Like all of this things listed were cheap and anti-fashion at the time.
Time, maybe for some things but chucking on a pair of docs and a jacket isn’t time consuming, a Mohawk could be but you don’t style them every day. &tc.
Back then and today workwear is where it's at. Not reflective vest type of workwear, this kind of stuff. Comfy, durable, cut that prioritises function but doesn't ignore style (maybe unsurprisingly companies like it when their employees have a bit of drip), and unless the company sold out to fashion you're not paying extra for the brand (unless it's Engelbert-Strauss which is construction site Gucci. I mean it's still solid and functional it's just not worth the premium). Also available without cargo pockets if you insist, look for companies catering more towards service jobs than the trades.
Pretty much only downside is the lack of colour options. Be careful when thinking about dying stuff many synthetics don't dye well or at all, even when the fabric is pure cotton the thread is definitely polyester. Or even silica.
I do feel kind of simillarly betrayed. Watch Dogs were my forst point of reference into what hacker subcultures look like, and it has shaped a large part of my life - next month i's going to be 5 years I've worked as a Red Teamer in a cybersec company. I'm also mostly a poser, and the aesthetics simply makes it way more fun - making art that's tied into what you do is great, assuming you dont take it too seriously, of course. Not that I do it, but the way Watch Dogs portraied it, it was fun.
Is it neccessary? Of course not. Is it a shame there aren't many hackerspaces with cool street art, and hacktivists making over the top manifests ajd cool streetart around our town? A little bit.
I feel like he's just lamenting that the youth that are making things happen could make a statement with some distinct fashion. Style has always been important for him so I guess it's somewhat complaint adjacent, but I get the feeling it's less like "damn kids today!" and more like "it'd be better if it were this way".
