--What are you wearing?
--My Burberry jacket, the one from the Christopher Bailey aviator collection.
--Why don’t you take that off?
--It has a rolled sheepskin collar and fantastic detailing at the cuffs.
--Do you want to know what I’m wearing?
--And under that I’ve got a cute little cardigan from Anna Sui, kind of a boucle knit.
--I’m wearing my boxers.
--I like to leave it unbuttoned, so you can see my cute little Stella McCartney top. It’s got a crew neck, with fantastic lace detailing.
--Don’t you want to know who designed my boxers?
--And then I couldn’t decide what to do for a skirt. The nubby Karl Lagerfeld? The wispy little Prada?
--Monsieur Jockey. Kind of appropriate, don’t you think?
--Thing is, your skirt kind of depends on your tights. It’s sort of an ensemble—you have to put everything together.
--Jockey, get it?
--There’s always Wolford--you can’t go wrong there. But I’ve been dying to try these fantastic Henry Holland tights. It’s like they’ve been spun out of cotton candy, they’re so sheer and delicate.
--You know--jock? As in jockstrap.
--And you can’t forget about shoes. Oh my God, I saw this girl yesterday, and she was wearing these things that looked like, I don’t know, Birkenstocks or something. It was like she was getting ready to hike in the Alps.
--Do you know why men have to wear jockstraps?
--So I thought maybe my Jimmys or, no, maybe the Manolos, and then I had this fantastic idea.
--Do you want to know what size mine is?
--I thought what if I just went with some little red sneakers? Keds, I just love the name.
--I meant the whatdoyoucallit?—the garment, not the you-know. But you can infer.
--They’re cute, and just a little bit ironic. Kind of a meta-comment on the whole fashion thing.
--Aren’t you getting kind of warm? Maybe you should take something off.
--I think you can take the whole shoe thing too far--you know what I mean? Though I do like that kind of high-heeled boot look.
--I’m driving in the car and all I’m wearing is the boxers--that’s how warm I am. I’ve got the AC going, but I’m thinking about you, and that just messes with my thermostat--you know what I’m saying?
--And I’m wearing my cute little Gautier bodice, the one with the lacy top.
--Oh God, I can’t keep my mind on the road! I’m swerving!
--But I don’t approve of that innerwear-as-outerwear statement. You know, the Thierry Mugler thing with those aggressively pointed bra cups?
--You know, I don’t mind that look so much. I kind of like it. But come on, what are you doing right now? What are you thinking about? You can tell me. Are you thinking something naughty?
--I’m thinking of going shopping. But I can’t decide. H & M or Loehman’s? What do you think?
--Let’s pretend you’re shopping. And I’m in the dressing room with you, and I’m still in my boxers and you need help unzipping. What do you do then?
--I ask you to hold my bags for me.
Charles McGrath, former Deputy Editor of The New Yorker and Editor of the New York Times Book Review, is Writer-at-Large for the Times.