M: So, my first memory with Timberland is actually all the way back in sixth grade with my dad, who took me to get my first 6-Inch Boots. That was just meant to be a practical winter boot, but I fell in love with the shoe. Ever since then, I’ve bought it on my own because it already had such an iconic status in everything I was consuming through hip-hop culture. I mean, all of my icons - like Das EFX, Wu-Tang Clan, Mobb Deep, The Notorious B.I.G. - I saw these boots come alive in a different way. So I definitely wanted to embody that. Yeah, it’s been a shoe that’s been with me my whole life, and I still have a deep passion and love for it.

S: My first memory with Timberland is when I was starting 9th grade, and my mom was taking me out shopping. I remember seeing the 6-Inch Boot and falling completely in love with it. The feeling it gave me - wearing those on my first day of school and how empowered I felt starting my first day - is something that I'll probably never forget.

S: I think depending on which pair of Timbs you want to wear and whether you want to style it up or down, make it more chic or more casual, it's a shoe that you can dress up and down in whatever way you want. But my go-to look would probably be a baggy pair of jeans and an oversized tee, maybe a little cute jacket. And yeah, that's probably it.