Product/Service:
Clothing
Real-Life Business:
New Era Cap Company
Seen:
Trailer 2: 1:59
Watch
Old Gen is a clothing company that appears in GTA 6.
The brand made its first appearance in GTA 5, where it was featured on a variety of clothes, in particular headwear.
Old Gen is best known as a hat designer, though it also manufactures other clothing, such as T-shirts, jeans, and shoes.
In GTA 6 Trailer 2, 
Old Gen is likely to be a reference to the real New Era Cap Company, as the two brands have extremely similar logos. In addition, Old Gen(eration) is likely a play on 'New Era.'
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