The men of Leonida, read by their clothes: Jason, Brian, Cal, Boobie, Dre'Quan, Raul and the bikers
Ruby did the women of Leonida with Eve. Now the men: what each of Rockstar's named characters wears in the official screenshots, and what the clothes say about the job each one wants you to believe he has.

My thesis, up front: every man Rockstar has named dresses for the job he wants you to think he has, not the one he does. The facts below are what the official screenshots and bios show. The readings are mine, and I will mark them.
I'm Ruby. Last week Eve and I did the women of Leonida, she read the people and I read the clothes. The men deserve the same treatment, and they are easier, because men in a Rockstar game dress like a job description.
Jason Duval: the uniform he chose instead
Confirmed. Tank tops, cargo shorts, a chain, a leather jacket. Tattoos on show, including a full back piece in the Electric Fang Tattoo shots. The pre-order pack adds a pastel suit and period hair.
My read. This is a man who had a uniform and gave it back. Everything Jason wears now is the opposite of issued: loose, cheap, chosen for heat and boats, nothing that needs ironing. The chain is the one vanity. The back piece is the one commitment, because it is the only thing he owns that he cannot take off. Eve has his whole story today; I would add that the pastel suit in the pre-order pack is the first time he will look like he is trying, and I want to see his face in it.
Brian Heder: camouflage
Confirmed. Faded shirts and a cap. A veteran smuggler who moves product through his boatyard.
My read. The oldest trick in the Keys: dress like the thing you are pretending to be. A man carrying product looks like a man carrying bait. Brian's clothes are not a style, they are a cover story that has worked for thirty years, and the fading is part of it. New clothes get noticed on a dock.
Cal Hampton: the hat
Confirmed. A bucket hat, indoors, with radios. Rockstar's whole description is a man who feels safest at home listening to police and Coast Guard chatter.
My read. A bucket hat worn inside is the clothing equivalent of never taking your coat off at a party. Cal is dressed to leave and never does. It is the most honest outfit in the game.
Boobie Ike: ownership
Confirmed. A bold printed shirt open at the collar, heavy chains and a watch. Real estate, a strip club and a recording studio.
My read. This is established money, and it dresses like it has nothing to prove and everything to protect. The print is loud so you look at the shirt and not the business. Compare him with the next man down the org chart.
Dre'Quan Priest: access
Confirmed. Oversized tees, a red varsity-style jacket, a cap, a phone in his hand. He books acts at Boobie's club and runs Only Raw Records.
My read. The middleman's uniform: young enough for the talent, harmless enough for the money. A varsity jacket is a costume of belonging, and Dre'Quan has not quite decided which team. Put him next to Boobie in the same club shot and the dress code is the hierarchy.
Raul Bautista: the legitimate businessman
Confirmed. A white suit over an open shirt, a plain watch, grey at the temples. A seasoned bank robber who recruits risk-takers and whose recklessness raises the stakes.
My read. The best-dressed man in Leonida, and the most dangerous for it. A white suit says I have never had to run. The open shirt says I am relaxed. The plain watch says I do not need to show you. All three are lies, and they are the lies that get Jason and Lucia on his crew. If clothes are a police lead, Raul has worked out that the trick is to look like the man they would never stop.
The Ambrosia bikers and the Port Gellhorn men: no costume at all
Confirmed. In Ambrosia, a column of bikers in leather cuts riding two abreast. In Port Gellhorn, shirtless men with full-torso tattoos, a backyard wrestling ring, a fist fight outside a motel. Rockstar's description of the town runs on cheap liquor and energy drinks.
My read. These are the two ends of the state where nobody is pretending. The cut is a uniform that says exactly what it means. The bare torso says there is nothing left to hide behind. Between them, in Vice City, everybody else is in costume.
Why it matters in play
Confirmed. The police track what you wear as one of their leads, and a complete change of outfit clears it. Reported (Edge). People react to what you carry. My advice: when you dress Jason, decide which of these men he is impersonating that day. A getaway in Raul's white suit is a bad idea. A getaway in Brian's faded shirt is a plan.
The characters wiki has every confirmed fact, and the Only Raw Records page has the whole Vice City circle. The readings, as ever, are mine.
Quick answers
What does Jason wear in GTA 6?
In Rockstar's screenshots: tank tops, cargo shorts, a chain and a leather jacket, with tattoos on show including a full back piece. The pre-order Vintage Vice City Pack adds a pastel suit and period hairstyles.
What does Raul Bautista wear in GTA 6?
A white suit over an open shirt and a plain watch, grey at the temples. Rockstar describes him as a seasoned bank robber who recruits risk-takers.
Do clothes matter in GTA 6?
Yes, in one confirmed way: the police track your outfit as one of their leads, and a full change clears it. Edge reports people also react to what you carry.
Sources: Rockstar Games: Grand Theft Auto VI (character bios and screenshots) · SixStarsWanted wiki: characters · SixStarsWanted: the women of Leonida, read two ways
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