What to wear to pajama day to impress a guy?

see i have a big crush on a guy, and i want to plan ahead for "spirit month." theres pj day, school colors day, dress for success, hat day, and fave team day. i have everything planned out, but idk whether to go with cute plaid aerie shorts and a tee, or to go comfy. remember, tryin to impress a guy!! :D