The wonderful thing about "those oblivious to their privilege" is that it falls into Dunning-Kruger territory (that should be in one of those books, Miss Hunter). A white, middle-aged man like some of the morons I work with are completely oblivious to any privilege they have because they can't fathom how they're lucky. They have it too good to realize how good they have it. These idiots I'm surrounded with can't understand why being a woman, getting laid at the snap of your fingers, having a shirt you can look down any time you'd like, and fucking their way to the top, could ever been seen as a disadvantage. They don't have privilege, they just wake up everyday like anyone else, put their coveralls on one limb at a time, and take their tools to work. They aren't handed an education or free housing or drinks at the bar, how are they privileged?! Well, they also got their good-paying union job from the connections their daddy had, went to school where they couldn't fail because their uncle ran the shop course, and so long as they could manage to not spill their whiskey in the cab of the truck on their way to work, they're golden.
They lack the awareness of how lucky they are because that's not something they've ever considered from someone else's perspective. The idea that they have also had bad days or dark times, in their mind, disqualifies them from being privileged. They don't think that calling the girl working at the bar cute, or telling her to smile more, could be offensive because it's nice to be called cute. They're just honest, nice guys who are being nice because they had a good day. It's her fault she can't take a compliment. The stuck up bitch.
Although, it could be me tiring of the phrase "yeah, well men have it bad too!" when I see women being passed over for opportunities they are more than qualified for because of some mans preconceived notion. Watching a female apprentice bust her ass only to be sent home in place of a guy who takes a fifteen minute smoke break every hour. Hearing the foreman say "well, at least she was good to look at".
Yes, the world is stacked against everyone, nobody will ever argue that. It's just stacked against certain people more.