For me, I think it's my Cheaney FS029 boots. I paid about $290 + $100 VAT, and I wear these 3 seasons a year. I wear them at the office and on weekends. I have gotten more than my money's worth, and they are still going strong. This was a great purchase.
The other was my Banana Republic cardigan. I paid $100 and have worn it regularly for 5 years. It is still going strong. This was a great purchase.
What about you?