Originally Posted by
Segev
Hm. How about:
If you fail a Strength check for any reason while wearing Gauntlets of Ogre Strength, you may re-roll it, treating your Strength score as 19. You must take the new result. Your Strength is treated as no less than 19 for any static calculations.
Or reword that last bit for better "fit" with 5e vernacular; the idea being that 19 is a "floor" on your strength for static value purposes. (This would include any stat damage failing to bring you below 19. ...actually, is stat damage even still a thing in 5e?)