Does it make sense for your race to charge a smaller fee for the entry and then require the purchase of an Add-On?
For example, you could have a race fee of $20 and then a T-Shirt fee of $15 and a Jacket Fee of $50 – with each registrant required to purchase either the T-Shirt or the Jacket.
This can be set up near the bottom of the Registration Add-Ons page as shown above.
Note: You must also check the box to enable asking each registrant per event as shown below. Note to set the Minimum quantity to 0, since a registrant will be forced to make a minimum of 1 of a group of items by the Requirement set above.