Downplayed: Bob has the cheapest equipment available from the starting area's shop.
[Bob's Clothes] were made on the cheap by his mother. Hence there are no clothes like them, but they are neither valuable nor designed for combat. While there are obviously other [Stick] lying around he sees no reason to pick them up when he finds an actual weapon.
Bob is decked out in full, modern combat gear — but since he's fighting aliens, it's dramatically inferior to their equipment anyway.
Bob's a random peasant, so it wouldn't make sense to have him start with the Infinity+1 Sword.
More advanced weaponry requires greater skill to use, so it makes sense that an inexperienced character would start with something basic.
Inverted: Bob begins with the most powerful equipment in the game, which can be bought anywhere. However it breaks rather quickly when it's used.
Subverted: Alice immediately goes into the armoury and trades in her equipment for some actual weapons and armour and gets some for Bob while she's at it.
Due to budget cuts, they can still only requisition equipment far inferior to what they'll find later.
Armor and weapons are next to worthless, since Bob still needs to level grind his magic/kung fu/etc.