Preppy Sleepwear And Defining “Naked” For A Tribe That Believes In Layers


This morning I woke up well rested but surprised at what I was wearing: a Brooks Brothers dress shirt and Churchill-dot boxer shorts. Seems I conked out in the middle of “Pompeii” for the third night in a row, which probably means it’s time to return the movie to Netflix.

As for what trad types wear when they’re actually preparing for sleep, Lisa Birnbach broaches the subject in the October issue of Town & Country with a piece entitled “The Lost Chapter Of The Preppy Handbook.” Already online, the piece has the dry humor that proliferates the OPH but is far scarcer in the more conceptual sequel.

For example:

Question: Are you allowed to sleep naked? First, let’s define naked. We are a tribe that believes in layers. You may be a little warm, but never so warm you wouldn’t want a sweater nearby. We like to be prepared. We also like hyperbole: “I feel naked without my pearls” or “I can’t relax without a blazer.”

Head over here for the full piece. And in the meantime, without creeping us all out, what do you wear to dreamland? Here are a few examples from Brooks Brothers catalogs from the time of the preppy handbook. And yes, BB still makes the nightshirt.




Oh, and here’s my idea for a sleepwear design: go-to-hell pajama set embroidered with little prescription symbols. — CC


Top image via Slow Love Life.

40 Comments on "Preppy Sleepwear And Defining “Naked” For A Tribe That Believes In Layers"

  1. Charlottesville | September 27, 2016 at 11:57 am |

    Funny article, Christian. Thanks for the link. I had forgotten about the lightweight cotton flannel Lanz nightgowns my wife used to wear in wintertime. I still use a piece cut from a discarded one as a shoe cloth. Brooks classic pajamas of the type pictured above for me, or sometimes a T-shirt in lieu of the top or boxers instead of the bottoms. Often topped with a seersucker robe from BB or a Navy chamois-cloth robe from LLB when toddling downstairs for coffee. I’m curious as to whether anyone under, say, 45 wears regulation pajamas these days. I assume it’s more for the middle and older set.

  2. My wife and I love our matching LLB flannel nightshirts in blackwatch plaid on cold nights, but I am sub-35 and those few houseguests who have seen it have teased me for it.

  3. Charlottesville — I have a set of vintage Brooks oxford cloth pajamas I found NOS that I wear when I am a guest or when hosting a guest. I often pair with a Brooks wool robe I bought on clearance during an after-Christmas sale.

    However, when it is just my wife and I, then I skip the formality and wear a t-shirt. I am 33.

  4. For a long time it’s just been fresh boxer-briefs and a t-shirt. I’ll throw on some pajama pants and sometimes a light flannel robe before leaving the bedroom to let the dogs out and pour some coffee.

    I seem to roll about and change position over the night, and find loose, full cut sleep garments tend to twist, bind and ride up uncomfortably. Depending on the material, they can also ‘catch’ on the bedding, which further contributes to the aforementioned issues.

    And thus, comfort takes precedence over tradition and style. The downside: it can be harder to get out from under the covers on a particularly chilly morning before the furnace has kicked in. To answer Charlottesville, I’m 31.

  5. Charlottesville | September 27, 2016 at 12:36 pm |

    Good to know that PJs are still around even for younger guys, at least on occasions when one might be spotted by hosts or guests. I would be remiss as a Virginian if I did not note that the old BB oxford pajamas (with top button) were better than the current model. How many Virginians does it take to change a light bulb? Three: one to change it and two to complain about how much better the old one was.

  6. Go-to-Hell Pajamas: The Cure for the Common Sleepwear.

  7. Charlottesville, I’m 18 and during the colder months I wear a white undershirt with flannel tartan pajamas pants and a flannel black-watch robe. However, I do have a nicer pajama set (Polo blue oxford cloth shirt and pants and vintage Polo oxford cloth robe) that I wear on certain occasions (i.e. Christmas morning and in front of guests) or whenever I feel like dressing up in the house.

  8. Question: how many people still wear opera/bedroom slippers of any kind? Either like the ones shown or a moccasin type. I have sheep’s fur lined moc slippers.

