Yes, Dear (2000)

S4E11 Pimpin' Ain't Easy

Greg forces a reluctant Kim to accompany Mr. Savitsky as his "escort" to an art exhibition, but his mood shifts when Kim finds her own motivation to keep up the ruse. Meanwhile, Logan discovers that all of his clothing was previously owned by Dominic and reacts by staging a protest against the hand-me-downs—venturing around town in just his tighty whities.