The Informant: Desmond and Dempsey Makes Pajamas That Pass as Daywear


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Bedtime is for frayed underwear and poorly aged political T-shirts. Anything more is overkill; who, you might ask yourself, are you trying to impress?

But unfortunately, there are occasions when you’re trying to impress — family vacations, third dates, midnight interventions with judgy Ghosts of Christmas. Desmond and Dempsey’s Pocket Pajamas make comfortable, handsome options for any of those scenarios, with two bonuses: 1) they’re so comfortable that wearing them on a weeknight feels like a special treat, and 2) they’re so luxe that both the top and bottom pass for daywear in the summertime — which makes them well worth the $215 price tag when they’re competing with both itchy camp collar shirts from ASOS and that Bernie 2020 tee.

Desmond and Dempsey Pocket Pajama Set
Desmond and Dempsey Pocket Pajama Set

Desmond and Dempsey Pocket Pajama Set

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Price: $215.00

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$200 for something so underseen is not the type of investment I typically make, but the multifunctional aspect of D&D PJs is seductive. Furtively wearing pajama separates in the daytime has long been a summer hack for me, especially if the garments in question are a breathable 100% cotton, as the D&D set is. (The top actually passes as a piece from the same collections as my two most-worn camp-collar summer shirts: this one from The Kooples and a long-sleeved version of this one from AllSaints.)

And then there’s the fact that it’s just a lovely set to sleep in. After laundry day, the D&D set is the first thing I reach for, preferring to keep them well-loved rather than sitting in a drawer waiting for a special occasion. I’ve only washed this set twice since I’ve gotten it, but each time, it’s gotten softer and more comfortable without fading, pilling, or looking homely. I imagine even a year or two from now, I’ll still break them out when it’s time to star in a season of The White Lotus. 

I’ve also worn my set in two climates over the past two months: frigid December in New York, and humid 80-degree nights while traveling in Guyana. I felt snug in the Brooklyn chill and with the presence of a big fan, felt cool and comfortable in the heat of South America. Vacation pajamas indeed.

I’m also a big fan of the print, which feels tropical and sophisticated – the other styles are great too, including this lovely option in Jag Green. My favorite detail, though — and the most novel — is definitely the inclusion of pockets on the front of the shirt. It makes the PJs look more like a very light chore coat (e.g. this one I love from Alex MIll), reinforcing its covert function as a daywear piece. If you can hold an ID card or a phone in it, it’s safe for work. It doesn’t matter that at night, it’s holding your retainer.

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