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Olivia Rodrigo has become somewhat of an Anglophile in recent years. (As she said in a recent profile, “I love everything English, English culture and English people…”) So, it should come as no surprise that she stepped out in a quintessential ensemble that Londoners have been wearing for decades during a recent visit to the city.
Whilst promoting her third studio album, You Seem Pretty Sad for a Girl So in Love, the musician paid a visit to the Capital Radio studios wearing a silhouette that stylish denizens like Kate Moss, Sienna Miller and Victoria Beckham have all previously sported.
The look in question featured a floral-print Henley tank by Chemena Kamali for Chloe’s recent spring/summer 2026 collection—a panoply the singer has regularly worn, including during the Marie Antoinette-inspired music video for the record’s first lead single “Drop Dead”—a pair of black Levi’s jeans and the Coach Swing Zip bag. However, what piqued our interest most wasn’t this reliable outfit template, but the elevated shoe choice she paired these British staples with.
(Image credit: Backgrid UK)
Rather than embracing the romantic undertones of the botanical top by styling it with ballet flats or leaning into the edgy undertones of her cigarette trousers with a pair of sturdy boots, she eschewed both modes entirely by opting for a pair of chic pointed-toe heels.
For the uninitiated, the rise of the casual heel has slowly become one of the most defining summer shoe trends, with influential Los Angelinos like Devon Lee Carlson, Addison Rae and Hailey Bieber all opting for sky-high styles to complete their jeans looks. Given that Rodrigo herself is a California cool girl, it’s only fitting that she brings this trend across the pond whilst also paying homage to the British tastemakers that came before her.
As summer’s breezy climate invites us to slow down, unwind and wear fewer layers, enhancing your trusted denim styles with a sleek and elongating shoe choice feels not only sophisticated, but incredibly relevant. So, be it slingbacks, peep toes or pointed-toe heels, these inch-adding shapes will be the perfect complement to your arsenal of trusted stovepipes and straight-legs. All you need now is a pair of Y2K-inspired oversized sunglasses to pair it with…
Shop Cigarette Jeans and Pointed-Toe Heels:
AGOLDE
’90s Pinch Waist Long High-Rise Straight-Leg Jeans
M&S
Mid Heel Pointed Court Shoes
A staple of the high street for over a century, M&S can always be called upon for well-edited wardrobe basics.
H&M
Wide High Waist Jeans
For that off-duty effect.
These peeping out from the hemline of a pair of jeans will look so polished.
This cut has Parisienne appeal, too.
Ralph Lauren
Adrienne Leather Pump
This sweet heel length is so reminiscent of the The Row Liisa Heel.
Reformation
Val 90s Mid Rise Straight Jeans
Jeans and heels is such a fool-proof combination, despite its noughties connotations.
ZARA
Heeled Slingback Shoes
These chic mules add such dimension to a look.
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