"Shout-out to my dad, he influenced my style when I was 17," Theophilus says in the episode airing Saturday at 11 a.m. ET/PT.
"I was introducing him to be swag," his father, Moses, says. "You have to be crisp, you got to be clean. You got to be ready for school," the man behind Theophilus' exceptional style recalls advising his son.
While Theophilus didn't have a big spending budget, he found creative ways to get the looks he wanted, and that included hitting up his dad's very hip closet.
"I didn't have that much money, so I'd wake up in the morning and raid my dad's closet," he explains. "He had all the freshest Jordans, and he never wore his Jordans, so I was like, 'Man, somebody needs to wear them.' " Of course, he made sure not to nick the kicks.
Fans got to see firsthand just how the rapper uses his eye for fashion to make the ladies swoon when MTV News' Rya Backer took Theophilus on a First Date to a vintage thrift store. But even back in the day, the NYC rapper was trying to make the girls' heads turn. "My clothes [on] Sunday would be picked out for the week: This is Monday, this is Tuesday; this girl is gonna like my outfit on Friday."
"When I Was 17" — this week featuring Amy Lee, Chris Klein and Theophilus London — airs on Saturday at 11 a.m. ET/PT on MTV.