Considering Work It brought to mind a 1999 episode of another ABC situation comedy, Dharma & Greg.
The title of the episode was "Dharma Drags Edward Out of Retirement" and it involves edrag.com, a company that merchandizes women's fashions for men.
In my humble opinion, this episode of Dharma & Greg handled crossdressing far more respectfully than Work It. It was humorous without throwing transwomen under the bus.
You can view the episode for yourself on YouTube, where it is in divided into three parts (1, 2, and 3).