  9. Charlottesville | September 27, 2016 at 2:34 pm |

    GS — I wear the moccasin style of slippers most of the time, but own the other type as well. The main difference I am seeing in responses is that younger guys may see pajamas as something to wear in front of guests, whereas even on a warm night when I may sleep in boxers and a T-shirt, I don the PJs even if just for coffee with my wife. I think I went without real pajamas from the time I moved out of my parents’ house until about the time I got married, so maybe that is a common pattern. I tend to shower and dress before breakfast when I am either a host or a houseguest, whereas my wife is comfortable greeting family and friends in a robe, so maybe I just have a strange tendency to early morning formality.

  10. I’ve been wearing BB’s broadcloth nightshirts for years. Don’t know why they make them in non-iron, though. It’s never really been a problem.

  11. Working in higher ed has afforded me the opportunity to collect a number of pairs of basketball shorts–the official ones worn by the team on the court. Those, plus a short/long sleeved college or concert t-shirt (depending upon the season) are all I need. I do keep a pair of tartan flannel PJ pants from LLB by the bed for mornings during the colder months.

  12. Charlottesville, yes I call those my formal set of pajamas because I have tried sleeping in them but I felt like each time I turned (I move a lot before falling asleep) the collar wasn’t moving with me and it was uncomfortable. Therefor, I reserve those pajamas for certain occasions or whenever I feel like being “fancy”. In bed, it’s almost always boxer shorts and an undershirt. When it’s hot, no undershirt in bed, but around the house its either a robe, pants or both and always a shirt of some kind. As for slippers, I see the opera slippers as more of an older gentleman’s choice an do hope to wear them someday. Brooks has ones made in England but there’s still L.B. Evans (the original) making them overseas.

  13. Charlottesville | September 27, 2016 at 3:41 pm |

    Good for you, GS. Even at my relatively advanced age, the opera-style slippers feel a bit formal. I have a pair from Evans in black (the type my Father used to wear), but they spend most of their time on the shelf. I do wear velvet slippers with black tie at home, but these days that is usually confined to New Year’s Eve dinner à deux with my wife. A couple mentions have been made of nightshirts. I like the idea and have tried them repeatedly, but I always seem to end up by morning with the thing practically wrapped around my neck. I may give it another try though. Brooks and LL Bean both make good ones (or used to the last time I checked).

  14. Thank you, and my grandfather wore them, not my father, but I will wear them when I am older. Velvet smoking slippers too, and Belgian loafers. I feel as though they are in the same category of light house slipper. Also, I had the same problem of the shirt’s collar wrapping around my neck as I twisted and turned in the night, which is why I sleep shirtless most nights.

  15. You say pajamas, I say pyjamas, and I say the cat’s ones too, which by coincidence I seem to remember doing so here recently. So what can one say about this timeless nighttime attire? Very simply that I am a fan. One cannot beat a pair of the old jimjams – as I’m wont to call them – especially when it gets a bit taters outside. On the question of cold nights, I’m disappointed no one has confessed to wearing a nightcap…as opposed to drinking one, of course.

  16. Boxer briefs and a T-shirt in the warmer months, light silk longjohns in the colder ones. I, too, don’t like the looser fit of PJs, which catch and bind. Add a light shorty robe and my fleece lined slippers, and I’m good through a wide temp range.

  17. Charlottesville | September 27, 2016 at 4:57 pm |

    Bags – I have a nightcap, which was a gift. I have worn it once (for a photograph). I also have a fez and hope to wear it one day, sitting in a wing chair in front of the hearth with a silk dressing gown and velvet slippers for the full late Victorian look, but in addition to needing to obtain a silk D.G., I think I will need to drink several nightcaps before I get up the nerve for that one. Some things are better in the imagination than in reality.

  18. Just as I’ve never seen a straight banana, I’ve never met anyone who owns a night cap. Of course Wee Willy Winky wore a nightcap in addition to his nightgown, but it wouldn’t fit it into the nursery rhyme, to the despair of nightcap manufacturers everywhere.

  19. On all but the hottest nights I wear BB striped pajamas which button all the way up with a loop at the top or a pair of BB seersucker short pajamas which button up to a V neck. The wife wears one of my favorite white oxford cloth button downs from Troy Shirtmakers, and two drops of Chanel No. 5.


