Rocking Timberlands All Year Makes You the Definition of Fly

If you’ve ever worked the graveyard shift, you know you need an extra mental edge to get you out the door, much less to get you through the night. Your rituals take on added importance as a beacon of relative normalcy during a backwards existence.

When I worked as an overnight web editor during the winter of 2004-05, my routine was always the same: I’d wake up at 11:15 p.m., make oatmeal and green tea for “breakfast,” and throw on NasIllmatic while I steeled myself for the night ahead. When the clock struck midnight, I’d drag myself downstairs in the freezing cold to get on the last bus to New York City.

Illmatic had too many great lines to count; this one in particular became something of a personal mantra that winter. But it also resonated when Nas proclaimed, in an homage to KRS-1, that suede Timbs on his feet made his cipher complete. I kept Illmatic on repeat in my headphones every night during my 1 a.m. rides on the 1 Train, while I tried not to make eye contact with anyone.

Nas wasn’t the first MC to profess his appreciation for Timberland boots, and he wouldn’t be the last. But considering how revered Illmatic is–many consider it the best hip-hop album of all time–his tribute was perhaps the most memorable. (Biggie’s “black Timbs and black hoodies” also has a pretty strong case.) Whichever you prefer, the references show how far Timberlands had come from its purely utilitarian origins.

Originally designed in 1973 in New Hampshire, the Timberland was sturdy yet comfortable, perfect for all-day use by New England longshoremen and such. Timberland set itself apart with its development of injection-molding technology, a stitch-free way to affix the sole to the upper that made the boot pretty much completely waterproof.

I was an Air Jordan/Air Max fan as a kid, and before Nas set me straight, I had mainly perceived Timberlands as something my dad would wear to go hunting. That said, if their stated purpose was that they prepared you to weather any storm, their figurative role was much the same. Over time, they took on a completely new meaning; basically, to wear a pair of Timbs is less a fashion statement than a mission statement.

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“People said [in polling], ‘With Timberland boots on our feet we feel nothing can stop us,’” former chief executive Jeffrey Swartz told The Financial Times a few years back. “‘I live in a rugged world and I want to feel powerful and secure.’”

The company itself credits the Paninaro youth movement in Milan and hip-hop culture in Asia for helping to spread its gospel. Before long, the boots were a stateside sensation: Mobb Deep wore Timbs on the liner for the Infamous, Tupac did the same in the movie Juice, and George Costanza even bought a pair to make himself look taller on Seinfeld.

Though the basic work boot was still its bread and butter, Timberland eventually embraced its pop culture chops, collaborating with such entities as Pharrell Williams and Jeff Staple. At this point, Timbs have become as much a streetwear icon as all-white Uptowns or the black/red Air Jordan I.

“I mean, this is a company that is like a McDonald’s now. Every kid will have a pair of boots,” Raekwon of the Wu-Tang Clan told Champs Sports a few months ago. “They feel proud of wearing them, you know? They don’t take it for being a working boot. They’re made for you to tie up real tight and mess ‘em up. Not style ‘em and make ‘em stay crispy. It’s the opposite.”

How bulletproof had Timberlands become? Jay Z–who had more than enough influence to singlehandedly kill off throwback jerseys–wantonly took aim at the boots back in 2009 to no avail. That song was admittedly pretty lackluster for his usual standards, but even besides that, Timberland had close to 40 years of capital with the public at the time. Not to mention, its supreme functionality served to insulate against the transitory nature of fashion trends; ostensibly, people will always need a great pair of boots.

That, of course, goes for any season.

“Timberland boots used to be only be worn in the winter, but then people, such as myself, started wearing them all year ’round,” RZA told GQ last year. “I used to be one of the guys that other dudes would make jokes on when I would wear my Timberlands in the summer. … They had all the qualities of a good product and that’s why we continued to wear them.”

It will still be warm out when the six-inch Red Boot drops at Champs Sports this Saturday, but that doesn’t much matter: Timbs are well known for cooking up winter in the summer.

And long after I left behind the dead of night for the light of day, I maintain the utmost respect for how certain footwear can somewhat brighten even the darkest of scenarios.

Follow Bryan on Twitter at @sportsangle