I don't have black oxfords, but I'll try something similar with my Aldo brogues, maybe grey socks.
Probably part of the appeal for me is that it is the antithesis of what I saw at the fashion thing earlier this month where most of the women were wearing skinny jeans and heels. Not all fashion needs to be flattering. But everyone has their limits.
Anyways, honestly I think the hipster look is dead/mainstreamed, especially in Seattle. I realized this when I was in Ballard, a former blue collar with a streak of rock-a-billy neighborhood. Now overtaken by fancy condos and apartments. I stopped by a newish bar for a drink while running errands. The young woman next to me, wearing a plaid shirt, skinny jeans and New Balance sneakers; on her wrist, a Cartier Love bracelet and Cartier watch. Her wrist was worth more than my car, new.