  20. I love a pair of standard pajamas, with a coat-style button top and full length bottoms with a drawstring waist. They make me feel relaxed and comfortable when I am ready for bed. I have worn Brooks Brothers (oxford cloth, broad cloth, or flannel), J. Press, and L.L. Bean (flannel) pajamas over the years. For warm weather, the top can have short sleeves and be a v-neck pullover style, and the bottoms can come down only to the knee.

    I remember shopping at Brooks with my grandmother in the 1980s and how she used to make sure the pajamas she chose for my grandfather had a drawstring waist; he refused to wear elastic. I also remember the language my other grandmother would use when she stayed with us, which sounded old-fashioned to me: “Now children, it’s getting close to time for bed. Go wash your teeth and put your sleepers on,” she would say.

    I had an L.L. Bean nightshirt in the late 80s and early 90s that I loved but by morning I always seemed to find the whole thing bunched up right to the top of my chest under my arms. I finally gave up on it.

  21. Boxers and a T, unless house guest or visiting elsewhere. For those occasions blue oxford cloth PJs so old they feel like broadcloth. Have a very heavy POLO shawl collar regimental striped long terrycloth robe from the early 80s prior to one size fits all era. Slippers, old Cole Haan shearling lined mocs, very old Topsiders and for when it’s very cold some very hideous Acorn slipper socks.

  22. Zippo

  23. Aha! Look at item C on the top left Brooks catalogue page, the cotton Madras coat style pajamas in wine! I still have and wear a pair of those!

  24. I wear masculine styled pajamas, cotton sateen in summer and flannel in winter as I try to live my life as if I found myself in a 1930s madcap romcom

  25. Mac, are your Cole Haan slippers so old that they’re US-made? If so, it’s a testament to how American manufacturing means quality and value.

  26. GS
    While I’ve always tried to buy American, I’m guilty of owning a pair of Nike Cole Haan “pinch” penny loafers made in India. They are my rainy day, ice on the walk shoes. It’s like owning a beater car so you can leave the BMW in the garage during ice storms. 😉

  27. Online incarnations of Ivy, Trad, and such occasionally inspire delusional thinking– that, back in the day (the 1980s), every decent, college-educated fellow had an eye for the sort of stuff here featured in the old Brooks catalogs. But we know better. Just as Julian Dedman’s droll editorial for a certain rag shed light on how Ivy was once (very much) a minority report among American gents, so is this saying sure and worthy of remembrance: At the time of its printing, this older Brooks catalog was being received (at home, by way of a mailbox) by maybe–maybe?–five percent or less of the American population. Okay, probably closer to two percent. Of this petite percentage, how many were, by 1985, still engaging in Anglophilia-driven habits like regimental striped pajamas? Maybe one percent? Save the uber brief Heyday (’62-’68?), Ivy/Trad-tending tastes weren’t alive-and-well among the masses. And it’s equally likely that it was repeatedly resurrected by fogeys of all ages and types. This is what modern-day attempts at The Look miss so frequently: it was always a look that appealed to the pipe-chomping, tweedy, Episcopalian grandfather inside each of us. Okay, inside most of us.

    …which is why, odd as it may seem, night caps may still be worn. As a matter of (by God, dammit!) principle.

    Sartorial anachronisms are, at heart, romantic in character. Tragically so–Always looking back with a sigh. Even the gents who wear this stuff because Miles, Bill Evans, and other jazz musicians once did–even they’re required to admit as much. They’re as old-fashioned as any fogey.

    I wonder if Bill Evans ever wore a nightcap.

  28. One problem with pajama bottoms of any kind is that for those of us with an inseam in the area of 30″, they’re almost always too long. Yes, I know I can have them hemmed, but it’s awful irritating.

