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Sometimes it will feel like that cuz your shins aren't used to it from being all free over summer, but usually it's cuz they don't fit properly, try going to a boot fitter and buy proper fitted boots
They were fitted by a bootfitter and it shouldnt be from that because i litterally put them on and pushed forward which shouldnt be painfull i dont think
I get pains at the beginning of the season usually. Basically my feet freak out from being in a boot after not being in them for so long. Also, all the hair on my shins and calves gets rubbed off, which also sucks. I've been riding the same boot for 3 years now, so I know it's not a poor fitting boot cause after the first few times they're perfect, so yeah, it just takes a few times being in a boot for your feet to get used to them again.