The ‘Toothpick Rule' and Other Tips for Wearing Bootcut Jeans in 2025
In the Y2K days of pagers and landlines, bootcut jeans were the de rigueur uniform of angsty teenage mall rats. Though the capacious denim style eventually went dormant, it has reawoken in 2025. Prominent fans include actress Sydney Sweeney, model-turned-mogul Cindy Crawford and most notably Kendrick Lamar, who donned a pair during his Super Bowl halftime performance this February.
After Lamar wore them, 'they officially went mainstream,' said Meredith Melling, the co-founder of New York clothing brand La Ligne. As she put it, many women felt an urge to 'get on board.' And they did. Google searches for bootcut and flared jeans skyrocketed by 5,000% within 48 hours of Lamar's swishing performance.
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