The first system you had that was "high end/audiophile", by you standards

I did have some others before, but the first system that hooked me on this passion/hobby and would still be pretty good today was:

Stacked Large Walnut Advents, with the top ones upside down so the tweeters were close together,
Yamaha CA-1000 integrated (usually run in the class A mode)
Yamaha top end direct drive turntable (YP-800?) with ADC XLM II cartridge 
Yamaha CT-7000 tuner
Early Monster interconnects and speaker cables 
Advent cassette deck
Teac reel to reel with 10" reels (model ?)

The first thing(s) that were replaced was the Large Advents that gave way to a pair of 
Dahlquist DQ-10.

From that system I have gone on to several others that I have enjoyed, but I do remember that first one.

1985+/-. ARC SP10II, Oracle Delphi, Micro Benz Glider, Threshold SA3, Thiels CA3 w/Mod. Sounded pretty good to me at the time, but in retrospect I wish I had my present set of Silverline Bolero's. I could really still enjoy this combo (ex Thiels) if I had it today, but one must move on mustn't one.
Problem I have with the OP question is what I considered to be “high end” has evolved over the years. When Walkman’s came out I thought that was high end - I was blown away by their sound. 
First High-End System (Early 90’s)

. KEF Reference 102’s w/KUBE
. NAD 7225 Stereo Receiver (later used as a Tuner/Preamplifier)
. B&K ST-140 Power Amplifier (came later on)
. Magnum-Dynalab FT-101 FM Tuner
. Pioneer Elite PD-65 CD Player
. Nakamichi BX-300 Cassette Deck
. Cables & Interconnects

Then became....

. Speakers remained as above, but driven with....
. Adcom GFA-545 MkII Power Amplifier
. Adcom GFP-750 Preamplifier (Active/Passive)

And Then Added....

. PS Audio GCPH Phono Preamplifier
. Thorens TD-160/Jelco SA-750D Tone Arm/Sumiko BPS-EVO

And Added....

. Technics SL-1210 M5G
. Nagaoka MP-200

And when I’m on the go....

. Audio-Technica MSR7B Headphones (next to be upgraded)
. Apple iPhone 12 PRO
. iFi xCAN or iFi Hip-DAC


When Walkman’s came out I thought that was high end - I was blown away by their sound.

ROTFLMAO believe it or not but one of the biggest boobs, er I mean respected, er I mean prolific posters on the site would have you believe his Walkman was the pinnacle of high end audio. Of course he also would have you believe he was a theoretical physicist and designer of interstellar propulsion systems..... you probably think I'm kidding. Ha!

The Gale's are one of the few things I sold that I regret.

Nice piece of engineering those speakers! the shape is weird, but amazing sound.