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Yeah i see what you mean i have thought this for a long time also. They looked a lot more awkward back then some of them. I think this is due to a few factors though like the Tech especially has improved drastically over the years from the wheel composition to the bearings etc i think this was a big factor because some of them you can really see had to push hard to gain speed. Go look at bladders 15 years later and they going much faster with less effort. Park layout is also a factor now that skate park design is more robust because these sports are more seasoned now. if you ever skated old TRS or old Majestic then the back cuff part of those skates where quite tall they went up way to far and this is part of the problem. Back then it was seen as good for support but overtime the designers and skaters realized that it was not good for movement because its to rigid. They are also very rigid and narrow boots this is all apart of the problem and is part of why they look funny when they skate. The plastic in the skates were also a lot stiffer too so that might also be part of it like look at jons run when he does his spins and at other key moments his lower leg and especially foot area look mega stiff when he goes on the ramps. If you look at 4:57 when he lands he does a nose Manuel with one of his skates this will be because of the back cuff area of the skate being so tall he cannot flex his leg properly when he lands like you can see in his body that he lands pretty naturally. Sure he lands in the edge of the hip but if that was a more modern boot we probably would not of saw that sort of result.

Like look also at how far apart the ramps are there is quite a lot of space in the layout here in this video and that means losing speed quicker.

some of it is also just mannerisms some people are more dorky looking compared to others. Idk many skaters looked dorky when they push back then though. Jonathan Bergeron in this video looks especially funny when he pushes. Idk there was a point like in the ealry 2000s when rollerbladders lost that dorky push and you rarely see it now its part mannerisms and part skate design. I think too the next generation after these kids just got better at looking more robust on skates.