Macklemore & Ryan Lewis -- Wing -

The song you're referring to is likely "Wing" by Macklemore & Ryan Lewis, featuring Hanzel. The song was released in 2011 as part of their debut studio album "The Language of My World" but actually appears on the "The Language of My World (Bonus Track Edition)" and also on the iTunes version of their album "The Heist" although not on standard track editions of either.

It transitions into a critique of how buying expensive shoes provides a fleeting sense of superiority and belonging, effectively turning the individual into a "product" of the brand. macklemore & ryan lewis -- wing

Faded vintage sneaker on left, a kid looking out a window on right. The song you're referring to is likely "Wing"

“They started out with what’s real / I can’t keep up with what I can’t afford.” Faded vintage sneaker on left, a kid looking

We spend money we don’t have to impress people we don’t like, chasing a “win” that never comes. And the saddest line?