English vs western for trail riding is totally subjective to the rider, but if the saddle doesn’t fit the rider (or is cheaply made) it doesn’t matter whether its an English or western saddle. It’ll be uncomfortable and the longer you’re in it the more you’ll notice. I, personally, am happy to trail ride in either type of saddle but I have my own saddles that I like and that fit me and my horses.
Any type of boot will probably be uncomfortable to go on a long ride in if they are new and not broken in yet- keep that in mind if you choose to wear a new pair of western boots. I would walk and ride and walk and ride to put a few hours of wear into them before heading out on a long trail ride.
Keep in mind, for a new rider especially, a 2+ hour ride will take some adjusting to (soreness wise!) but properly fitted tack and comfortable, broken in shoes helps!