This AU/Crossover couples photo contains
fedora, felt hat, homburg, stetson, and trilby.
There might also be
boater, leghorn, panama, panama hat, sailor, skimmer, straw hat, porkpie, porkpie hat, and campaign hat.
The plot is that Cook did something (maybe the whole sophia thing. i dunno, you choose whatever) & it hurt Emily and drove her away. So you can imagine that they were either best friends before or a couple and that now he's missing her.