Got my L's and new Ninja250r last week

I think I've made my mind up on gettin some Draggin or similar. (If you disagree please comment)
Not sure with footwear, My rides so far have been around to friends places and up a couple roads like Mount Keira Rd and I have just been wearing my comfort shoes - Globe skate shoes (have laces), I intend on riding some more of the nice roads down south here with mates and Phil and the guys from here when they go to the natio etc. I will also more than probably ride to work

I guess ultimately what I'm asking is;
1. Are my work boots fine/safe?
2. Are my Globes okay for going round to my mates? short rides up the mountain roads?(keeping in mind ATM I am taking it easy due to learning)
3. I've just been on holidays and so have little money right now, do I really have to buy a pair of riding boots right now?
Thanks Guys