"So that car looks like absolute crap now. And tbh, it still probably wasn't the best even in the day, but nevertheless it probably still looked like a decent enough win."
That thing was a shitty little econobox even when it was brand new. I don't recognize the make/model, but it's along the same lines as a Subaru Justy, Ford Fiesta and Festiva, Geo Metro, Yugo GV, etc. No one ever thought cars like that looked good. People bought them because they were cheap and good on gas. It's a "decent enough win" because even the cheapest new cars in the '80s or '90s cost several thousand dollars. The cheapest one during my lifetime of nearly 50 years was the Yugo GV, which had a base MSRP of $3,990 in the mid 1980s. Most similar subcompacts were at least in the $6,000 - $7,000 range at the time.
In my opinion, there were hardly any cars designed in the 1980s or later that look good. The third-generation Pontiac Firebird (introduced in 1982; used as "KITT" on the Knight Rider TV show) is about as good as it got. Nearly every vehicle that's currently mass-produced is ugly as homemade shoes, and the few that look okay only look okay because they copied an old design (such as the 21st century Dodge Challenger), and they still don't look anywhere near as good as the original cars they copied.
"I don't know if this is just a technology thing but the same applies to when you see old stereo systems, gaming systems, etc. Looked great at the time but now can only ever look crappy and old."
Old stereo systems look awesome; specifically, 1970s Japanese ones (e.g., Pioneer, Onkyo, Sony, JVC). They had thick aluminum faceplates, solid aluminum knobs and levers, backlit analog VU meters. And the best looking video game console of all time is the original "heavy sixer" Atari VCS (AKA: 2600) from 1977 IMO.
In any case, the closest word to what you're looking for is probably "passé."
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