Clue: Five he-men stripped into skimpy underwear by the roadside? (8)
Answer: PAVEMENT
Explanation: Definition: roadside
 [ V(Roman numeral for "five") + "he-men" **minus its 1st and last letters**(stripped) ] **contained in**(into) "pants"(underwear, specifically underpants or knickers) ***minus its last letter***(skimpy …).
Defn: A … that has been raised and paved for pedestrians.