When I was growing up, I genuinely hated hats. They fit terribly, would hurt my head and would feel like they were squeezing my skull. So when other girls would pop a cute hat on for "no wash days" or because they woke up late, or to keep the sun out of their eyes while on a walk or at a farmer's market, I genuinely thought it was a form of fashion pain. That they were all lying about choosing to wear hats, like when people tell you that wearing high heels is as comfortable as sneakers.

And then one day, while in the Subtle Asian Traits Facebook Group, I learned that snowboarding helmets came in three sizes. Youth, Adult & Asian.

Because our heads are shaped differently. So I did a deep dive. I bought 13 hats to find one that was comfortable, that looked good, that didn't squeeze my head, and I found it.

Watch this video for a Fit Check.

Bright, breezy, and full of Midwest sunshine, the Head in the Clouds • Chicago Hat captures the spirit of the Windy City on a perfect summer day.

Inspired by the endless blue skies and the shimmer of Lake Michigan, this hat features “CHICAGO” embroidered in soft butter yellow bubble lettering across a sky-blue cotton cap. It’s a cheery, everyday essential for those who love the city, and the friendly people in it.

Whether you’re wandering around the Garfield Park Conservatory, ice skating in Millenium Park, or daydreaming under a cloud-spotted sky, this hat is your wearable reminder of where your head, and your heart, belongs.

Also available: San Francisco & Seattle Hats

PRODUCT DETAILS •

• "CHICAGO" text is in butter yellow with a very cool 3D effect that can be seen from very far away. The letters were hand drawn by Samantha to resemble Mylar balloons and clouds.
• Embroidered in Seattle, WA
• The cap is unstructured and will lie closely to the head
  
• It includes 6 Panels which makes it better fitted
  
• It has a slightly pre-curved visor
• It features a Tuck Strap with Slide Closure for a custom fit

SIZE •

• The short answer is this hat is One-Size-Fits Most and includes an adjustable strap that is tucked into the interior of the hat for a fitted feel
• Min Circumference: ~ 50cm/19.5"
  Max Circumference: ~ 64cm/25"
• The long answer is that a few years ago I learned that Asian heads are shaped differently. So my entire life I have been under the impression that I had a large head - in reality, it is simply differently shaped which is why free novelty hats, and hats I would try on at the hat store in the mall (you know which one) never fit me.
  
  I learned about this in my SAT (Subtle Asian Traits) Facebook Group where they talked about snowboarding helmets. (I know, but I warned you that this was the long answer before you even started reading this!) So when I started researching hats I bought 13 different hats to see which one fit the best. Because the fact of the matter is that I wanted to sell a hat, it was going to fit my head. And if it fit my head, it would also fit almost everyone else's heads too.

MATERIAL •

• 100% garment dyed and washed cotton twill

CARE •

• You can either hand wash, spot treat or machine wash your hat! Maytag wrote a very complete article on how to take care of your hat, including vintage hats, that you can find here.

All sales are final on apparel.