(Only listing things I bought myself)
In the 90s I bought a Gameboy clone from the Tandy.
My first own console I bought in 1996 or so:
Philips CDi Player, can't remember the model exactly but it could play video movie cd's as well, this was it: (I still have it somewhere in a box complete with a large game/movie collection)
Also I had an internet package with it including a dial-up modem and keyboard... Oh the phone bills.....
Not sure which year exactly but I've also bought a gameboy pocket around 1998 I believe it was.
My first own computer was a Casio Casiopeia E-100 (1999/2000):
I bought a compact flash modem for it so I could use internet with a Dial-Up connection.
Also played lots of hours of Solitair on it...
The first Palm-size PC model by Casio to have a color screen, the E-100 was outwardly identical to the E-15.
My first laptop (2003) (Windows XP 32bit):
Packardbell iGO with a 2.0Ghz Celeron and ATi express graphics, good enough to play GTA Vice City
Bought FarCry, returned the game, it didn't work because of lacking the correct shader version.
Oh and no built-in WiFi or webcam at the time, had my first "high-speed" broadband internet connection (2mbps ADSL IIRC)
My first Desktop PC (2006):
Acer Aspire E500 with 3.0GHz Pentium 4 630, ATi X300SE, Windows XP.
Then around 2007 or so I bought a Gigabyte P31(?) MATX motherboard with an intel E2200 CPU, installed it in this Acer case.
Had various GPU's:
Club3D ATi X1600 Pro
XFX Nvidia 6800 GS XXX
Sapphire ATi X1600 XT
PowerColor ATi X1950 Pro
Gigabyte ATi 3870
Gigabyte ATi 4870
HIS ATi 4870
Later on in 2007/2008 I built my own PC with some aluminium Lian Li case , ATX motherboard with an intel E7200. Windows XP 64 bit/Vista.
(My dad is still using this PC with E7200, Asus motherboard and the HIS ATi 4870.)
2009 I bought an blue Acer Aspire One D250 Laptop with some intel Atom CPU (Dual boot XP/7):
Spilled lemonade over the keyboard but I still have this laptop and it still works.
In 2010 I bought an Asus N53JQ Laptop with an i7 740QM 2.93GHz CPU + Nvidia GT425M
In 2014 I bought an Asus G750 ROG Laptop with an intel i7-4700HQ CPU + Nvidia GTX770M:
Then in 2016 I built a new PC with intel i5 6500 and GTX1070, later a CPU upgrade to i7 6700K and just recently a GPU upgrade to RTX 2070 Super which I'm using now. (in my system specs)
In 2017 I bought this 14" HP intel Laptop I still use. (in my system specs)
Edit: Added some more things and GPU list.