Over the years, this boot-wearing style may have slipped our minds, but it’s set to make a major comeback this winter. In the 80s, none other than Lady Di turned it into her signature look.
Endless Debates Among Fashionistas
There are timeless debates that stir the fashion world. To do or not to do? Fashion hit or fashion miss? Discussions about this style pairing have been heating up for months. This fall and winter, fashion insiders from Elle to the Nouvel Obs have explored this method of pairing two common wardrobe items. We’re talking about the combination of boots and trousers, a particularly suitable choice for the chilly season.
Though high boots have been somewhat out of the spotlight in recent years, often hidden under perfectly draped trousers showing only the tip of the shoe, they are now stepping out of the shadows. They are being boldly worn over jeans and trousers to revive a once-popular trend. Sophie Fontanel pinpoints its heyday in the 1970s: a notable fashion moment being when Diane Von Furstenberg was photographed alongside her husband, tucking flared trousers into snug knee-high boots.
However, the figure who made it her fashion trademark was Lady Di. During the 80s, the beloved princess enjoyed wearing her cowboy boots over a range of trousers, from fitted to baggy. This style of tucking trousers into boots was even dubbed the “Diana Tuck” by journalists at Elle UK.
Instagram and the Resurgence of a Trend
As the late 2010s brought about the resurgence of the Indie Sleaze movement, the “Trouser Tuck” ascended to the status of a trend to watch: Emily Ratajkowski, Kendall Jenner, and numerous fashion-forward individuals followed in Princess Diana’s footsteps, each offering their stylish takes.
While one might initially picture this trend with a pair of skinny jeans, it actually works with any trouser style: baggy, cargo, carrot, straight, flare, wide leg, and even joggers. The same stylistic versatility applies to the boots chosen: any style goes, as long as the boots are taller than ankle height!
One Fashion Risk to Possibly Avoid
There is, however, one sartorial gamble that’s a bit risky: rain boots. On TikTok, a user expressed her hesitation: “Oh my god, I would look like a fisherman from the coves,” she wrote. While Pinterest might predict a fisherman aesthetic as a key trend for the year 2025, mastering it to make the most out of the look is essential!
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Olivia Martinez is the Fashion Editor at Lady and The Track, bringing over seven years of experience in the fashion industry. With a background in fashion design and styling, Olivia has worked with top fashion brands and magazines. Her keen eye for trends and styling tips helps readers stay ahead of the fashion curve. Whether she’s covering runway shows or street style, Olivia ensures that Lady and The Track readers are always in the know when it comes to the latest in fashion.