The pillbox hat trend isn't going anywhere—Jackie O is still very much the poster child of old-yet-new style in 2026. (Opera gloves, capes, dainty watches —need we go on?) Since gaining popularity over the summer, there's been an even bigger return to polite society this winter. Ingrid Edvinsen wears a brown suede trench coat, black cashmere knit, black leather boots and handbag, and lastly, a black pillbox hat. Pillbox hats became popular during the 1930s, thanks in part to American First Lady Jacqueline Kennedy, who is considered a fashion icon and the epitome of. Originally a military style, it went through a transformation in the 1930s, shedding its service roots and taking on the sleek, stylish interpretation we know today. It wasn't until the 1960s, however, that the pillbox hat truly came into its own. New-season styles. Cynthia Erivo isn't the only celebrity to embrace the Jackie Kennedy-reminiscent style lately.
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