Style, she showcases her panache for bright colors and power clashing. When she isn't pawing over Samantha Pleet collections on Tumblr, she's dreaming about havin' a kitten of her own one day. You can find her on Twitter, Tumblr and on her personal blog.

Lydia has written 64 articles for us.


  1. this was the best detour my morning could have taken! i love hats and it is definitely getting to be hat season. thank you lydia for this gem!!

  2. These hats are all so cute! I am also a big hat fan. All the “intermediate” hat choices are adorable, but how do you keep your ears from getting cold? For a winter hat my main concern is keeping my ears warm. Maybe I just have really cold ears? Definitely gives me some ideas on how to expand my hat collection, though.

    • I personally recommend those earmuff things that wrap around behind your head, they’re so discreet and warm and probably wouldn’t interfere with any hat that didn’t cover your ears! They are also good for stealth warmth, if you have long enough hair.

  3. I am eyeing a few of those expert mode hats for winter! I’m feeling a wide brim and switch-out embellishment :D

  4. My winter hat is a white camo bomber with rabbit fur lining that I got at Cabela’s. I don’t mess around when it’s cold, y’all. Even though these hats are cuts.

  5. I cannot Hat. It’s impossible. I look weird every single time. Especially in beanies. How do the kids these days get them to perch perfectly on the very back of their heads?

  6. Aahhh everyone here is so cute! I’ve always been a hat person, even as a kid. They just felt… safe. Sometimes I even wear double hats to keep warm! So I’d consider myself to be approaching hat-expert level. But I’ve never really tried truly wide-brimmed hats before! Those all look so stunning, and now I’m inspired to buy one and try to pull it off!

  7. how do yall get hats to stay on your darn head when it’s windy, though??? I feel like a major component of winter is wind….

    also seconding queer girl above: all hats look weird on me! I have one hat. it is a louise belcher hat. it still looks weird on me but people are distracted by the pink bunny ears.

  8. I’m a bit of a hat snob and I’m usually always wearing one. Panamas and Trilby hats in the summer, whip out the wool wide brims (always fixed; floppy brims are a bit too femme for my tastes) for fall and winter. I do have to disagree that everyone looks good in knit hats and beanies. I have short naturally curly hair similar to Ilana Glazer and I look like a tween boy getting ready for his Bar mitzvah in one of those hats.

  9. Hat sourcing question- where are good places to find hats for ladies with larger than average craniums? “One-size-fits-all” is always wayyyyyyy too small for me, and I find that Target and H&M rarely have sizes other than S/M or one size fits all.

    • I have a big head and a mane of thick curly hair. Hats marketed towards women are sometimes cut smaller so try the men’s section. Also, try a hat shop that has folks who can fit you properly. If they’re located near you, I highly recommend Goorin Bros and Chapel Hats. :)

  10. I am all about the heavy knit hat in the winter. My southern California sensibilities just don’t understand weather below 70, so the warmer the better!

  11. I love hats! The pippin one is especially calling my name. This is such a great article! I apparently have a thing for girls in beanies also because those pics were seriously fine…did you just google cute girls in beanies? I think I am just about to waste the rest of my afternoon doing just that….

  12. I love these hats! This year’s hat shopping has been a challenge for me since I’m only looking to wear hats with satin or silk linings to protect my natural hair from snags and drying out. It’s been hard to find beanies like that. I’m crafty though so I’m thinking of making my own.

  13. Hey Lydia nice blog..

    All the caps are amazing here. I am also a caps lover and always keep on searching for unique style caps. Specially I love to wear bucket hat. Because these hats give amazing look to any outfit.

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