NO GARMENT embodies the trashy early 2000s more than the mesh-backed trucker hat. In 2003 alone, Paris Hilton and Nicole Richie appeared on their reality-TV show “The Simple Life” in orange camo Von Dutch trucker hats; a 25-year-old Ashton Kutcher sat courtside at a Knicks game in an intentionally askew trucker hat that read “Teenage Millionaire”; and Justin Timberlake wore one referencing the notorious infomercial empire “Girls Gone Wild.”

Trucker hats—their bulbous crowns as puffy as a microwaved marshmallow—became reviled by the late-aughts, when Hollywood stars who had come of age during the trend’s peak shed their juvenile “sleazecore” look. In 2020, however, as a new wave of dressed-down, sweatpants-heavy celebrity-endorsed fashion is surging, so too is the trucker hat. Pop culture fixtures from Hugh Jackman to A$AP Rocky to Justin Beiber have been snapped in trucker hats. Amiri and Rhude, two rising Los Angeles fashion labels, peddle truckers at $290 and $165, respectively. Ice Cream, the skatewear brand that Pharrell Williams started in 2004, has reissued some of its logoed truckers from the aughts.

Source: https://www.wsj.com/articles/trucker-hats-a-questionable-2000s-fashion-trend-returns-11606154175