The 7 Creepiest Outfits In Flannery O’Connor

Like J.D. Salinger, Flannery O’Connor speaks the language of clothes. She nailed the art of extracting MAXIMUM value from a simple description of a coat or a hat or a dress. But while Salinger’s characters are generally rich New Yorkers who shop at department stores with assistants and rooms overflowing with furs, O’Connor’s are much different. It often seems that she has gone out of her way to dress her characters in a way that would make any reasonable person feel deeply unsettled.

Flannery O’Connor is a legend, and there are too many instances in which she gets clothing descriptions so, so right to name them all, so we’ll just go with the top seven (seven seems like O’Connor’s kind of number). Note: spoilers ahead!

7 Julian’s mother’s hat in “Everything That Rises Must Converge”

Yes, her hat. Everything that sucks about Julian’s mother—her racism, her forced cheer, her dumb and vaguely naive attitude—is somehow expressed by her hat: “It was a hideous hat. A purple velvet flap came down on one side of it and stood up on the other; the rest of it was green and looked like a cushion with the stuffing out. [Julian] decided it was less comical than jaunty and pathetic. Everything that gave her pleasure was small and depressed him.” This is a lot of weight for a hat to carry, but it’s clearly up to the task. Julian’s mother is a terrible person, and we know that before she even says anything significant. The hat told us.

6 Manley Pointer’s suit in “Good Country People”

Occupation: supposed Bible salesman. Suit: bright blue. Socks: yellow, and not pulled up far enough. Vibes: generally unnerving. In this story, Manley Pointer begins seducing a woman with a doctorate in philosophy who legally changed her name to Hulga at the age of twenty-one. One of Manley’s attempts at conversation is to ask Hulga if she has ever eaten a chicken that was two days old. Later, he opens his Bible to reveal a hollowed core housing his liquor, cards, and condoms. After he argues about which one of them believes in God less, he steals Hugla’s wooden leg. Read those sentences again, and then imagine him doing all of that while wearing a luminous blue suit and yellow socks. It’s powerful. And it freaks me out.

5 Powell’s sweatshirt in “A Circle in the Fire”

O’Connor clearly loved a good sweatshirt. She tends to throw them on her creepy sidekick characters, who are of course abundant in her stories. A classic example, worn by thirteen-year-old Powell: “He had on a sweat shirt with a faded destroyer on it but his chest was so hollow that the destroyer was broken in the middle and seemed on the point of going under.” What else do you need to know about this boy? Like Julian’s mother’s hat, the busted-up sweatshirt gives you an immediate sense of Powell’s character.

4 Bobby Lee’s sweat shirt in “A Good Man is Hard to Find”

The clothes in this story are everything, but let’s begin with Bobby Lee: “A fat boy in black trousers and a red sweat shirt with a silver stallion embossed on the front of it.” This story is so scary, so full of alarming details and description (see: “the line of woods gaped like a dark open mouth”), and the inexplicable red sweatshirt just makes everything worse. Where did he buy it? Why is he wearing it? Why red? Why a stallion? What does it mean? It means things are about to head swiftly south. I can’t pinpoint exactly why the t-shirt signifies this, but it does.

3 The General’s uniform in “A Late Encounter with the Enemy”

The hundred-and-four-year-old General wears a full-dress uniform to remind people of his participation in a war that he does not even remember anymore. History is no use to him. He believes he is a very handsome man, with his long, white hair and no teeth, sitting on the stage at his granddaughter’s graduation. He sits there in his uniform and knows that his attire means something, but of what, he’s unaware. He dies on that stage, and his uniformed corpse gets wheeled over to a Coca-Cola machine. The end.

2 Bailey’s shirt in “A Good Man is Hard to Find”

The shirt is yellow, with “bright blue parrots designed on it,” and is only described to the reader after Bailey crashes his car. First, we are told that Bailey’s face is as yellow as the shirt, and then, as he becomes more scared, we are told that his eyes are “as blue and intense as the parrots.” Leave it to Flannery O’Connor to make a kitschy parrot shirt become ominous. Bailey’s shirt is silly, and he is a goofy man, and you sort of want to laugh at the situation—until it all goes very, horribly wrong.

1 Everything The Misfit is wearing in “A Good Man is Hard to Find”

An escaped convict called The Misfit arrives in the story holding a black hat and a gun, wearing too-tight jeans, no shirt, and spectacles that give him “a scholarly look.” This paints a disturbing enough picture as it is, but after Bobby Lee and Hiram take Bailey out into the woods to shoot him, they come back with Bailey’s parrot shirt and the Misfit puts it on. The shirt, which had once been an indicator of Bailey’s basic silliness as a person, now becomes an emblem of something else altogether. The image of the shirt is suddenly chilling. Only Flannery O’Connor can pull that one off.