He's very good at looking a lot richer than he is. Growing up merchant class, you want to look well off even if you don't actually have the access to the finer things. It's about picking things that enhance the few actually nice things you have. As such, he's pretty picky about appearance—especially after he started trying to pick people up or be picked up in taverns and bars. Zharendiyan needed to stand out and look worth it.

716 AL (0) — Born to a merchant family in Ruatha Hold
720 AL (4)— Sickness sweeps through family, hitting his 2 older sisters, his father, and his grandfather. All by Zharendiyan's father die, and Zhenden's health remains poor. Working becomes very difficult for him.
723 AL (7) — Father commits suicide.
726 AL (10) — Jaryan remarries, another merchant named Shon, who takes over Zhenden's assets.
727 AL (11)— First younger half brother born.
729 AL (13)— Family moves to Sattle Hold for business. Shon sells Zhenden's tiny shop; Zh'yan is unhappy with this. He doesn't love the shop, but it's what remains of his father and was supposed to be his. In Sattle, Zharendiyan is expected to help raise and one day work for his younger half brother, who will inherent the shop Shon buys there—with the money from Zhenden's shop. Zharendiyan is, perhaps, a little bitter.
736 AL (20)— Shon and Jaryan try to arrange a marriage for Zharendiyan to the daughter of a steward. Her name is Mille, and she and Zharendiyan get along well enough. They fool around a bit while their parents are deliberating.
737 AL (21)— Jaryan dies, causes unknown. Zharendiyan takes it poorly and starts acting out. As a result, Mille's family decide he's a bad choice for their daughter and the potential betrothal falls through. Zharendiyan can't bring himself to care much. He starts doing things like getting into minor bar fights and sleeping around. One night a man offers to take him home, which Zharendiyan thinks sounds like a thing that would piss off his stepfather if Shon ever found out, so he accepts. Ends up being more fun than he expected. Hurrah for bisexuality.
739 AL (23)— Continues to be trouble at nights and barely a respectable worker at Shon's store during the day. Ends up falling into the bed of Keavos, the Lord Holder's younger brother (or, more accurately, a rented tavern bed, but whatever, semantics). Zharendiyan thinks it's particularly scandalous and while it's not like he's bragging about his gay exploits he still takes a smug pleasure in the shame it in theory brings to his stepfather. Keavos tracks him down a handful of times for sex, but stops by the end of the Turn (Zharendiyan thinks it has something to do with the fact Keavos called out someone else's name the last time, which like, that's rough buddy).
741 AL (25)— Searched for Fort Weyr by R'dal and Edath, which is actually pretty timely because Shon is about ready to take Measures about Zharendiyan and his wild ways.