The Coolest Shoes to Wear With Flared Trousers in 2025, According to a Gen-Z Fashion Editor

Over the past few years, flares have transitioned from a ‘dated’ fashion relic to a chic and contemporary style staple. Kick-flare jeans, flared leggings and tailored black versions crop up constantly in the trendiest corners of Instagram and TikTok, proving the endless versatility of this rediscovered classic.

But if you’re not used to wearing flared trousers, they can be difficult to style the first time around. Especially where footwear is concerned. The wide silhouette of flares can make choosing the right shoes a challenge; you’re working with a different proportions, and the wrong choice could throw off the balance of your outfit. Luckily, though, some of our favourite influencers have mastered styling this 2025 essential, so we looked to them for guidance on which shoes to wear with flared trousers.