Designed by Plaza Hotel architect Henry Janeway Hardenbergh in a German Renaissance style, the room had walls of English or Flemish oak, frescoes of Bavarian castles (by a painter whose identity is now lost to history),[5]: 52  faux wine casks carved into the woodwork, and, hanging from the 20-foot ceiling, a grape-laden chandelier topped by a barmaid hoisting a stein.

[3] In 1971, critic Ada Louise Huxtable contrasted the "dignity, scale and period authenticity" of the Oak Room to other more modernized spaces in the hotel.

[5]: 15 [7]: 142 [11]: 55–56  In February 1969, Betty Friedan and other members of the National Organization for Women held a sit-in to protest this; the gender restriction was removed a few months later.

[13] The hotel alleged that the restaurant owners had failed to pay the rent, among other matters, but a major point of contention was the "Day and Night" parties held on Saturday afternoons.

Lady Gaga appeared in impromptu performances with Newman in the Oak Room on September 29, 2010[17] (wearing a dress made of hair)[18] and again on January 5, 2011.