A lot of things in game cost shillings...a lot of shillings. the new sunset rider set cost well over 20,000 shillings. Not to mention that the JS limit is only 10,000.
The best way to make a lot of shillings is as follows:
Do a lot of side quests, not only do they give you shillings, but they give you items to sell, new races, and new areas sometimes!
Sell the unwanted quest rewards and other tack and clothes. quest items sell for quite a bit since you can only get them once. Because of this, be careful of what you sell.
Grind stable chores and races.
This way is kind of tedious but it makes pretty good money.