Regarding cross-dressing comedies, I think that whether or not it works often depends on the strength of the cast. SOME LIKE IT HOT has a pretty good cast and while I don't agree with the many others who consider it the greatest comedy of all time, I think they're able to make it funny enough and do like the irony of the situations. Haven't seen TOOTSIE or GLEN OR GLENDA.
Regarding this short, I do think that it sort of works. Starting with the beginning, I'll note that one thing I really liked was the idea of breaking things in two, which is done both by Hardy's wife and by Laurel. With Hardy's wife, it's especially funny since she returns to the house specifically to do that.
Once it gets to Laurel in drag, particularly at the night club, I do like the dance that they do, mostly due to the energy that's put into it by Laurel and Hardy. While the gag of Hardy looking like he's undressing Laurel is a bit weird, I do like the reactions of the guy playing Hardy's uncle. That being said, the drunk guy is pretty annoying, though I'll admit that I laughed at the ending gag of him dumping his soup on top of Hardy, since they did it so late in the short. Hardy himself seemed to be slightly amused at the end, cracking a smile.
It's nothing spectacular, but I do think that this short makes for slightly amusing comedy. The only other interesting thing to note is that this was directed by Lloyd French, who directed some of Shemp's solo shorts and wrote AN ACHE IN EVERY STAKE.
7 out of 10