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It's a holdover of a trend started in the 90s by drug-dealers in Oakland CA.
The flatbrim controversy has raged for two decades. But sideways wearers are generally considered to be douchebags.
I think maybe they know its a natural tendency for youth to rebel and if they are taught that being stupid is "rebellious" they are then not a threat to the crooked power structure.
Styles and fashion change, some times very quickly and sometime over time. Clothing has gotten progressively skimpier with less and less cloth going into the finished product over a period of years. Necklines are lower, sleeves are shorter, waistlines dropped, pockets shallower, etc. clothing fits more tightly to the body. This is especially true of women's clothing. This hass probably come about as manufacturers attempt to use less and less raw material in their finished product--as a means of reducing per unit cost. A lot of the fads and fashions in clothing have made their way up from sub-cultures e.g. prison and street attire, from the glorification in the mainstream of those cultures.
Even Mother Russia had them portrayed in about 5 yo comedy sketches (Nasha Russia comedy series)
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