
1
CUTEST CHARACTER HAT
Pennington Bear Company Original Sock Monkey Hat

Your little monkey will look so, so sweet in this quality earflap cap: Just toss it in the wash when it needs a good cleaning! The tassels are so sweet, and the whole thing is designed with cute retro styling in mind for your little one.
It’s an adult size, but it runs pretty small, which makes it great for kids who are a little older, or for babies with bigger heads.
More: These Christmas PJs for Your Baby Are Cute and Comfy
2
SUPER WARM
Zando Baby Boy Sherpa Lined Warm Fleece

Sure, your little lumberjack may be too wee to get out there and split logs, but they’re not too small to rock a warm, fleece lumberjack hat and mittens.
The combo pair is both fleece and fleece lined, which makes it super warm, and also extremely durable and washable. While it’s both machine-washable and dryable, it’s best to let it air dry to keep the fluff factor high.
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3
BEST TRANSITIONAL
Baby Hats Girl Winter Hat with Pom

Puff hats are a classic for a reason. They’re the timeless choice for basically anyone, but you’d be hard-pressed to find someone who doesn’t love the look of a baby in a puff hat. This hat is made of a thinner cotton knit for transitional dressing, and the puffs are delightfully oversized.
4
MAGICAL GOODNESS
Knitted Pixie Hat — Super Soft Baby Yarn Bonnet

Babies are already pretty darned magical, so why not emphasize that point by putting them in a little winter pixie bonnet? Honestly, you probably never knew you wanted a fairy bonnet for your baby that’s knitted with cotton and acrylic in three fantastic shades, but now that you do, can you ever go back? Do you even want to?
This hat is incredibly soft and breathable, and the stitching in the weave is smooth and comfortable over little ears and faces. The interior has no rough seams, which is a good thing, since many babies hate them. (Mine certainly did.) The tie straps are equally as soft, so keeping the hat on the baby shouldn’t pose a challenge.
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5
WASHABLE AND EASY SET
Simple Joys by Carter’s Baby Hat and Mitten Set

At some point in your baby’s life, it’s imperative that they have a hat with little bear ears sewn in. We didn’t make the rules, but we do advocate for them. Because seriously? Look at this fleece hat and mittens set by Carter’s. They’re machine-washable sherpa material, and feel like heaven against the skin.
6
A CLASSIC FOR A REASON
Carhartt Watch Hat

$13 AT AMAZON$13 AT DICK’S SPORTING GOODS$15 AT BED BATH AND BEYOND
Designed like the classic Carhartt adult beanies, this tiny baby version will keep your little one’s head warm during the frigid months. Grab one for yourself for a twinning moment. (And don’t forget to take all the pictures.)
The beanie is made with a tight knit weave in a combination of textiles, which means that it’s not only durable, it’s also warm, weather-resistant, and washable.
7
BEST FOR CURLS
Satin Lined Marley Autumn Toddler Beanie

Got a kid with curls? We hear you. This satin-lined cap will keep your baby’s coils frizz-free and full of volume, while keeping their head warm and comfortable. The satin material is breathable enough to let air circulate, but warm enough to keep heat in. It’s basically a warm bonnet, and it works beautifully.
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8
BEST KNIT OPTION
Bestknit Baby Hat

This cute knit baby hat features a stylish strap fastened with precious wooden buttons, and it’ll look absolutely perfect with the right sweater and khaki pants! It’s giving us “royal baby living in the United States” vibes, and we love to see it.
9
BEST FITTING FOR BABIES
Exemaba Beanie Earflaps Hat

Double the pom poms, double the fun! This cotton-acrylic blend hat fits snugly onto your baby’s head for extra comfort. The cozy ear flaps keep the biting frost away.
The straps are two single-knit woven straps that keep the flaps from moving, which helps keep the hat on. Babies love to rip off a hat, so there’s no need to make it easy, right?
10
GREAT TWO PACK
Alepo Fleece-Lined Baby Beanie Hat (2 Pieces)

The chunky knit outside of this Alepo Baby Beanie complements the fleece-lined interior perfectly. Fluffy and soft, your tot isn’t going to want to take this cap off, because they’ll be to enamored with the cozy softness of it all.
Plus, if your child gets one dirty or has different-colored coat options, the two-pack is a wonderful, affordable option for parents looking for an economical choice.