When Timberland Had a Stranglehold on Hip-Hop

12 min readNov 10, 2023

Gather around boys and girls, hypebeast and hypebeastettes, Uncle Sadiq has a story to tell you. It’s a story that took place before there was a term applied to a person obsessed with sneakers. It’s a story that takes place at the infancy of what is now known as streetwear. A story that, due to the fact that it took place three decades ago, is one of legend.

This story is about when Timberland, a little New England company, dominated the feet of men, women, and children in the Hip-Hop community. It’s a story that touches on how things become trends–and, thanks to modern technology, is one that can be demonstrated with visual aids.

Some might call it nostalgia. But this ain’t that. This is just a good o’ tale about how we took a shoe designed to withstand winter in the arctic and made it streetwear. This is history.

We Ain’t Do It First

I don’t know how the conversation started.

One time I was conversing with my close friend from Genoa — the topic — Timberlands. She said they were wearing the boots back in the 80s. I had never heard of such a thing. The year was 2009 and my search didn’t yield many results. Then she gave me a name — Paninari — I at least got a photo.

A group of Italian youth in bright Moncler puffer coats, jeans rolled up above the ankle, and on the feet of five of them — the infamous Timberland Yellow Boot, the brand’s flagship boot — the others wore the 3-Eye Lug Handsewns (Timberland’s answer to the Sperry boat shoe).

I was at sixes and sevens.

That image of the Paninari was from the 80s. The 80s? You mean back when the average B-Boy and B-Girl was wearing Pumas or Adidas? You mean in the days of Lee, Le Tigres, Cazals, Bomber Coats and what not? I replayed the first time that I saw the Yellow Boot. It was during that era. Timberland were popular indeed. But not with us.

In 1984 I was attending Northern Burlington Middle School in Mansfield Township, New Jersey. It’s the school that military kids of McGuire AFB and Fort Dix attended. And it was in the country. It was at-the-end-of-October-we-had-a-day-off-for-the-beginning-of-hunting-season country The kids that were doing the hunting — they were the ones that wore the Yellow Boot.

Meanwhile, behind the closed doors of Timberland, a civil war was taking place. It was a war between sales and marketing. The sales side believed that making affordable shoes was the way to go. When the Yellow Boot was created in 1973, it was originally sold in Army-Navy surplus stores. It was a functional boot. That was the easy, simple route. Marketing, on the other hand, believed that the company should double down on raising the price of the boots and selling to high-end vendors. Their argument was based on the Paninari..

Over the past six or seven years there’s been more written about the Paninari. They’ve been dubbed the first hypebeast, the originators of fast food in fashion, but when pulling up articles from the 80s, they were spoken of as bored, privileged youth that acted like gangs. Italian newspaper la Repubblica sounded all sociological-like when they stated:

“the “paninari” gathered in about ten gangs, scattered in the historic center, where they are stationed, delimiting their “territory” and provoking some passers-by, looking for the dispute. All, or almost all, children of the good Milanese bourgeoisie, in search of the reckless life and strong emotions that the city is able to offer.”

Fox Butterfield, in an article titled ‘Shoes That Sell — Made In America,’ mentioned how these same Milanese teens “instead of robbing people for money, the hoodlums strip them of their shoes — Timberland shoes, to be precise.” They were spoken of as having weapons and battles, and they ate (GASP) fast food. For almost ten years, Paninari culture was the youth culture of Italy. There were magazines. There were movies centered around these teens. And it was all orchestrated by one man — Giorgio Faccioli.

Faccioli was that dude. Armed with twenty years of importing experience, he was confident. What he imported was foreign cool (he started importing Clarks into Italy in the 50s), and was confident that he could make anything stick. Why? He was a salesman. And what he sold — the psychology of exclusivity.

The owners of Timberland, Herman and Sidney Swartz, had no idea .

Italy was the home of luxury brands like Gucci and Ferragamo, how was Faccioli going to sell them big, bulky “lumberjack” shoes?

