For me it was a 1992 Toyota Camry XLE. I was doing my six month stay in New Zealand wanted to have a new car when I came back for my six months in California. I knew exactly what I wanted and what I wanted to pay. I negotiated the price via email with a dealer in Los Angeles and picked the car up at the Sacramento Airport upon my arrival back to California.
My Current Car!! Well I didn't pay for it online, but I 'bought it'' online. Had to travel half way across the country to pay for it and collect it but it was worth it...
Respect! If my memory doesn't play me false, the most expensive item I bought and paid for online was less than $1,000 e.g. a notebook, lawn mower and furniture. Guess I'd think twice about more expensive products or items let alone buying a car.
@Lon Tanner I always liked the Camry but the price was a bit on the high side. So I had a Carina station wagon which was OK as well.
I guess the most expensive purchase would have been a computer, or large flat screen TV. Most high-dollar purchases I want to see and evaluate before buying.
I bought a silver ottoman from Amazon. Not gray, but a soft silver leather. I don't let myself or anyone actually use it, but it makes me smile everytime I look at it.
I've bought a flat-screen TV, but my nice convection oven may have been more expensive. I've placed larger orders with JC Whitney (and in 1973 dollars), but that was not OnLine.
Well, since this post I have purchased an adjustable bed and mattress online, so I have to revise my answer.
If you take into account inflation, it would be two ceiling fixtures, but I ordered them from the Sears catalog in 1986, not the internet. Made in Italy. (What was I thinking?) I still like them. On the internet? Probably the braid rugs I ordered last year.
I just bought vintage 1980s barely used condition Lawman high waist bareback riding jeans from a lady on Poshmark. They took 40 years off my look .... not!