I think you miss the point. If you make the type of tips you say you do, there would be no problem going out and buying a 300$ pair of boots. There wouldn't even be a consideration to the price.
Me, I have a pair of Sorels for the deep winter with a rating of -100
I have a pair of bafins for lighter winter.
I have a some cheap pair of rubber boots for sloshing around in water and muddy trenches
I have been breaking in a pair of Helly Hansens that I wanted to try as I like their product.
I have a par of caterpillars I liked.
I have a pair of Dakotas with the Met guard for when at the mines.
I have a pair of steel toed sneakers for when I am in an office setting and not on a construction site
I have a pair of Harley Davidson flat toed riding boots
Then my old ones.
Do you want to know what pants I wear as well?
Maybe what underwear I find most comfortable or will you just leave Vert to those type of questions?
"If you make the type of tips you say you do..."
What are you talking about? I don't make a crazy amount of money, bro. Apparently bartenders make more than you thought and for whatever reason, this is driving you crazy, but 300 bucks is still 300 bucks.
And let me point out something else about your idiot math. Did you notice how you rolled out this long list of boots in some weak attempt to be impressive? Yeah, this is in the middle ages. Everybody has several pairs. I have sneakers to run in, sneakers to wear shorts in, boots to wear casually, boots to go carpenter **** in, boots for bartending. You act like i'm going to spend $300 one and only one time and buy a single pair of boots and wear them every single day for three years. You're an idiot.