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This JoytoKey profile is as close as I could get to matching the Xbox functionality, including hotkeys and menu functions. The left stick is programmed as both ASDW and the arrow keys, so it will navigate the inventory, however you will still have to use the right trigger to select the items.

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A simple .cfg file to use with JoytoKey which will mimic the Xbox functionality as near as possible due to the PC limitations.  You may need to File/Exit from Joytokey to refresh the list of profiles, since closing it by default just minimizes it.

To invert the right stick, simply use the in game Y inversion to invert the mouse.

The Grab function (left shoulder button) serves as the shift key to drop items in the inventory, as well as walking.  Left shoulder and the left stick will tab between menu sections (Inventory/spells/map).

Incidentally, you can quickly buy and sell with the left stick by pressing up/down to scroll to the item, press left to sell, then up to confirm or down to cancel.  Left also works as Take All, and right cancels out. This seems to be baked into the games arrow key functions, which I've dual mapped to the left stick with ASDW.

Edit 3/22/19: Small corrections made to the right sticks movement, mouse sensitivity in game is currently at 16-18.
Edit 3/27/19: Adjusted sensitivity of the right stick for archery/spellcasting, and Left Trigger now reduces look sensitivity by 70%.
Edit 4/12/19: Fine tuned the right stick, Auto run mapped to Long Press of Y button, Walk/Run Toggle mapped to Long Press of X button.

To avoid any conflicts with the game detecting the controller inputs, be sure to find the following line in your oblivion.ini and set it to 0:

bUse Joystick=0

Either download the file or use the following code: