Jeniene Ferguson looks like she’s about a 36B, give or take a cup size. I’m not the first person to try and guess. Her male customers, shopping for their wives, often attempt the same mental arithmetic. “I ask, ‘What size do you think she is?’ ‘Oh, she’s your size,’” Jeniene mimicked, putting on a deadbeat-sitcom-husband voice as she acts out the scene. “‘My size? Okay.’” That “okay” — which Jeniene uttered with her eyebrows furrowed, her hands raised in defense against the assault of male cluelessness, the emphasis flat across the two syllables — dripped with sarcasm. “And the bra comes back, because turns out she’s a 34A or a 42D.” She rolled her eyes. She knew it would. Jeniene is the owner of Lady Olga’s Lingerie in Hamden, Connecticut, and there’s very little she doesn’t know about bras. She’s been in the business since 1987, when she and her mother (the eponymous Olga) opened the store together. It’s a small space, nestled in a tiny strip mall. The walls are bedecked with lace and satin and capital-D Decor, like the sculptural white deer head at the entrance. When I visited around Halloween, he was wearing a festive pink half mask, which matched the pink jack-o’-lantern on...