“I identify an eccentric, almost ugly, but very recognizable item of clothing or accessory. I give it to famous people begging them to wear it. I put it up for sale at a stratospheric price. And within a few months it becomes a status symbol,” Professor Salvatore Casillo, founder of the Museo del Fasio (a museum dedicated to the study of forgery), recalled Faccioli explaining to him.

And that’s what Faccioli did.

Faccioli got Timberlands on the feet of Gianni Agnelli, Enzo Biagi and Luca Cordero di Montezemolo. Timberland were even said to be on the feet of the Ferrari pit crew. With that, a trend began.

We had no idea what was going on 4,070 miles away. It was a revolutionary time for sneakers. And by the end of the 80s, the Paninari were gone. But as the 90s began, the same thing that worked on Italian youth would work on young Black men and women in America. The difference was, it was unintentional.

The Power of the Video

You might miss em.

It’s thirty four seconds into the b/w, Fab Five Freddy directed Gang Starr video “Just To Get a Rep.” A crew of brothas led by Lil Dap are walking towards the camera. They rock the uniform of the times: hoodies, baseball hats, baggy jeans and it’s almost like an ad for the 33hi, the Patrick Ewing signature shoe.. But one of the dudes doesn’t have on sneakers. If you blink, you’ll miss em.

I didn’t blink.

Which is why thirty years removed from the maroon leather seats of Morehouse’s Frederick Douglas Commons where we caught our music videos, I can remember the first time I saw em. Camera left, stage right, one of the brothas had on a pair of 40 Belows. But it was before the days of the internet. There was no way to find out what those boots were. Nor was there a way to explain a split second in a music video. This was college. No one was making tapes of videos. You saw that video once a day. Maybe.

Something could be bubbling up in another part of the nation and you would never know about it. So whether the Timberland Super Boot was gaining traction in the Northeast that winter of 1990, not only were they not showing up in music videos en-mass, they weren’t in ads or on many feet. Two years later, that would be different.

He had to talk himself into the movie.

Tupac wasn’t the first choice but he had been preparing himself for this moment his whole life. Having found solace in acting first and later rap, Tupac had the muscle memory to tap into a role and after his audition, casting director Jaki Brown knew he was perfect.

Whether it was costume designer Donna Berwick or Tupac’s idea, Juice (1992) was the second time I recall seeing one of the most coveted models of the Timberland catalog, the 40 Below Super Boot. The movie was shot between March and April of 1991 and Director Ernest Dickerson had to have an idea of the significance of the boots because he made it a point to have cinematographer Larry Banks open up a shot on em, panning up to a swagful Pac. After the movie was released, there would be two legends–Pac and them Timbs.

Charlamagne Tha God wrote about how he was impacted by seeing the Tupac x Timb connection saying, “when Juice came out everyone talked about how fly Tupac looked when he tucked a .38 pistol into his 40 Below Timberland boots. So of course me and my boys also wanted .38s and Timbs…”

I ain’t want a .38. But I absolutely wanted those 40 Belows.

When I saw that “They Want EFX” video, I just had one question, “where do you get em?”

As spring rolled into summer, the videos were coming thick and fast. Ultramagnetic’s “Poppa Large” had a straight jacketed Kool Keith spinning around in a chair, shorts…and Timberland. Other shots of the MCs had them slow motion walking booted up (the Michael Lavine shot Funk Your Head Up album cover had everyone but Keith in the 40 Belows). Seeing the Timberland that CL Smooth rocked (“They Reminisce Over You”) with that leather hooded coat convinced me — I was getting some.

Not from Foot Locker. Not from Macy’s. Not even the average Sporting Goods store carried them. That went back to the Swartz’s decision to sell to exclusive retailers. I was in Denver that summer and the only place to get Timbs was Larry’s Shoes on 403 East 2nd Street in the Cherry Creek neighborhood. Translation: Affluent. We stumbled on the place headed to the mall and became fervent customers.

