How can I “fix” his mentality that a man should pay for everything?

So my boyfriend was raised to feel like men should pay for everything; dates, food, trips etc. I was raised to feel like you should never rely on anyone to do everything for you. Ex. Say we're on a trip, if you've payed for the transportation and where we'll stay, I'll cover food, gas, and any other attractions we do while there. I love spending money on friends and family and show most of my appreciation through shopping sprees, getaways and small gifts. In his eyes he'll feel bad about me spending money on him or will feel like that staff at restaurants/ other places will look at him funny. It's not entirely his fault, whenever his parents get word that I've paid for anything they ask why I did and why didn't he. I'll usually butt-in and say that I insisted, and most of the time the things we do are my idea so ofc I'd paid for them, I feel like it's rude to plan something and expect someone else to pay for it.
How can I explain to him no one really cares about these standards as much anymore? And that in a relationship it's okay for your partner to carry her own weight?
How can I “fix” his mentality that a man should pay for everything?
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