Dad brought back classic Sony walkman WM-2 from Japan. My first own purchase was an Aiwa top of the range portable cassette player in 1988 - had Dolby noise reduction, and only slightly larger than a cassette box (although the battery clipped badly on to the bottom)! Didn't think much about headphones quality then.
Then got into minidisc, bought a sexy metallic blue Sharp MD-702 with LED display on the remote (swimming fish graphic!) on Tottenham Court Road, probably 1997, which got us through India. Although digital, audio quality (in retrospect) was not great. Funny thing was, it took years before iPods really got going, why did Minidisc not get v popular? Featured in the Matrix after all... My son is now using after I sourced a new battery on eBay.
Sony Clie T625 palm device bought cheap due to damaged packaging. 320x320 screen, 65K
colours. Great jog dial on the side, scroll through and click. "Graffiti" system of
writing with stylus. Infrared port, for "beaming" to other palm devices. USB
syncing with computer. Memory stick expandable memory. 33Mhz CPU! (Motorola Dragonball).
16Mb memory! Pretty sleek though: 11.8x7.2x1.25cm.
My fastest Palms were the Tungsten T3, with the sliding action which revealed the 480x320 screen, and the T5 (400MHz). By that time they had bluetooth. Screen was bigger than a lot of mobile phone screens at the time, bigger even than the blackberry screen. Even managed to surf the web via Sony Ericsson T610 bluetooth phone! My second hand NX73V had wifi via a cartridge plus (rubbish) camera, besides clamshell keyboard. But a bit of a brick- still, hey, George Clooney had one in Solaris!
Remember seeing an ipod for the first time on a plane, maybe coming back from India? My first iPod, 3rd generation, 20gb, from my wife in 2003, black and white screen, buttons light red, touch sensitive scroll wheel. Still works, although stopped using when it kept glitching and I had an iPhone anyway. Must be on my 6th battery and second hard drive.
First computer, desk lamp style iMac G4, bought from PC World for £1500. 800MHz,
15" flat panel screen (1024x768). 512Mb RAM. WIfi, also had modem port, originally used
phone line "dial-up") before Broadband. Originally Superdrive (DVD burner), 60Gb hard
drive. I replaced the hard drive first, up to 250Gb. superdrive replaced after
it broke, pretty tricky. Never actually died, just wouldn't work with lots of websites -
but did photo/video/audio editing. Used firewire for external storage, USB 1 was super
slow.
My first memory stick was 16Mb, I remember it cost about £30.
Used to listen while cycling using a bluetooth Mavizen blueye - gorgeous, never got the voice control to work, but did the job before combined headsets came along and decent MP3 playing phones...
We both had black and white screen Sony Ericsson mobiles to begin with. Then Pauline had the lovely siemens sl55, one of the tiniest and certainly one of the most gorgeous phones ever. But poor quality, and Siemens gave up on mobile phones eventually (but still make cordless!). Left behind in NY airport. Nokia 5230 phone for a long time. Lovely screen, good music, camera pretty poor. No software.
Now on Late 2009 iMac, 21.5", 3.06GHz core 2 duo. 8GB RAM, 500Gb hard drive plus 3TB external Porsche design Lacie USB3 drive. Current i7 chips at least 3 times faster... Paid £605.
Work have just given me an iPhone SE.