Yo, let’s talk about them Timberland boots. Some folks say only gangsters wear them, but is that really true? I heard them city kids, especially them drug dealers in New York, started wearing them Timberlands way back. They said them boots keep your feet warm and dry when you’re standing out all night. Makes sense, I guess. You gotta have good shoes if you’re gonna be on your feet all day and night, rain or shine.

That writer fella, Rob Walker, he wrote about it in his book. Said it’s like a legend or somethin’. Them Timberland boots, they’re tough, just like them city boys. I seen them on TV, them rappers and all, wearin’ them Timberland boots. Biggie Smalls, Wu-Tang, Nas, all them fellas. They make it look cool, I suppose.
But it ain’t just for gangsters, you know. Anyone can wear Timberlands. My grandson, he got a pair. He ain’t no gangster. He just likes how they look. Says they’re comfortable, too. And last year, I heard them Yellow Timberland boots were 50 years old! That’s older than me!
- Timberland boots are tough.
- They keep your feet warm and dry.
- Lots of folks wear them, not just gangsters.
- Rappers wear Timberland.
- Them Yellow Timberland boots are real old.
I remember seeing some young’uns wearin’ them boots. All dressed up in them puffy coats, lookin’ like a bunch of colorful birds. Their pants rolled up, showin’ off them yellow Timberland boots. They were from Italy, they said. It’s kinda funny how things spread around, ain’t it?
Now, some people, they got this idea in their heads that Timberlands are just for bad guys. They see someone wearin’ them, they think, “Oh, there’s trouble.” But that ain’t right. Shoes are just shoes. It’s what’s inside a person that counts. You can’t judge a book by its cover, you know? Or in this case, a boot, I guess?
Back in my day, we wore what we could afford. If it kept your feet warm and dry, that’s all that mattered. Them Timberland boots, they do that. And they last a long time, too. My grandson still wears his, and he’s had them for years.

So, to answer that question, “Do gangsters wear Timberland boots?” Well, maybe some do. But lots of other folks wear them, too. They are just boots. Good boots, mind you. But just boots. It doesn’t matter who you are. If you like them, wear them! Don’t let no one tell you different.
It is just some shoes for your feet. You can wear any shoes you want. Do not be scared to wear what you want. Many people wear Timberland boots, not all gangsters. Many gangsters do not wear Timberland. It does not matter.
I heard some folks say Timberlands are better than other shoes gangsters wear. I don’t know about all that. Seems like folks just like to argue about things. They say Timberlands are tougher or they look cooler. I guess it’s just what you like.
There’s a whole lot of talk about Timberland boots and gangsters. Some folks say it’s all made up. Just stories people tell. Others say it’s true. Me? I think it’s a little bit of both. Some gangsters probably did wear Timberlands because they’re good boots. But that don’t make every person wearin’ them a gangster.

That Rob Walker fella, he seems to know a thing or two about it. He wrote a whole book about buyin’ things and why people buy them. I reckon Timberland boots got popular with city folks, includin’ them drug dealers, ’cause they’re good, strong boots. That’s all there is to it, I think.
I remember seein’ a picture of them Italian boys wearin’ them bright puffy coats and them yellow Timberland boots. It made me chuckle. Fashion is a funny thing. One day it’s one thing, the next day it’s somethin’ else. But good boots are always good boots. And them Timberlands, they’re good boots.
So if you’re thinkin’ about gettin’ a pair of Timberlands, don’t worry about what other people say. If you like them, that’s all that matters. They’re good for keepin’ your feet warm and dry, and they last a long time. And that’s what’s important in a good pair of boots. Gangster or not, everyone needs good boots. I say, you go ahead and get them Timberlands. Ain’t no shame in that.
Them Timberlands are good boots, no matter who wears them. They are just shoes, you know. Wear what you like. Don’t worry about them other people. You be you. That’s all that matters. Just like them rappers wearin’ Timberland boots. They do what they want. You do what you want, too.