A better question is do you have your basics down?
What part of This shit is outdated mind you don't you understand?
When it comes to horse riding boots, they're specifically made for horse riding, not wandering around given how their soles are, in regards to jackboots without the nails and heel they kinda wear away breddy quick. Its tile you gotta be careful with them, pavement isn't bad what so ever, DAK boots don't come with the nails, just the heels if I recall. A pair of concoran jumpboots might actually be up your alley if knee high boots seem a bit much for you. With the former two you'll have to find the shit reenactors recommend and use given my boots were custom made ten years back and still are good, the concorans they still make as they were back when.
You need a really sunny day to get some sort of use out of it. You're better off digging a hole and burning shit in it.
>~10lbs
>messenger/laptop bag
You fucked up. It fucked you up because you used it in an inappropriate manner. Shoulder bags are fine provided you actually use them for what they're designed for, mine don't bother me due to me not cramming in a million god damned things into them and if I so choose to do so they've all got belt loops/attach to belts no problem if that is the case.