Instinctual gender identity?

Conversation last evening...

"Ugh- I despise picking out my clothes for work. Hey Jaysen- what do you think I should wear to work tomorrow?"

"How about a pretty skirt?"

(Ugh- a skirt) I retreat to the recesses of my closet and produce 3 options for him.
"Okay, which one of these?"

Jaysen inspects all 3 specimens carefully. "Uh...the flowers!"

"That's a great choice, thank you for helping me out!"

"Yeah. You wear a skirt, and your 'work-man' (bossman) will be so happy and proud."

Erp?
Is my son inferring that my boss would appreciate it of I dressed more girly?
Things that make you go hmm.