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Heat the oil in a medium skillet over medium.
Add the onions and cook, stirring occasionally, until caramelized, 30 to 35 minutes. You may need to add a tablespoon of water every 5 minutes or so when they look like they’re sticking.
Transfer the onions to a cutting board and roughly chop.
Meanwhile, cover the potatoes with water in a medium saucepan and season generously with salt.
Bring to a boil and cook until the potatoes are soft, about 12 minutes, then drain.
Transfer the potatoes back to the saucepan along with the sour cream, milk, butter, garlic powder, and onion powder.
Use a potato masher to mash the potatoes.
Stir in the caramelized onions and season with salt and pepper.
Transfer to a serving bowl and garnish with the chives and crispy shallots.