Hi Bayleigh,
Haha I stress over first day of school outfits as well, but mostly because I want to make a good impression on all my new teachers.
I think the boots would be a great idea! I just got a pair of doctor martens as well
Just make sure that you're comfortable though, because the doc martens can be a bit painful when you're still breaking them in.
Feel free to message me if you would like to talk!
Kyra