Ashleigh Howard mentions to Dean Bowman that she thinks Ferris Bueller is her generation's Gatsby. Alan Ruck, who plays Dean Bowman, played Ferris Bueller sidekick Cameron Frye in the movie Ferris Bueller's Day Off (1986).
Dean Bowman (Alan Ruck) addresses his wife as "Sloane". This was the name of Ferris Bueller's girlfriend in "Ferris Bueller's Day Off", which also starred Alan Ruck (as Cameron).
At the party, Cappie is dressed in the same outfit Robert Redford as Jay Gatsby wears when reuniting with Daisy in the 1974 film version of "The Great Gatsby."