Who: Karlie Kloss.
When: Saturday, April 30.
Where: The annual White House Correspondents Dinner in Washington, D.C.
What: An ivory silk Derek Lam Fall 2016 gown.
Why: Last week, we revisited a few of our favorite vintage White House Correspondents Dinner photos; here, model Kloss channels the old-school glamour that defines the event. Her red lips and gentle swoop of hair are worthy of first ladies of yore, while the gown's two-toned ivory panels add a contemporary edge.