I can't say he dressed like a cholo at all and for the most part cholo's never wore Temberlands.. East coast Latinos wore them and it was an east coast style for the most part that drifted over in time (It was more a specific version of them also) .. His belt is also not a cholo style and more preppy. When someone 'sags' they tend to use 2 or so spots on their belts but not all. The way his clothes are baggy also don't fit the style and are a more suburban look than any urban style. IF and a big if this guy was from the west coast Chicano culture I would say he was more migrant worker.
In my opinion he was most likely just going for a nondescript suburban look.. Average Joe in the crowd. Too clean for grunge, no tan or rough hands from migrant work.
:Edit: The way he wore his plaid shirt could tell us more about his style and personality. Unbotton and opened? More casual, laid back guy.. Buttoned up and tucked in? More suburban, serious type of guy.
I agree. The shoes are kind of the deciding factor for me as to what the overall ensemble might indicate--in terms of a "sought-after-style"--as opposed to truly living the look-if that makes sense...
The low-rider look from East LA., and other places around the country (I lived in areas, both on the West and East coast where variations on this style were sported), is also all about the tennis shoes--and those were usually a big part of the overall ensemble.
But this doesn't mean that someone might not take bits and pieces of that style and weave it into their own look.
The Timberlands Lyle is wearing, when I could find similar ones on Ebay in their vintage sales, have a distinct grunge-look element, though. They were hipster-grunge, and the more worn the look, apparently the better.
And where was that look most popular in the '90s?
Seattle!
And Lyle died about an hour out of Seattle.
I keep wondering what leads might have been developed if the boots had been seen way back then.
Lyle could easily have aspired to be a part of the grunge scene, in some form or fashion. Maybe that's why he kept a pen in pocket--in case song lyrics popped into his head... Who knows?
But the fact that he coifed a bit, cared how his hair looked--that his appearance seems to have been important to him (so much so that he basically kept the look to the very end) might mean that his look was as deliberate, as most of his final actions appear to be. If that's the case, the look he was going for, could be telling.
We can't know what dreams might draw a person like Lyle to a given location--but the boots indicate that he may have been trying to fit into the grunge look that was popular in that region, at that time. He may not have been truly part of that scene, only influenced by it. And my memory of Grunge (though admittedly, it was not my scene) is that it wasn't heavily tattoo oriented. Herion-chic was more the sought after affect--so being super skinny, kind of went with the look. And of course, heroin was in fact a central part of that scene for many. So if Lyle didn't like doing drugs, maybe he found a way to attain the look, anyway.
I'm a contemporary of Lyle's and I remember the fashion of that time. It was fun and cheap. Nothing Lyle is wearing couldn't have been found on the cheap. It's not an expensive ensemble, except for the shoes.
I wasn't punk, but I liked the some aspects of the punk look, so I used them. I only recently got rid of my Doc Martens from that period. I have a friend who still has her purple Docs in storage.
The other reason to focus on those boots, though, is that from the internet searches I made, they appear to have been a one-off. I couldn't find any Timberlands with those soles. The top part of the boot yes--but even there, this boot is not what Timberland is known for. There might not have been all that many made, and they may only have sold in a specific region. They are unusual enough, that they might hold some tangible leads, in and unto themselves. And if Lyle was emulating a Seattle grunge/hipster look, that could be telling as well.
Just trying to narrow the regions he might be remembered from.
Those boots were well, well worn---he either bought them second hand, or he wore them a lot and may have owned them for almost a decade.