Drag

Drag is the practice of a man wearing women's clothing. There are a number of characters in the series that do this from transvestites to Larry having to dress in women's clothing for disguises.

If Larry attempts to put on gown in LSL6 he comments:
 * You don't really want to wear the gown. Whew! Thank God! I was afraid I was gonna have do another drag scene, like in "Leisure Suit Larry 2 & 3."

Then again Larry has listed occasional cross-dressing as one of his hobbies, so perhaps he is a closet transvestite (he just chooses not to identify as the latter, and seems to be fine with being called a 'cross-dresser').


 * He's a cross-dresser. You'll never believe what he did with my show outfit.

Behind the scenes
Humorously Larry crossdresses in LSL2 and LSL3 he 'appears' have full breasts and everything though he stuffs out with 'soap' in LSL2 to make them look more full (but it does give him pretty 'accurate' looking boobs, comparable to those on the transvestite Shablee in LSL7, who also seemingly sports breasts under baggy clothing ).

A drag queen is a person, usually male, who dresses in clothing of the opposite sex and often acts with exaggerated femininity and in feminine gender roles which is for the purpose of entertainment.

Drag is simply wearing clothes of another sex (a 'drag queen' does it as entertainment). It does not mean that the person identifies as another gender. Nor does it mean the person gets sexual pleasure off of wearing the clothing which is one of the definitions of transvestite. Nor should it be confused with transsexual someone who does identify as another gender emotionally and psychologically (often going as far to permanently alter themselves).