For example at places like Mens Warehouse you can score some good deals on suits. $500-$1k for a good name and a good suit.
There are some amazing clothing stores in Westport and Greenwich, one comes to mind in particular named Micheals. I know someone who used to shop at said store, you can spend $10k in one shot. Sport jackets, $1k, Zenga shirts $200+.
In such areas $100 jeans are "thrifty"
