There aren’t many shoes I wouldn’t wear with jeans. As someone who reaches for denim almost every day, I need my footwear to work hard alongside my favourite pairs. That said, for the longest time, rounded-toe heeled boots were one of the few pairs I wouldn’t consider. I could never quite put my finger on why, but when styled with denim, the softer silhouette always felt a little… dated. Less sharp, less impactful than some of my alternatives.

So I avoided the pairing—until recently, when suddenly, almost overnight, some of the chicest dressers I follow began styling their jeans with the very shoe trend I’d written off. I had to reconsider.

Just this weekend, Lila Moss finished her fruit-trimmed jacket and jeans with a sleek pair of black rounded-toe heels boots peaking out below her hem. Adding height and polish, the boots brought drama to her denim without tipping the look into overly dressy territory or clashing with the casual base.

Alexa Chung echoed a similar sentiment, styling her black cardigan and dungarees with, yes, another pair of rounded-toe boots. Where a pointed or square toe might have felt too sharp against the relaxed denim silhouette, Alexa’s choice felt perfectly balanced, lending softness and cohesion to the look.

Consider me converted. If, like me, you’ve been overlooking rounded-toe heeled boots for far too long, read on to discover and shop the chicest pairs to invest in now.

Shop Rounded-Toe Heeled Boots: