Highsnobiety
Double Tap to Zoom

Few things say New York hip-hop culture more than a pair of Timberland's 6-Inch boots.

Initially designed as a sturdy piece of workwear, the classic yellow suede boot's sturdy construction found fans far beyond the construction site — especially in NY.

While the city's rap scene blew up, the boots were on the feet of everyone from Tupac to Aaliyah, name-dropped in Biggie's lyrics, found on Mobb Deep's album covers, and if you fast forward to the early 2000s you'll even find Cam'Ron decked out in an all-pink pair.

In true 90s fashion, you would find the shoes almost exclusively worn with an extremely baggy pair of jeans. But what do you do if you want to wear "The Original Yellow Boot" during the warmer months? Switch the jeans for baggy jorts, of course.

Two cornerstones of 90s hip-hop fashion, combine them and you have a look that's deeply entrenched in New York's history.

And as the boot celebrates its 50th anniversary, there are few better ways to honor it than to also bring out the baggiest pair of jeans shorts imaginable — just as many of New York's current rappers have done.

Most notably, New York's very own A$AP Mob has been leading the charge with Rocky's dollar-sign-covered look up above, A$AP Ferg and his super long jean shorts down below, and A$AP Nast's matching jacket and shorts (although, on closer inspection, Nast's baggy shorts are a leather pair from GUESS USA).

Your Highsnobiety privacy settings have blocked this Instagram post.

But it isn't just New York natives who have been trying out the unconventional pairing, nor is it just rappers.

Lil Yachty, whose style credentials have been criminally underrated, was even wearing shorts and Timberland's on the beach when he recently interviewed Drake.

Plus, you've got the NBA's best-dressed player, Shai Gilgeous-Alexander, wearing the classic yellow version of the boots with Louis Vuitton monogrammed denim and a GUESS USA leather jacket for a take on the look that's way out of my budget.

Your Highsnobiety privacy settings have blocked this Instagram post.

Since we've already added baggy jorts to our summer wishlist, thanks in large part to Amelia Gray Hamlin, it looks like it's time to find some matching Timbs.

We Recommend
  • First, Bottega Veneta Made Its Own Timbs. Now, Timberland Made Its Own Bottegas
    • Sneakers
  • You've Never Heard of New York's Coolest New Fragrance Store (EXCLUSIVE)
    • Beauty
  • At Last, Big Boot Season Is Finally Here
    • Style
  • Veneda Carter’s Glossed-up Timbs Just Got a Lot Shinier
    • Sneakers
  • Timberland Inflated Its Timeless Boot (& Added Luscious Leather!)
    • Sneakers
What To Read Next
  • COMME des GARÇONS' Reflective Nike Sneaker Just Makes "Sense"
    • Sneakers
  • The World's Best Band Tees Are Back, In Exhaustive Detail
    • Style
  • Telfar Infinity: Where Necklines Are for Legs & Armholes Are for Heads
    • Style
  • Nike's Pretty (& Glossy) "Hydrangeas" Air Force 1s Are in Full Bloom
    • Sneakers
  • Nike's "Donkey Kong"-Themed Air Maxes Are Pure Swoosh Genius
    • Sneakers
  • A Grass Green Fred Perry Polo Shirt, Dyed With Actual Grass
    • Style