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Curious what y'all think the best options are as far as hopping out and or hitching through California or whether it's worth it to just go around Cali and then from Oregon or Nevada to nor Cal

I'm doing some hitching and train hopping through the desert and beyond. I don't know if I should take my 14 eye black docs or these military type hiking boots I got at thrift store. My freind says my docs are unpractical but they're comfortable and everything I'm not sure I need advice. Do...