Tis the Season for Very Cute Hats

Tis the Season for Very Cute Hats
With the weather changing even down here in the South (hooray!), I can finally rationalize shopping for fall-ish clothes for my kids, like sweaters, coats, and, of course, hats. Particularly if they include the handmade Flipside Hats found at the wonderful boutique Cat in an Apron--a reference you might recognize if you're a Free to Be You and Me fan.

My fave for fall is the blue denim which reverses to khaki and black plaid (shown). So if kids get tired of one side, they can flip them inside out for a totally new look. They're lightweight enough to stave off hat head too. Not that hat head can't be totally cute on a kid once in a while. -Kristen

Congratulations to Keck H, winner of the Flipside Hats from Cat in an Apron!

Share this story

Pin

More in KidsView all picks →

Illustration of three smartphones and a kids' smartwatch with location, signal and Wi-Fi icons
Sponsored

Phone plans for kids, compared: what a first phone line really costs in 2026

From free lines to $65 a month: what a kid's phone plan costs at AT&T, Verizon, T-Mobile and the cheaper carriers, plus kid-safe phones and watches.

Bijou Build adaptable and portable playgrounds

Bijou Build: a modular outdoor playset that grows with your family

Start with the Mainstay and add accessories over time • Panels are woven from recycled water bottles and resist moisture and UV

Collage of holiday gifts for kids, including a Ms. Rachel Toniebox, a LEGO Wallace & Gromit set, a gingerbread house inflatable bed, a drawing robot, a scooter and a red wagon

The Cool Mom Picks 2026 Holiday Gift Guide for Kids

Our annual holiday gift guide for kids: screen-free favorites, LEGO, bikes, books, cozy PJs and the hot toys kids are asking for this year.