How to Wear a Beanie

“It’s pretty self explanatory,” says Kendra. Just pull on the beanie, tilt it back on your head, pull the top part back and down, and tuck in your hair. “I was always trying to wear a more tailored hat but it looked kind of uptight. The slouchie look has a much more relaxed vibe, and I think it gives you more street cred!”

How pretty does Kendra look?
Thanks, Kendra!

P.S. Kendra’s navy nails.

(Photos by Alpha Smoot for A Cup of Jo. Styling by Kendra Smoot. If you’re wondering, Kendra’s beanie is from Madewell (now sold out), her snood is from French Connection, her jacket is from Madewell, her bag is vintage Coach and her boots are Sam Edelman)

  1. what is with all these lazy kids and their slouchy, slacker beanies?? back in my day we wore knit caps so tight, you couldn’t think if you had one on. those were the days. goddamn kids these days wearing everything too large. it started with jinkos, now who knows where it will end!!!!

  2. So informative post , How to wear a beanie, very popular due to the comments are witter , thanks
    Winter Hats For Women

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  4. I have a big head too and had pretty much given up on wearing any sort of hat – until now!
    Time to shop for a cute Fall/Winter beanie!

  5. Absolutely love how you are styling your beanie looks effortless!

  6. There’s a reason why I go to different blogs, and that reason is to find these amazing tips when it comes to hairstyles and just fashion in general. Having these information is very valuable to me, even beauty salon adelaide has been trying to get more information over the internet for any new fashions or hairstyles.

  7. I like beanies of the beret type, especially on my teenage daughters, and especially when the berets in question happen to be among those handed down to us by my legendarily lovely mother, who died of lung cancer fourteen years ago. Just the other day, my girls each had on one of her hats–my older daughter, the beige beret; my younger daughter, the black one. I wondered whether my mom had occasion to notice, wherever she might be, that the two girls born on her birthday were now jauntily wearing the hats that once covered their grandmother’s bare head. Three cheers for the right hat!

  8. some guys i know started a beanie company called krochet kids. they teach women in developing nations to crochet, and then sell their beanies in the States. really cool model to empower women in developing nations. every hat is signed by the woman who made it, and you can read about the different women on the website. check it out here:

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  10. big heads can wear hats! my head is huge – my husbands hats are too small for me to wear – but i wear hats often and always get lots of compliments. you just need to pick the right ones!

  11. Lovely!

    I have a big head too. I just purchased a beanie with a pom-pom on it. Can’t wait to experiment tonight.

  12. Darn, I just fell in love with those Sam Edelman boots… quick, someone talk me out of buying them!!!

  13. Beanies! Can I shamelessly advertise for a friend recently out of art school with a degree in fibers? She makes some pretty fantastic scarves that are hand-woven, and dyed too!

    Help an artist and part time barista who still lives with her parents to survive out! Thanks for indulging me.

  14. Slouchy hats all the way!

  15. Great tips. Trench coat in carmel color is lovely. I think it is important to keep in mind that beanie in a contrast color will bring a new look to the outfit.

    stop by

  16. Such a great post! Would love to know where Kendra’s rings are from. So pretty!

  17. This is EXACTLY what I do! I look terrible with my forehead covered and my hair pulled back. This definitely works for people who don’t look good in regular toques! (it seems so strange to a Canadian that you guys call them “beanies”. A beanie to me has a propellor on top of it). Thanks Joanna!

  18. This is how I wear my beanies :) I love them! Especially because I crochet them myself and can make them the right shape for my head!

  19. Thanks for sharing! Love her style.

  20. Oh, love this! I have a beanie and for the life of me couldn’t make it look cute. Can;t wait to try it out again.

  21. I must try this!!!!! Thanks

  22. she looks great, i love the slouchy beanie look! so relaxed yet chic!

  23. Are all your friends beautiful? It sure seems so!

  24. Yep, I have a hat like this and it’s pretty self explanatory how to wear it. It’s the only hat that looks good on me!

  25. Beautiful! Question: does anyone know where this picture was taken? the wood door and stone wall in the last image are gorgeous!!

  26. My head is too small

  27. My head is too small

  28. beanies always pop off my (big) head. boo.

  29. D says...

    It does look nice. But Good Lord, it does NOT give you “street cred”.

  30. IT WORKS!!!!
    I also think I look horrible in hats but I went to the mirror and had a go! VOILA!
    Thank you

  31. Where are her jeans from? Thanks Joanna!

  32. This is exactly how I attempt to pull off a slouchy hat. The only problem is then trying to get it to stay on, especially if my hair is freshly washed or it’s windy out.

