In Oblivion Remastered, you can get lockpicks mainly through the following methods:

• Buying from Shady Sam : He is the most accessible vendor for lockpicks, located outside the Imperial City walls near the Elven Gardens district. He sells up to 30 lockpicks daily at about 6 gold each, and his stock refreshes every day

• Joining the Thieves Guild : Once you join, you can buy lockpicks from fences who have a larger stock (up to 100 lockpicks). The first fence you encounter is Ongar the World-Weary in Bruma. This option requires progressing through the Thieves Guild questline

• Looting : Lockpicks can often be found as loot on bandits, goblins, and in chests or barrels in dungeons and caves. This method is free but less reliable than buying

• Quest Reward : Completing the Nocturnal Daedric Shrine quest grants the Skeleton Key, an unbreakable lockpick that greatly aids in lockpicking

For quick restocking, Shady Sam is the easiest and most consistent source early in the game. Later, joining the Thieves Guild opens up more plentiful options. Meanwhile, looting remains a supplementary way to gather lockpicks during exploration