The Street is streetwear that consists of a turquoise Hawaiian shirt, blue stone washed jeans and white sneakers based on the Adidas Superstar. Portions of the outfit are often incorporated into other outfits in GTA Vice City, such as glimpses of the Hawaiian shirt on the Coveralls, the jeans on the Casual and the Frankie, and the white sneakers on eight out of twelve outfits in the game.
The Street is the first outfit worn by Tommy Vercetti in the game, having been featured the entire duration of "In the Beginning...", between Tommy Vercetti's arrival to Vice City at Escobar International to Tommy's call to Sonny Forelli about the botched deal.
Although the Street is already worn, no clothing pickup for the outfit will be made available until the player completes "The Party" and obtains the Soiree, after which the pickup for the Street will appear in Tommy's suite at the Ocean View Hotel. It is assumed that prior to "The Party", there is initially no need for any clothes change due to the player normally having only one outfit (although the red variant Tracksuit is available from the start, it is not supposed to be accessible until after "Phnom Penh '86" but can be reached through exploits prior to the mission's completion).
The Street will also be made available at two more safehouses: The main office of the Vercetti Estate after "Rub Out", and the rooftop Hyman Condo after the purchase of the safehouse. If the player somehow manages to purchase the Hyman Condo before completing "The Party" by obtaining the money necessary for its purchase and using exploits or cheats to reach the mainland, the pickup will not appear until "The Party" is completed, while the game's tooltip will not mention the pickup being available at the condo as it is not adapted to deal with the premature purchase of the condo.
Changing into the outfit removes up to a two-star wanted level, even if the player is already wearing the outfit.
- Earlier pre-release screenshots featuring the player character in Street clothes depict its shirt in cyan, among other minor differences.
- Any mission that involves a mandatory clothes change halfway through will typically revert the player character's clothes to the Street in the beginning of the mission if he is wearing any other outfit.
- If the player character dies or is arrested, he will revert back to his Street outfit, regardless of which outfit he wears prior to his death or arrest.
- The Street character model in the PC version of GTA Vice City is the only one in the game to readily support custom skins.
- The design of the outfit is similar to Tony Montana's initial choice of clothing during his detention at a refugee camp in Scarface.
- Kent Paul's Hawaiian shirt in GTA Vice City uses a recolored texture of of the Street's shirt.
- Driv3r's Timmy Vermicelli's, who are supposed to parody Tommy Vercetti, base their attire on the Tommy's Street clothes.