PC world covered their list of top 50 gadgets in the past. I'm don't buy too much into the listings, other than that it is true that the Walkman changed a lot of things in America, and hence it deserves it #1 spot.
What I noticed is that some of the designs on these gadgets are surprisingly modern. I'd see gadgets like these on the shelfs of some stores in order to set itself apart from the crowd without being too gaudy. So I'm looking at gadget designs pre-1990...so that enough time has passed for those designs to look retro if they weren't timeless.
1. Sony Walkman TPS-L2 (1979)
5. Sony CDP-101 (1982)
10. Regency TR-1 (1954)
26. Nintendo Game Boy (1989)
Surprisingly, the sony walkman also looked pretty modern, as well as the Regency radio. Some say that the Regency radio's design was copied by the modern iPod. Like the iPods, they also came in multi colors.
35. Motorola DynaTAC 8000X (1983)
This is an example of not long lasting design. This brick was a foot long and weighed two pounds. It was considered the first mobile phone, and cost $4000. Can you imagine pulling this thing out of your pocket and asking a girl for her number with it? I'm not sure whether it's not a long lasting design simply because of its sheer size in comparison to the gadgets now, making it unwieldy, or if it's just not pleasing to look at.