Ollie passed on a birthday sweater this year and instead wanted a stocking cap. He had specific details that I tried to capture. I spent way more time time doing research, swatching and designing than knitting. The goal is a snug fit, close to that of a baseball cap.

The yardage used as noted above is for the entire hat, including the white yarn.

Purl Soho is an excellent resource for designing a hat. The shaping is what she calls a box hat with the decreases only on the sides and a grafted closure at the upper end.
Purl Soho Box Hat
How to Knit the Right Hat Size
She advises negative ease in a hat. I may have gone too far with that, guessing that he is at the low end of the Child 18-20” range.

CO 76 sts. Motif is an odd number of sts so when planning the dec, one side has an extra dec to get to an even number for grating while maintaining the motif in the center front.
Finished dimensions:
16” diameter in center of bubble, unstretched
Ribbing 3.25” from CO
Height: 9” from CO to top of crown; St St section: 5.75” total: from ribbing to top of crown, 3” to start of dec, dec to crown 2.75”.
This yarn is very soft which is why I chose it. Since Ollie lives in Oregon where the temps seldom dip below freezing, I think this blend will be warm enough. It washes up beautifully. The gauge noted above is post-blocking by machine wash & dry. It varied only slightly from the pre-blocking measurements.