Hailey Bieber Just Wore Her Cropped Jeans With Heeled Flip-Flops

By Swedan MargenMay 15, 2026

After what’s felt like a never-ending month of weather whiplash here in the UK, I bring good news; it’s finally set to warm up over the next few weeks. And although I'm excited to get out my breezy linen trousers and floaty midi dresses for the season ahead, I can guarantee you that you’ll find me in jeans more often than not. Come rain, wind, or (hopefully soon) sunshine, my trusty pair of cropped jeans will be my first port of call on those days when I’m stuck on what to wear. But with this comes a dilemma I’m sure we’ve all encountered: which shoes shall I wear with them?

Now, you might initially be expecting me to say trainers or loafers, but with sandal season soon on its way, chic dressers have found a different summer shoe trend to wear with their cropped jeans, and it’s effortlessly cool. Enter the heeled flip-flop trend.

Hailey Bieber wearing cropped jeans and flip-flops in Beverly Hills (13/05/2026)

Most recently, I spotted Hailey Bieber styling her cropped jeans with a pair of kitten heel flip-flops, a black V-neck tee and a cream car coat, creating a street style look that balanced casual comfort with effortless elegance. The heeled flip-flop trend combines the relaxed appeal of classic flip-flops with all the sophistication of a kitten heel, providing an easy way to dress up your cropped jeans whilst maintaining comfort. Not to mention that if you’re a petite fashion person, the height of the sandal will help to keep hemlines from skimming the ground.

As a flat-shoe-lover myself, I was initially quite sceptical of trying out the trend. But rest assured that the walkable heel height plus the support from the straps make this elegant sandal style the perfect introduction for those of us who aren’t used to wearing heels. Keep scrolling to shop the best cropped jeans and heeled flip-flops to invest in for summer 2026 and beyond.