They ain’t have the 40 Belows but they had other 10” high boots and I copped some (a part of the Timberland Sports Series). Yes, in the summertime. Yes, I wore them with shorts. Yes, religiously. And I wasn’t alone. My boy Sayyed actually DID get the Super Boot, and our brother Elam had him a pair of Timbs as well. That, and us being Five Percenters had the Rollin’ 30 and Hoover Crips calling us “the New York N*@&s.”

Which also has to be stressed — I can’t speak about the rest of the nation. But for all New York-centered Hip-Hoppers, Rap was in the last days of danceable music. 1992 would be the height of so-called Hip-Hop dance where crews still “caught wreck.” It was also the end of the 10” high boot dominance. But that’s ok. Because once 1993 rolled around, we tapped into a wider variety of the Timberland catalog.

Hip Hop Makes a Shift, So Do The Shoes

The West Coast had been filling morgues with fictional murders since the late 80s — it’s why their music was dubbed “Gangster Rap,” but New York influenced music had held out. Despite early tales of crime by Schooly D, KRS One, and Just-Ice, it was uncommon to hear lyrics geared towards beatdowns and homicide.

But that was soon to change.

Naughty by Nature led the pack. Sure, they had party songs and used familiar and friendly samples for some of their tracks. But cuts like “Guard Your Grill” and “Pin the Tail on the Donkey” were a forecast of what was to come. Something else was prophetic about Naughty as well — their choice of clothing.

While most New York influenced rappers wore bright colored Champion sweatshirts, Cross Colours, Polo and to a lesser degree Tommy Hilfiger, Naughty by Nature — specifically Treach donned “Timber boots” (Black Chukkas) and “jail suits” (Dickies) and rapped about it in “Uptown Anthem.”. It was no-nonsense apparel that writers love to attribute to hustling. Workwear was Naughty’s norm. Carhartt and army certified jackets and coats were the uniform. Affordable. Drab. The same look can be seen in Kool G Rap’s late 1992 video “Ill Street Blues.” In that Lionel C. Martin directed clip, Kool G Rap’s wardrobe consists of alternating Black and Green M65 Field Jackets and matching Patrol Hats.

The only 10” high Timberland that could go with that would be black. As a result, the Chukka became popular. Whether maroon or black, that boot began popping up everywhere as New York-centered Rap took a turn towards “reality.”

Fat Joe’s “Flow Joe” is a good time capsule for that turn. Apache’s “Gangsta Bitch” name checked Carhartt and featured the brand throughout the video. Also featured were the 6” black Timberland. Them jawns damn near looked like military boots.

Onyx “Throw Ya Gunz” video is as good as an advertisement there is for that style of boot. Whole armies of bald-headed men run over mounds of sand in baggy jeans and Timbs while Fredro Starr, Big DS, and Sticky Fingaz yell at us. Being that this was Jam Master Jay’s group and because he was the one that was behind the original look of Run DMC, it makes sense that soon even they would appear as such — bald-headed, army suited, and Black Timb booted in “Down With King.”

While some of us took to the all-black look, others wanted to keep it brown. This is where the Euro-Hiker and the Field Boot (bka beef and broccoli/mac and cheese) Timberlands come in. These were boots that could be worn with any outfit, were unobtrusive, and boy were they ever-present. The Euro-Hiker may have been on more men and women per capita than any other Timb at the time, but the Field Boot was just as popular..

When Freaknic 1993 convened, Black men from far and wide rolled into Atlanta with the bald head+Black Timbs combo. That’s when I knew…this is a thing. Timberland became so popular, sneakers were no longer the shoe of the Hip-Hop head and the execs of the brand (and the

media) took notice.

Numbers don’t lie.

When your company’s net sales have increased by 46% (year to date), something has to be going on. And, imagine if you hadn’t done anything different in terms of marketing. Your company hasn’t released a new product that’s taken off either. What, you would have to ask, is the cause of this astronomical increase?

