Great Winter Hats for Boys

For Younger Boys

Animal-themed hats are all the rage this winter for boys and girls alike. GapKids offers adorable designs and plush construction in toddler sizes, which fit little boys ages 1-5. Choices include a fleece shark hat for $16.95, an adorable fleece-lined, faux-fur yeti hat and faux-fur wolf hat (each for $22.95), and a knit "friendly monster" hat for $22.95. Each of these hats feature long ear flaps to ensure a snug fit and chill-proof wear.

The Children's Place is an affordable option with hats all priced under $10. Toddler boys ages 1-4 can masquerade as a shark, zebra, dog, raccoon, frog, or bear. These fleece hats range in price from $7.95-$8.95. Non-animal hats are available also, like the popular 3-in-1 fleece hat that features fleece, a chin strap, and a cute pom-pom for just $6.95. Colors coordinate with other items, like Children's Place's 3-in-1 jackets and scarves. Cozy marled knit hats convey a sporty look that's grown up, with no chin strap but ample room to keep ears warm. The marled hat sells for $7.95 and is available in either navy or olive with contrasting stripes.

Old Navy hats are a seasonal favorite among parents. Toddler sizes for ages 1-5 often come in a set with mittens, all for less than $20. The Performance Fleece Hat and Mitten Set in particular is a bestseller year after year; it features blue stripes, color block blue, color block red, green camouflage, and frequently goes on sale. Fair Isle Hat and Mitten Sets are also available for $19.95 and feature a dressy look. And finally, not to be outdone by their competitors, animal themes also abound here, including an owl, donkey, monkey, and more, and licensed character hats like Elmo and Cookie Monster are also available. These hats sell for $19.95.

For Older Boys


Older boys may be more active in winter sports and require hats of better quality and performance. L.L. Bean is a favorite among parents for durable accessories, excellent return policies and positive customer service. Frequent coupons also make this store a favorite. For biting winds or serious winter athletes, the Trail Model Fleece Balaclava is a breathable hat and cover-up that protects the face, featuring an opening for just the eyes. At an affordable $14.95, this is one instance in which you get more than you pay for as reviewers left glowing reviews for this product.

For hand-knit wool that also lends a hand to fair trade, Everest Designs hats are a must-buy. Sold at sporting good stores like REI and others, these hats are crafted by a women’s knitting cooperative in Nepal and offer supreme warmth with unique Fair Isle designs. Polar fleece lining ensures extra warmth, while the wool wicks away moisture and keeps its wearer warm even when wet.