artlarprogue
I have no idea where to put this, but I had a player ask a really good question about rogues:
Why are they always depicted wearing so many belts?
I've been googling this for a few hours, and while I think there is a reason beyond the "Many Belts" TV trope, I can't find it. What is this about? Why are rogues/thieves so commonly depicted wearing so many belts?
This DM screen was released in August 2008, a couple of months after the first PHB, MM, and DMG were released (June 2008). MM2 and PHB2 weren't out until 2009 so this likely features exclusively MM1 monsters. It was illustrated by the late Francis Tsai, whose signature can be found in the lava in the bottom right.
Characters in the image are numbered from left to right. The indistinct background characters have been left out. Click to zoom in on the image.
Either a Gargoyle (MM p115) or a War Devil (MM p67, depicted p66)
(Not identified. Broad-built pale-skinned brooding dudes standing around holding hand-scythes aren't prominently illustrated anywhere in MM1 or DMG1.)
A Beholder, found on MM p32
A Lamia, found on MM p174, also depicted turning into beetles. Turning into a swarm is one of her abilities. (Identified by Jadasc)
A Mind Flayer, found on MM pp188–189
An Umber Hulk, found on MM p256
A Black Dragon, found on MM pp75–76, illustrated on p77
Looks like a Bugbear, MM p135, given it looks like it's fuzzy right down to its brow.
Looks like a very buff Goblin or Hobgoblin (MM pp136–141) or an Orc (pp203–205). Illustrations on all three of these varied a bunch between artists. If it's a hobgoblin they changed its colors, but they did that as well for the troglodytes next on this list.
Very likely Troglodytes, found on MM pp252–253. The anatomy's almost identical, but here they're depicted brown instead of blue. (identified by Adriano Varoli Piazza)
You could also consider Nerf guns. They won't require eye protection like paintball and airsoft guns do. Projectiles are cheap and guns seem to be in a similar or lower price range compared to a latex sword.
With some creativity and a splash of paint their bright colour schemes don't need to break immersion (although I would advise against "open-carrying" real-looking toy guns):
The only drawbacks are limited range (especially outside, in windy conditions) and the need to collect your projectiles after firing them (although you could try making your own biodegradable nerf darts).
Best Answer
They don't usually wear that many, but generally speaking, Rogues are the stereotypical "prepared for everything" character. They need belts because belts means pouches and other storage locations for stuff. And they have lots of stuff.
As a Rogue, you need room for lockpicks, skeleton keys, daggers, trap-disabling tools, smokebombs, caltrops, coins and gems, poisons, acids, mirrors, and who knows what other things you need when you're a dungeon-looting badass.
As a result, they have more belts and pouches and other storage kits than most people. Which then becomes a stereotype in itself, and so people start to exaggerate.