I started riding and racing road bikes around the same time near my join date in college. As a collegiate athlete, I rode a lugged steel bike with DT shifters, since that was all I could afford. I graduated to STI shifters, an alu frame and 10sp, mostly on gifts from other racers in the community, and I've continued to pay that forward now that I have a career and my own earnings.
Since then (earning my own $$$) I've graduated to higher tier stuff, usually Force/Ultegra level. I've also graduated to elite racing categories, and have had some seasons with team-issued equipment. Clothing is consistently provided.
None of it - the clothing, or the bike equipment, has been really top-end stuff. Does what I have meet my needs? I think so. Would DA/Red or Assos/Rapha stuff exceed my needs? IDK, not really sure how to answer that. Would I perform any better with it? Doubt it. Would I enjoy it more? Probably.
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"Your beauty is an aeroplane;
so high, my heart cannot bear the strain." -A.C. Jobim, Triste