If your Pokemon could hold two items...

[Twilight-kun]

Which would you choose?

Can't be the same type of item, for example, can't have a Splash Plate and Mystic water on a water pokemon

I'd say give Pikachu a Light Ball and Eviolite

or give a Super Luck Unfezent a Scope Lens and Sharp Beak

 

[Sydian]

That'd be pretty game breaking...lol.

 

[Twilight-kun]

Ah, but it would make tournaments so much more fun and complex

as if a level 5 Tailow with a Focus Sash, Endeaver and Quick Attack wasn't?

 

[-Grayscale-]

Life Orb and Leftovers... or just 2 Life Orbs

OP

 

[Ephemeral Euphoria]

I'd use a Choice Specs and Choice Scarf on my Kyogre. Enjoy your rape.

 

[Gulpin]

For me it would really depend on the situation. If I were EV training I would probably equip both a Macho Brace and a Power Item so I could yield up to 28 EV's per defeat. However, if I were battling I would do something similar to the two posters above me. During regular gameplay I probably wouldn't attach any at all, as I rarely attach one item as it is now.

 

[PlatinumDude]

Pretty game-breaking, like Sydian said.

Anyway, Leftovers + Life Orb for me, since Leftovers will slightly restore the HP that LO drains away.

And if I'm EV training, 2 Power items would be best.

 

[WasSollDas]

That would be quite interesting, but it could also turn out to be extremely confusing.

For example, let's say Heatran has TWO balloons. The other trainer sees that Heatran has a balloon and pops the first one. Then it trys to use earthquake when he realizes that the Heatran has ANOTHER balloon. If the trainer was me, I would really go nuts.

I think I would go for:
-double balloon
-double rest-chesto
-life orb + leftovers (this is probably going to be the most popular one)

Also, how would trick work if a pokemon has two items?

 

[Twilight-kun]

You wouldn't be able to equip two items that do the same thing, like 2 Life Orbs or two items that boost a stat, like two Choice items

the LO and Leftovers seems like a good combo though

 

[Satoshi Ookami]

That would be pretty awesome :D I actually though of it yesterday!
It would also help in in-game training... you could equip Lucky Egg and some boosting item =)
I would love to have Lucky Egg + Metronome on my Lucario xD
And Life Orb + Leftrovers simply rocks =D

 

[Mr Cat Dog]

When training Pokemon, having a Lucky Egg in addition to any other item that might be used on a critter - like an anti-Poison berry if you're fighting a lot of Poison critters or something similar. The Lucky Egg is probably my favourite item, and just combining it with something else can only result in good times.

 

[Twilight-kun]

Lucky Egg and Amulet Coin

More exp and money!

 

[Mystical Mermaid]

I'm sure there'd be some potential game-breaking item combinations if this was done. One way to balance it out might be for each Pokemon to have an "Accessory" slot and a "Berry" slot so that you're limited to one of each kind of item.

 

[Zephele]

Lucky Egg and Exp. Share might work for a ton of easy experience when levelling up someone particularly weak.
I was also thinking maybe a Choice item and Metronome could work in tandem with each other?

 

[Plasmette]

Soul Dew and Choice Specs on a Latios or Latias. Latrollolololol

 

[Twilight-kun]

I like the item+Berry combo idea

Focus Sash+Sitrus Berry?

 

[XtinaIsMeLuvinWWE]

Exp. Share and Shell Bell or Amulet Coin and Charcoal, something like that lol :)

 

[Katie the Friendly Ghost]

No one has said Lucky Egg + Lucky Egg yet? For battling purposes I'd probably use the item that raises critical hit ratio (scope lens?) and probably just the stab-raising item or whatever those hold items are called haha. As you can tell I'm not very much into competitive battling.

 

[ShinyUmbreon189]

You always gotta have leftovers and the other one would be an item that increases that certain pokemons move types.

 

[Legobricks]

I came up with this Eviolite-holding Scyther build based around using Fury Cutter and Reversal. With the addition of a Wide Lens, the former move's 5% chance to miss wouldn't randomly screw the whole thing over.

Can't be the same type of item, for example, can't have a Splash Plate and Mystic water on a water pokemon

Why not? The effects should stack.