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Unless I'm chasing Engineer buildings or a specific player, I practically select the disguise at random to save time, avoiding slower classes. Is it possible to make informed disguising decisions at all times?
While disguises may not fool experienced players, they are mandatory to spoof Engineer's turrets.
Pros and Cons for disguising as each class.
PROS: Changes your hitbox, harder to headshot you.
CONS: Does not speed you up in any way, and you can't double jump. This shows the enemy immediately that it's not a Scout.
OVERALL: Would not recommend - the enemy expects you to shoot, double jump and sprint, none of which you can actually do while disguised.
PROS: You don't need to have a degree in method acting to do well in this, just walk along with the enemy team, scream "MEDIC" every once in a while, and don't run into your team, because they would expect you to shoot.
CONS: Makes you slower, and if you are disguising as an experienced player, the enemy might expect you to rocket jump and get suspicious if you don't.
OVERALL: Good for some players. Depends on your playstyle.
PROS: Easy as hell, and doesn't slow you down at all. You can just act natural, as if you are actually playing Pyro.
CONS: You can't backstab very well, as a Pyro is expected to be the frontmost person in the enemy line of defense, and if a Pyro is hanging back behind, the enemy will get suspicious
OVERALL: Good, but only for assassination - don't try chainstabbing with this.
PROS: Doesn't slow you, you can stick behind the team, don't need to do much to look realistic.
CONS: Experienced players will expect you to charge, or sticky jump. If you are disguised as someone who looks relatively new, they may pass, but it is risky.
OVERALL: Great, but once again, depends on your playstyle.
PROS: Nobody suspects you, ever, because nobody ever disguises as heavy.
CONS: Where do I begin. Movement speed, frontline, easy to headshot as the heavy's neck, a very easy target, is right where your head is.
OVERALL: Depends on your skill level. If you can handle the cons, then the pros outweigh them.
PROS: Amazing on Defense. A Spy disguised as Engineer would never be checked if he is near a sentry. Also, you can easily stay next to other engies, without any doubt. Then you can sap their crap and stab them.
CONS: Needs to look realistic - takes practice and a bit of method acting.
OVERALL: Good if the enemies are Defending, meh if they are attacking.
PROS: People with low health run to you like dogs to the hunt, and you can easily finish them off with an easy facestab or an Ambassador headshot.
CONS: If you don't heal people, they might check you, which is bad.
OVERALL: Once again, depends on skill.
PROS: If you're in a Sniper spot, your disguise has their primary weapon out, and you're crouching, nobody ever checks you, unless they're a W+m1. Method acting at its finest.
CONS: Hard to get to a sniper spot without being checked - an out-of-place sniper is very rare in TF2.
OVERALL: Good, but you may need a safe place to uncloak when getting to the Sniper spot.
PROS: Very efficient if you know how to use it; you can be behind the enemy team, not many people will spycheck you - and if you uncloak in front of the enemy, they won't be too scared.
CONS: Hard as hell to play off well.
OVERALL: Skill-dependent.
All 9 disguises can have use depending on a large variety of situations and playstyles
But you should never assume that your disguise is going to keep you safe. In fact, you should always prepare for the worst happening (being spy-checked) and have a Plan B ready to go.
Some of the basics for disguises can be answered with some simple questions:
After you get the feel for how the enemy plays and after playing Spy yourself for a while, you can get pretty good with your disguises.
A BIG part of disguising that a lot of newer spies tend to not know is the fact that you can disguise as TEAMMATES as well as enemies. This can be paired with the Dead Ringer to create more believable "fake deaths" as if it looks like the enemy killed a Soldier, they may not think that it was a Dead Ringer Spy. Another possible use of teammate disguises can be used to lurer enemies in for trickstabs once you learn how to do them.
All in all, disguises should be used carefully, as there is definitely more to it than just disguising as a certain class just because it feels right.
The answer provided by Amitai does also include some nice facts about each disguise, I would recommend reading those as well :)
I disagree with some of the points made in the other answers so I'm adding this one.
When you haven't yet gotten into the enemy's turf, be disguised as either a teammate or an enemy Spy so the enemy doesn't know your team has a Spy. The former is good for Dead Ringer use and baiting enemies around corners and such, while the latter is more likely to be ignored by enemies at a glance. You should probably try not to be disguised as a teammate who's nearby if their cosmetics are too loud.
Amongst the enemy, there are three groups of disguises.
The most important thing about disguise choice is that you remain unpredictable. This is not the same thing as "disguise randomly all the time" - a smart team could realize the enemy Spy never disguises as the same thing twice in a row. If you end up making the enemy think you only disguise as one thing, you can do something else and fool them for a while (though of course this disadvantages you for a bit to start with).
