My first helmet was a medium and when I got it it fit really well, but then as the padding compressed, the helmet became too bug and would move around on my head making it a bit scary to do a head check when changing lanes etc. I got a new helmet, an XS HJC one (also matt black funnily enough). It was slightly too tight when I first got it (the next size up was noticeably too big and I didn't want to make the same mistake as I made with my first helmet) but now it fits perfectly. I'm pretty sure your one will change to suit your head a bit more with use.
On the boot front, I think most bike boots are pretty solid, that's kinda the point so they protect you if you go for a slide.
Never in the field of human conflict has so much been owed to so few by so many cheese eating surrender monkeys.
(Winston Churchill on the French.)
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