My 10 Favorite Handmade Winter Hats for Baby Boys

A few weeks ago, I went through Eli’s clothes and weeded out the ones that didn’t fit and went into the garage and got the next size up from our boxes of baby clothes. I came across an adorable outfit that had a matching hat and set of booties with blue bunnies on them that I had completely forgotten about. I got so excited to see him in it and set it out for the next day. The outfit was a little large on my petite baby (7 months tomorrow and barely wearing 6 month clothes), but the hat. Oh the hat. Basically my baby was wearing a cute little bunny yarmulke.

Sigh. I still put the booties on him, but I realized then that we have no winter hats that fit our son, just one hooded sweatshirt, which though adorable, isn’t going to cut it. And since then I’ve been on the hunt for a winter hat. It doesn’t get terribly cold here, but it gets cold enough and we’re planning a trip to the snow soon. Because we need the hat made to his specific head size and because the handmade ones are just so much cuter, I went looking at my favorite place online, Etsy.

I have now thoroughly investigated hats, ooohed and aaaahed over and over, and narrowed it down to my 10 favorites.

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  • Football Hat 1 of 10
    Football Hat
    In this house we are HUGE football fans, so a football hat would be pretty perfect. You'll see that this one is kind of the odd man out in my favorites collection, but still, totally a possibility.
    Get this hat from Lovely JC's Etsy Shop for $14!
  • Frog Hat 2 of 10
    Frog Hat
    So, my initial search didn't even turn this hat up, I was looking through this person's shop and found this one and now I'm dead from the cute. I love the little curly tongue. Definitely a front-runner for me.
    Get this hat from the LulasLovables Etsy Shop for $20!
  • Bear Hat 3 of 10
    Bear Hat
    Unbeknownst to me, I'm obsessed with animal hats. Particularly ones with adorable little ears. This bear hat is sweet and cuddly and the planner in me thinks that someday if we had a girl, this one would be easily worn by her without looking too masculine.
    Get this hat from the LulasLovables Etsy Shop for $20!
  • Monster Hat 4 of 10
    Monster Hat
    What could be more perfect for my little monster than a monster hat? Three eyes! Horns! I declare this one near perfection.
    Get this hat from azek2000's Etsy Shop for $26!
  • Bunny Hat 5 of 10
    Bunny Hat
    This one caught my eye for the fact that it's fleece, but also still pretty darn cute. I like that it'll keep Eli's head a little warmer than the crocheted hats, but isn't boring by any means. Practical and adorable.
    Get this hat from StrayHat's Etsy Shop for $25!
  • Owl Hat 6 of 10
    Owl Hat
    A friend of mine had this hat for her son several years ago and I remember how cute it was on that little baby head. I love the little beak with those big curious eyes!
    Get this hat from azek2000's Etsy Shop for $26!
  • Dinosaur Hat 7 of 10
    Dinosaur Hat
    I like this one because depending on how quickly Eli's giant noggin continues to grow, this one seems boyish instead of babyish, so it might get more wear than some of the other options. Unless Eli becomes as obsessed with animals as his mother apparently is...
    Get this hat from handsomeboyboutique's Etsy Shop for $18!
  • Elephant Hat 8 of 10
    Elephant Hat
    My husband and I are at an impasse with this one. I think it is about 700 kinds of awesome and he thinks it's not because he grew up with big ears and kids called him Dumbo all the time. I don't think I'm going to win this one, but I would be remiss if I did not include this in my top 10.
    Get this hat from handsomeboyboutique's Etsy Shop for $18!
  • Despicable Me Hat 9 of 10
    Despicable Me Hat
    You guys. Come on. This is just so cute. We love animated movies in this house and so needless to say, this is absolutely a front runner, even though it's not an animal.
    Get this hat from LovelyJC's Etsy Shop for $16!
  • Sock Monkey Hat 10 of 10
    Sock Monkey Hat
    There are several adorable iterations of this hat on Etsy, but this one is my favorite, I just love the color scheme in addition to the adorableness of the monkey. As someone who used to have a sock monkey and whose child will be getting one soon, this one just fits so well.
    Get this hat from handsomeboyboutique's Etsy Shop for $18!

Which hat is your favorite?

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