1. Grumps Face Pom Beanie ($29): You might not be thrilled about the onset of winter, but this topper’s laughable grumpy face and fluffy pom pom make it all a little more bearable.

2. Topshop Faux Fur Pom Beanie Hat ($26): Funky and fiery, this knit faux fur cap is ideal for warding off “meh” vibes associated with gloomy, gray days.

3. Chiara Ferragni Flirting Beanie Hat ($209): Okay, so it’s a bit of a splurge, but with this fun, flirty hat, even negative temps won’t be able to get you down.

4. J.Crew Ribbed Cashmere Hat ($78): With its soft cashmere and a vibrant hue, this winter staple has you covered indoors and out.

5. Penfield Sanford Pom Beanie ($35): Not only is this retro-inspired number easy on the eyes, but it has the whole warmth thing on lock too. Pair it with your favorite puffer, or better yet, a long boyfriend coat.

6. Urban Outfitters Shimmer Ribbed Beanie Turban ($24): A fresh take on the classic beanie, this chunky knit turban gives off major boho chic vibes.

7. Kate Spade New York Fox Beanie ($68): This crazy cute topper is totally game changing. Besides brightening up a cozy getup, it might even make you excited when temps take a drop.

8. Free People Cuff Beanie ($48): Soft and slouchy, this heavy-duty knit cap pairs perfectly with a fresh athleisure ensemble and snuggly shearling pieces.

9. Reason Woodsman Plaid Pompom Hat ($28): Flannel tops aren’t the only way to get your plaid fix this season. Inject your getup with a little woodland flair with a bright bold buffalo check toque. It’ll have you dreaming of all the fab things fall and winter bring, like roaring fires, fresh pine scents and maybe even a glass of mulled wine (or two!).

10. Eugenia Kim Mika Hand-Knit Cable Beanie ($225): Like your favorite chunky sweater, only for your head, this brilliant knit hat is vying for a place in your cold-weather rotation.

11. Forever21 Zigzag-Patterned Beanie ($10): Going bright isn’t the only way to set yourself apart. A black and white graphic cap will turn heads and go with everything in your closet. Now that’s a win-win.

12. Rag & Bone Petra Beanie ($125): Made from super soft and incredibly warm mohair, this striped number will help ward off cold and bad hair days — no hat hair here.

13. Almer Hats Powder River Pom Beanie ($48): You’ll be pretty in pink when you top off your ensemble with this furry knit number. Create cool contrast by pairing it up with a leather jacket or a structured car coat.

14. Topshop Cat Ear Beanie ($26): Think outside the box when it comes to choosing your winter accessories. Channel your inner cat lady (because why not?) and top off your look with a super cute cat ear cap.

15. Frederica Morretti Knit Wool Beanie With Bow ($70): Balance out this hat’s flirty, feminine feel with leisurewear staples, like joggers, sweatshirts and vibrant trainers.

16. Topshop Chain Hand-Knitted Beanie ($30): One look at this bright beanie and you’ll be smitten. The candy-colored hue, texture and statement pom add a playful touch to your look while keeping you incredibly warm.

17. Aqua Embellished Beanie ($88): Who knew beanies could be so glamorous? Decked out in shimmery stones, this navy chapeau will shine bright all season long.

18. Eugenia Kim Margeuritte Knit Beanie ($161): It’s time to put on your thinking cap! Eugenia Kim reimagines her iconic “Do Not Disturb” floppy hat for a winter-appropriate alpaca beanie featuring playful typography.

19. Free People Hans Climber Beanie ($38): Laid-back and cool, this oversized beanie is the perfect complement to any off-duty outfit.

20. Local Heroes Bad Hair Day Beanie ($26): This sassy topper was made for days when your mane just isn’t on top of its game.

21. Rosie Sugden Cashmere Leopard-Print Beanie ($170): Leopard is a print that will never go out of style, so you’ll look on-trend for years to come in this soft cashmere topper.

Will you be rocking a beanie this season? Tell us in the comments!