From left, Justin Roux (Jonathon/Miranda), David Jon Timm (Michael/Gloria), Ed Dionne (Theodore/Terry), Allison McCann (Rita), Michael Donovan (Albert/Bessie) and Justin Stebbins (Isadore/Charlotte) in a scene from “Casa Valentina” Linwood R. Leland photo

The red-carpet question “Who are you wearing?” becomes “Who are you when you’re wearing that?” in the latest production from the Portland Players.

Questions of identity swirl around “Casa Valentina,” Harvey Fierstein’s play about a group of men who gather at a resort in the Catskills in 1962. There, they believe they can safely get their frocks on and have a very-important-to-them good time dressing as women. It’s a thoughtful, provocative and entertaining show that raises some compelling questions.

The play treats the social risks of cross-dressing seriously while also raising broader questions of social acceptance. Laughs, mostly in the form of witticisms offered and playful zingers exchanged, help to humanize the characters who will eventually face some sobering challenges.

Married couple George and Rita run the establishment which, we soon learn, has dark clouds gathering overhead in the form of financial problems and a postal investigation regarding some explicit photos that were apparently sent to George. While everyone tries to stay in party mode, including George when he becomes his alter-ego Valentina, difficult decisions loom.

Local favorite Zack Handlen ably conveys the dilemma of his George/Valentina’s attempts to stay grounded in an urgent situation even as he teeters giddily on heels. Allison McCann’s Rita also must balance business concerns with growing doubt about her marriage. Her reactions are touching.

Michael Donovan is a hoot as the Oscar Wilde-quoting Albert/Bessie. Justin Roux is sympathetic as the newbie Jonathon/Miranda whose uncertainty about the double life he’d like to embrace draws stories from the others about their own experiences in a world that often misunderstands them.

Jeff Campbell is a reserved Judge/Amy whose secrets are under fire from Justin Stebbins’ worldly Isadore/Charlotte. The latter wants the group to become part of a national nonprofit organization, if only the members will agree to certain unnerving requirements.

Ed Dionne (Theodore/Terry) and David Jon Timm (Michael/Gloria) each have a moment to reveal some of their character’s biographical details, adding both poignancy and degrees of fortitude in their softened voices. Suze Quackenbush rounds out the cast as the Judge’s daughter who, like Rita, provides perspective on the lives of those whose love is tested.

Taking advantage of a multilevel set, director Charlie Marenghi keeps the stage action moving in what is a show given to some lengthy speeches. The period costume, makeup and hair designs are a treat to behold.

In all, the men/women of “Casa Valentina” are a lively bunch whose life stories may even give a makeover to some theatergoer’s attitudes.

Steve Feeney is a freelance writer who lives in Portland.