Is it possible to boost skills beyond 100 points?

Solution 1:

if I have 100 points in light armor and I'm wearing a ring which gives me +12 to light armor, would it result in my Light Armor skill being 112

Yes. Your modified Light Armor skill is 112.

• For armor skills, each point above 100 is another 0.4% increase to armor. (Mind the 567 armor rating cap).
• For weapon skills, each point above 100 is a percent increase to damage.
• For crafting, each point above 100 increases the outcome when skill is involved. (upgrading, enchanting, etc).

For the other skills, going above 100 may not produce the expected effect. Pickpocketing, in particular, may overflow and give lower chance of success than you'd have with 100 skill.

Solution 2:

I found out that once my pickpocketing was 100, any other items that gave me pickpocketing wouldn't affect the chance of success. However, you can boost your outcome by using % modifier stats such as 20% more bow damage, 50% increased chance to pickpocket gold, etc.

Solution 3:

You can get skills past 100, but the boosts only work for certain things. Smithing is one, but only when you're upgrading weapons or armor. Same goes for alchemy and enchanting. When you're creating or upgrading, respectively. Weapon skills increase the stats on weapons, for example; if you have a weapon with 100 damage, and you get a 20% bonus to that skill type, it'd have 120 damage. Hope this helps.