Like most budding audiophile, I started with some budget gear and... (pretty much stayed there)!
When I first went off to college in '89, I used my roommates awful speakers. They were so bad, I wondered why I sprung the $$$ on a Dynaco 70 amplifier.
Then I bought a pair of RS4B Infinity tower speakers with the Emit tweeter. Not a good match with the tube gear. 35Ws of EL34 wasn't enough to control these 'solid state' speakers.
Pair of DIY Dynaudio monitors. Not very efficient, but a pretty good sound with the Dynaco Mark IVs I was running at the time.
1991 Apartment fire! Afterwards, through an audio dealer friend, I got a pair of Snell JIIIs. They never sounded good with my new H-K Citation V / Adcom 565 combo.
Homemade Jensen cabinets with 12" Stephens trusonic coax drivers. Sounded quite good with SE 2A3 or PP 6B4G amplifiers. Not WAF friendly, so they were sold to a friend. Last I heard, they were being used as PA speakers for a community theater!
Altec 755s in someone else's homemade cabinets. No treble, but a nice midrange.
(the dark years start). Onkyo bookshelf speakers as we need something out of the toddler's way.
Wharfedale W60s - nice midrange, no treble and a bloated bass.
Adire HE10.1 kit speakers. Efficient enough for SE 300B amps, but a little hard sounding.
Altec-Lansing Model 15 speakers. 32B horn with a 12" woofer. A little grainy sounding, but a step up in the sound department. I ended up parting them out as they were worth more that way!
UREI 813A studio monitors. Basically a time-aligned Altec 604-8K driver with an Eminence 15" 'helper' woofer on the bottom. The best I've ever heard for bass and dynamics. Forward sounding and not very kind for less-than-stellar sources.
and finally Magnepan 1.6/QRs. I lost the big dynamics, but gained imaging, smoothness and better soundstaging. I love the planar sound.