Trucker Hats: A Questionable 2000s Fashion Trend Returns

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…

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