Middle age never looked so fashionable: Rouged cheeks, high-heel leather boots, fabulous hats — and these are just the costumes for the male characters of “An Evening of Cabaret,” a two-night event taking place at the Yale Cabaret Friday and Saturday to commemorate the institution’s 40th year.

An assortment of musical and burlesque acts performed by Drama students, “Evening” honors the tradition of cabaret theater by returning to decadent, musically-driven content, said co-Artistic Director Becca Wolff DRA ’09. Hence, the scandalous costumes.

According to Wolff, there was a big push this year to emphasize the “cabaret” aspect of the Yale Cabaret — a tradition that 217 Park St. has largely ignored in recent years.

“Rebellion and irreverence are at the heart of the Cabaret,” she said, citing the history and origins of cabaret theater in general. “[Cabaret] began as part of the 1930s German counterculture. It always had this controversial tinge and an element of what people were scared to see.”

But “Evening” is not the only candle on the Cabaret’s big birthday cake. Starting Wednesday of next week, the Cabaret will run a four-night “Festival of New Work,” which is — surprisingly enough — a festival of new work. Each of the three shows in the festival were either written or developed by Drama students.

“The Yale Cabaret has always been an incubator for new and original work,” said Jacob Padron DRA ’08, managing director of Yale Cabaret, sitting in his office moments before a top-hat-clad actor, in search of Scotch tape, politely interrupted the interview.

In addition to an original musical and a small-cast play, next week’s “Festival” will showcase a unique outdoor project, “In the Meantime,” directed by Patricia McGregor DRA ’09.

Wolff called “Meantime” — a device piece constructed from two existing scripts with additional improvised and extra-textual content — the “most ambitious” show of the new season. With “in the round” seating facing a sandbox square in the middle of the Cabaret’s outdoor patio, “Meantime” is thematically centered around the Iraq conflict and its media coverage.

McGregor, who is developing “Meantime” with undergraduate and Drama School students, said her show is heavily rooted in the concepts of dialogue and distraction. The improvised elements — as well as the unpredictable nature of performing outside — add “immediacy” and humor while subtracting “preciousness.”

The show stages, quite literally, Americans’ complex reactions to the war, McGregor explained. The performers will be creating their own material to be juxtaposed with one script by Tony Kushner and another by Theater Studies professor Deb Margolin. And if the audience isn’t engaged by the timely content and forum-like atmosphere, then the show’s funny moments should do the trick.

The Cabaret’s official season kicks off Oct. 6, with performances of “Mr. and Mrs. Hollywood,” a character-centered play that, according to Wolff, deals with the question of whether one can have a love affair and still remain true to one’s art.

Quite a question for the Cabaret as it enters the age of graying hair and growing self-restraint.

Not really, said Wolff. “The Cabaret has always been about change and revolution … It’s going to be a very exciting season.”