Those numbers got the media’s attention. Timberland had shown its highest quarterly revenues…ever, but when questioned about it by New York Times writer Michael Marriott in his now infamous Out of the Woods article, Jeffrey Swartz, then executive vice president of the company claimed the “urban market” didn’t even constitute 5% of those sales.

I won’t go into that bit here (Kierna Mayo did that in the December 1992 Source) just suffice it to say — nope. Brooklyn MC Masta Ace said in the same article that he knew teenagers who owned five or six pairs of Timberlands. It was me. I was teenagers. Well, I was no longer a teen, but I owned six pairs: the original Sports Series, black and maroon chukkas, oxfords, and two mesh-like pairs, one high, one low ​​(I’ve found it impossible to find the names of many of their boot lines).

And I wasn’t alone. Almost everyone I knew had a collection of Timbs. Sure some people incorporated the Vasque Sundowner or another style of Vasque boot into their arsenal but by and large it was Timberland. That dominance was reinforced with the rise of crews like the Boot Camp Clik in general and the Wu Tang Clan in particular.

Sneaker brands also recognized this and scrambled to come up with their own boot equivalents. Reebok had the Telos, Nike dropped the Air Mada, Adidas gave us the Cross Trail Hiker, even Asics got in on the act with the Gel-Havoc. If you opened up a Source Magazine in these times, it would be full of boot ad after boot ad. The seasoned Source aficionados remember the Boots Style section which sometimes featured as many as sixteen brands: there was Simple, Merrell, Movade — there was Technica, Brigade, HH Brown, there were so many boots, and Timberland led the way.

The tipping point was 1994 when everyone from Popular Mechanic to the Toledo Blade were talking about the new boots “trend.”

Of course as things become popular, they begin to change. Now, you could go into Macy’s (or any department store) and pick up a pair of Timberland. The boots were in Foot Locker, Athlete’s Foot, Champs. They were everywhere. But the company couldn’t meet demand, profits were miniscule, which in turn made stocks drop from a high of $86 to $22 a share. And the company began introducing new lines….that didn’t necessarily connect with us.

I never got a new style after the StrataVarious Mids in 96.

The average New York-centered Hip Hop head stuck with the traditional models sans the Chukka. The Euro Hiker and the Field Boot stayed in play but it was that same boot that Italians fell for that would have the longest run. The Notorious B.I.G. might as well have been the brand ambassador. Whether it was photoshoots or videos like “Juicy” or Total’s “Can’t You See,” Biggie rep’d the Timberland flagship boot affectionately dubbed Constructs.

It could be added to any scenario to “street” things up. Yeah, Diddy and nem wore shiny suits — no question. But you were gonna see someone (Jadakiss) in them Constructs. Jagged Edge may have been some crooners…but they gonna woo the women in themYellow Boots. The Constructs found their way to model feet and back before Louboutin were the Black woman goto shoe of class and prestige, Manolo Blahnik reigned supreme. Homie made a pair of high heel Constructs that Jennifer Lopez wore at the height of her powers (the same high heels that resurfaced when a certain Kardashian donned em).

The Yellow Boot became synonymous with all things New York. Jay-Z picked up the Construct mantle that Biggie once held and carried the boot into the new millennium. The Diplomats rocked em. State Property wore em. Nelly was a fan. DMX said that he owned up to 1,500 pairs. It was a staple. But as the aughts progressed, boot wearing waned in general, and Timberland’s dominance faded in particular. Every once in a while someone like Kanye would have a nostalgic moment and throw on a pair but as far as Hip-Hop heads buying them en masse, those days were over.

Even New Yorkers switched allegiance to the Nike Air Max Goadome.

The void left by boot popularity was filled by a movement that was practically underground and unnoticed until February 23rd 2005. But that’s another story for another day, boys and girls.