Taylor Swift Introduces Gigi Hadid to Winter’s Square-Toe Boot Trend

Sounds convincing enough to me. But such is the hysteria that gathers around this Billboard bulldozer: everything Swift does, or seemingly doesn’t do, is treated as a clue into her past and future projects. I wonder, then, what last night’s look was meant to signal: a peacoat (millennial vindication), a pleated miniskirt (the coming-of-age anxieties she still mines as a 35-year-old billionaire), snakeskin knee-highs (the yet-to-be-announced release of Reputation (Taylor’s Version). For some, the message will be as blunt as the right angles of those Stella McCartney squared-toe boots.

Whether the sight of Swift—who was photographed beside Gigi Hadid while en route to New York’s Zero Bond in a coordinating dark velvet coat, leather trousers and polka-dot top—will kick-start a moment for quadrilateral boots is as speculative as the easter-egg theories. Arguably for some they are already there: even a cursory scroll through the fall 2025 shows suggests the once-derided horizontal toe (Balenciaga, Martine Rose, anyone?) is already mid-rehab via Miu Miu, Chloé, Chanel. If Swift can be retro-fitted into the 1980s, then beaming square-toed boots into the future should be light work.