If you have a sneak skill at 100, will the Jester's Hat further improve the sneak skill?
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1Don't like? Don't wear it. Your loss :). – Mixxiphoid Sep 29 '15 at 17:29
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Realistically speaking, at 100 sneak, you're probably never going to be found. – Unionhawk Sep 29 '15 at 18:43
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@Unionhawk tell that the Ebony Warrior when you try to pickpocket him :(... – Mixxiphoid Sep 29 '15 at 19:16
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If an item will give you a boost in a certain skill, it will always increase that skill. The maximum reachable level for a skill through training/experience is level 100, but items like the Jester's hat will increase it beyond level 100.
You might or might not notice any difference since your sneak is already so high, but your sneak will be better none the less.
Mixxiphoid
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Do have any sources for this? Not that I don't believe you, but screenshots/wiki's? – Elias Benevedes Sep 29 '15 at 18:39
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1I finished Skyrim once and had a few skills well over 100 (including sneak ;)). Another good example is Smithing where it makes it possible to get an Iron Armor to Legendary. That would not be possible with just level 100. Also see this and this – Mixxiphoid Sep 29 '15 at 19:15