My clothing tastes day to day are fairly simple, but I have made some big purchases over the years.
$800.00 on a pimping leather jacked from my single days. Still wear it occasionally.
I spent about $1000.00 on 2 pairs of Black Jack Alligator Boots several years ago. Judging by their prices now, I should probably look at that as more of an investment than a purchase. Holy fuck are they expensive now.
I spent $1500.00 for a tuxedo and vast array of accoutrement (Ties, cumberbuns, vests etc)
I also spent about $1500.00 on a kilt package. I lived in Scotland at the time and got married in it.
If you go to a lot of formal events, the kilt and tux purchase will pay for itself since you will not need to rent. Those 2 purchases have definitely paid for themselves a few times over.