Hailey Bieber knows how to transform a basic outfit with an impeccable sneaker choice. She frequently opts for supermodel staples like the Bella Hadid-favored Adidas Sambas or limited-edition New Balances. This week, she married sporty track pants and a $1,950 Miu Miu bag with the help of another classic lace-up in her arsenal: the Asics Gel Kayano 14s.

I feel especially qualified to speak on this topic because I’ve been wearing these trainers for years, collecting new iterations the way a museum acquires art.  While the new Kayano 29s are a fabulous running shoe, nothing quite captures that laid-back, Y2K-vibe like the Kayano 14s. Adorned with the brand’s instantly-recognizable stripe, they have the quintessential dad-shoe silhouette that adds a playfully ironic touch to otherwise trendy looks, and figures in the fashion industry can’t get enough. I wear my own pair with everything — leggings, blazers, maxi skirts, you name it — and they never fail to garner compliments. 

Shop now: $150; jcrew.com, urbanoutfitters.com, net-a-porter.com

Shop now: $150; jcrew.com, urbanoutfitters.com

During the 2023 fashion week, these sneakers were particularly life-saving. The end of the busy week fell on my birthday, which meant hours of walking between events and hours of dancing on my feet. In total, I walked 13 miles in one day, but they kept me incredibly comfortable through the chaos. Originally developed for running, the Gel-Kayano 14s feature layers of plush cushioning on the sole that cradles your arch and protects your legs from impact. In short, each shoe feels like a mini mattress for your foot. 

Shop now: $140; urbanoutfitters.com

The only downside to this throwback style is that it can be incredibly difficult to find online. Because of its recent resurgence, the pair sells out constantly, but is currently available at Urban Outfitters and J.Crew. A few rare colors are even on sale at luxury fashion retailer, Ssense. Like my own pair, most of these in-stock pairs are listed in men’s sizes, but I find mine to fit perfectly on my women’s size 9 feet. With this in mind, if you’re considering an investment in this iconic sneaker, I suggest you add it to your cart ASAP. 

Shop now: $117; ssense.com

Shop now: $117; ssense.com

Shop now: $113; ssense.com