    Sometimes, if it’s a fairly open weave, I’ll sneak a bobby pin in and actually secure the hat to my hair where I’ve tucked it in beside my face.

  33. LOVE this! So darling.


  34. what to do when I pull it off and my super fine hair goes sticking out in every direction!? what a beautiful photo subject though!

  35. I have the opposite problem – a baby peanut head. Which is just too bad because as much as I love hats, they always make me look bald. But this just might work!

  36. I can’t wear hats either. I still don’t think I could pull this off. :( Next up… how to prevent hat hair?? ;)

  37. I thought a snood was that net thing-y you wear over your hair in the back ( a la Barbra Streisand in The Way We Were)?
    Also, as a Canadian, I much prefer saying toque rather than ‘beanie’!

  38. I love beanies! So cozy!

    Love the pictures as well.

  39. Oh, I bet my head is bigger. For fun sometimes, my husband and I try hats on me. The wee little dainty ones make me look like Stan Laurel.

  40. This pictures are gorgeous! I love beanies: they keep my head and ears warm, they add a nice touch to the puffy winter outfits and they are an excellent way of saving a bad hair day!!! Win win win!

  41. Too cute – a slouchie beanie is my go to, bonus: it also helps with fly-aways when it’s foggy or rainy out. A must in San Francisco!

  42. Yes, Kendra certainly pulls off the beanie look with glam and street cred :) You’ve convinced me to to give it another go…..
    Lovely pics by the way XX

  43. Beautiful beanie and trench !
    She is lovely!

  44. Looks super cute. I always feel like I look funny in hats as well! But you’v inspired me to give it another go!

  45. hm. i am doubtful that i can pull this off, but i will give it a shot. it certainly looks cozy and warm.

    i too, have quite a large head, joanna. i have to buy all of my structured winter hats in the men’s department.

  46. AH! I feel the same way about hats. I SO want them to work on me and I just feel like they look goofy. I’ll try this tip and see what happens. Thanks!

  47. my biggest problem is feeling like it looks too contrived. i don’t like it when girls where beanies and pull their bangs out where it looks super styled. kendra has managed to pull some hair out without it looking too done. bravo!

    • I don’t get it. I wear slouchy winter hats all the time in the cold weather… but my bangs still sick out without effort. How are you putting your hat on? I just pull mine over the top. My hair stays where it was before.

  48. Wowza one of the most gorgeous women to grace the pages of your blog! : )

  49. “Beanie” is so weird to me – in Canada we call them toques (pronounced “tooke.”)

  50. Sadly this only works with long hair! Wish my hair could look like hers!

  51. That’s how I wear my hats, and I’ll never go back! It has a seriously chic and urban vibe with out seeming like you’re trying too hard. Everyone looks good like that!

  52. We in Canada call this a toque—much more chic sounding than a “beanie”, which sounds like a hat with a propeller on it!

    You crazy kids down south… ;)

    • Johanna– My name is also Johanna and I just commented EXACTLY the same thing below and then searched “toque” to see if any other Canadians had commented. Ha!

  53. I could never pull that look off. A slouchy beanie doesn’t work with my pixie cut. (sad panda)

    • Agreed! I never wear hats because they look weird with my pixie cut (I also have an unusually small head…). What is a pixie to do!?

  54. ha! this came at the perfect time. i bought a beanie at H&M the other day because 1) it was cheap (duh, it’s H&M) and 2) i’ve been determined to wear one this winter. buuut it didn’t quite look right. she, of course, looks adorable.

  55. That scarf is so great too! I never wear hats because I think I look like a pinhead, but maybe I’ll try this out!
    Kate at

  56. Just bought a new hand-knit slouchy beanie on ebay and I can’t wait to get it. I love hats! All hats, erm, except ball caps .. they look lousy on me. That is a very nice one that your friend Kendra has.


  57. Beanie’s are a great accessory for the autumn and winter. Love them!

  58. She’s beautiful! :)

  59. I love her beanie!! I don’t wear my hair down enough to pull off a beanie..maybe this season I will!! =)

    Ergo – Blog

  60. She is gorg! Love these tips!

  61. I love wearing slouchy hats in the fall and winter! For me, it’s the one type of hat I can pull off!


  62. Great tips and she is so adorable. Btw: her trench coat rocks. Kisses