So when I was younger and I played ffx-2 (probably around age 10) I did not put much thought into who would do the best with a certain Dress Sphere, but now that I am replaying the game on the HD remaster version I was hoping to get some tips as to what Dress Spheres are he best to train each of the girls in. Thanks a bunch!

Two dark knights and an alchemist is kind of op but awesome, in my opinion. As far as I know it doesn't matter who is who, though I prefer Yuna and Paine to be dark knights and Rikku the alchemist.
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Once you get to the point where you can use trigger happy and get 9999 every shot, if you are very twitchy, very OP, at least that is my recollection. I honestly can't remember if you had to move through every sphere on the card, or what the requirement for that was.
The Psychic Dressphere is also really powerful, in the keeping you alive front couple that with ribbon and you can essentially become immune to all damage.
Maybe not optimal for dealing with bosses but definitely OP.
Just starting? 1x Festivalist, 1x Black Mage, 1x White Mage (the early -aga spells and random chance of -aga/flare make it very easy).
Levelling? 3 Lady Luck.
Bosses? 2 DK + 1 Alchemist.
Via infinito? 3x Mascot.
Just got my plat today so I am done with both FF for now. Ask away.
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How do you Alchemist? I hear its good for healing, but I can't find it. I'm in chapter 3, did I miss it, or does it come later.
In the end, the best dresses are the unique MAcot dresses each girl gets if you get a Episode Complete in every chapter in every location up to Chapter 5. They have cheap, REALLY powerful abilities… but obviously you won't be using them until the end of the game. Up until then, I'd say it varies by situation, and that it's a lot more fun to mix and match dresses than to stick with one overpowered setup.
By the end of the game, I'm pretty much keeping them in one or two dresspheres.
Paine – Dark Knight (w/ Swordplay garment grid, can't remember name) Yuna – Alchemist Rikku – Trainer (with Black Magic garment grid)
my favorite setup is:
Yuna: Gunner, Gun Mage, Black Mage, Psychic, Lady Luck, Mascot
Rikku: Thief, White Mage, Alchemist, Songstress, Festivalist, Mascot
Paine: Warrior, Dark Knight, Berserker, Samurai, Trainer, Mascot
I like to have a Berserker, a Dark Knight, and an Alchemist in my party.
Berserkers may not be as strong as Dark Knights since they sacrifice a few strength points for speed. They can learn Evade & Counter and Magic Counter, which makes it safe for them to afflict Berserk on themselves and literally go wild. They still have a generous amount of strength, however.
Dark Knight may not be as fast as Berserker, but none of the dresspheres in the game are stronger than Dark Knight. Especially its special move Darkness. It's a command that converts its user's HP to the power of the move, ignoring Shell or Protect, since it's neither a magical move nor a physical one.
Alchemist is truly the superior healer in this game. The wait-time for Stash is crazy long, but it's entirely worth it – everything is free! There are no numbers (item amount or MP) that count down to heal your party. You've access to the most powerful curative items in the game, and no amount of MP to use for a Full-Cure type move can beat that.
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Don't forget that accessories and Garment Grids play important roles in aiding your party too. Putting your Alchemist in a grid that allows her access to her White Magic (the Garment Grid is called 'White Signet', by the way – won from a Sphere Break challenge against a dog), for example, could prove to be a success. Alchemist is the superior healer, but it still doesn't come with Shell, Protect, Regen, etc. There does exist a glitch as well, that if your Dark Knight is equipped with the Ragnarok accessory, no HP will be sacrificed for Darkness.