  29. M Arthur

    I have a Zippo too, but I don’t smoke in bed. 😉

  30. Charlottesville | September 28, 2016 at 10:13 am |

    Good observations, SE. I can certainly corroborate that the 80s brought no sweeping Ivy renaissance among the masses, despite the temporary “preppy” phenomenon that made pink and Kelly green sweaters and wide wale corduroy shorts and skirts mainstream among college girls for a few years (which was a good thing in my opinion; see Christian’s tribute to girls, bikes and penny loafers from a while back). At my law school there was a fairly solid Ivy-style contingent (mostly from New England and the southeast), but in Washington I can think of only 2 of my new-lawyer contemporaries who had any awareness of the difference between a 3/2 sack and an Armani drape, or who could tell a Brooks OCBD from the ones at Britches of Georgetown. Most bought their suits at Sax or Burberry’s or wherever as soon as they had a few dollars in their pockets. Not necessarily poorly dressed compared to the average guy, but not Trad. I found much the same was true in NY in the late 80s and 90s. From my limited observations, maybe 2 to 5% knew the score, so to speak, mostly lawyers, very few in banking even though that was where the money was. Of course, all tradition is a form of looking back; learning from, revering or paying tribute to the past. Thankfully, there remains a (tiny) group of us who enjoy looking back. We are certainly not better than anyone else in any way that really matters, but we are different. And we recognize each other when we meet, even if we don’t say anything. As your inner Episcopalian grandfather might say, it is meet and right so to do.

  31. Mac, I also have a pair of made in India Cole Haan loafers as a spare pair. But are your CH slippers US-made?

  32. Sacre bleu! Come on SE, we’ll never be “as old-fashioned as any fogey”. We’ve still got the jazz, man. I even go and listen to jazz musicians who are still alive. Don’t be shocked. Chick Corea for example. So we’re still cool.
    It was always about the natural shouldered look jazz musicians carried off so well in those days. Most of the other stuff I could take or leave. I was an Ivy aberrant, with Italy and France vying for my attention.
    I think it was Miles who may have favoured nightcaps more than Bill, but I could be wrong. The old memory’s not what it…now what was I saying? Oh yeah, it was such a long, long time ago, when Ivy ruled the waves…long before GS’s dad was born.

  33. GS
    American made bought around 1980. I believe at that time most Ivy Style Cole Haans were made in Main or Chicago. You’d be surprised how many old American shoe companies were operating out of the Chicago area. The famous Horween Leather Co. is out of Chicago. If my memory is correct Cole Haan also came out with their Italian made shoes around 1980.

  34. @Bags, right you are.

  35. When I read the term “fogey” on this blog it reminds me of a frat pledge in Fall 1973 who told me I dressed like an old man. Kid had some balls. he was wearing bell bottoms jeans, Adidas running shoes and a black sweater with a large rose knitted on the center of his chest. Not long after, I asked him if he wanted to go on a road trip to Manhattan, Kansas with me and another member. We took him to Woody’s across the street from the KSU campus in Aggieville. Woody’s was an Ivy/Trad shop operating mostly university towns, from Ames to St Louis. Long story short, by Spring finals we had turned that kid into a full blown Ivy clothes horse. Even hippies can change.

  36. Mac, yes they moved to Maine sometime in the 70’s but I wonder why they had a line of Italian made shoes. Also, Florsheim was originally made in Chicago.

  37. Also, Mac, your story of converting that lost young man is amazing.

  38. I wear the BB blue and white stripe PJs but the drawstring waist can be troublesome if you toss and turn. I also have the BB Oxford robe but the Polo version of both have heavier material.

    The blue Peale & Co. slippers are great to wear; even on long flights instead of shoes.

  39. Evan Everhart | March 8, 2018 at 2:30 pm |

    I wear a pair of dark mustard colored broadcloth pajamas piped in burgundy, that my father gave me when I turned 17, or sometimes some blue oxford cloth ones, but mostly I wear these when I have guests over or when its cold. I used to always wear them, but I suppose laziness has set in, at least within the confines of my own walls. If I’m not wearing those pajamas, I really like the button front BB boxers, especially for when it’s hot! I wear them with a super thin cotton short sleeve Henley. I always wear a robe though; black watch tartan wool flannel from Dad during the Winter months, and BB #1 Stripe in Burgundy, White, and Navy in vertical striped twill cotton with navy piped edging on the lapels and patch pockets, during the Summer, Spring, and Autumn – I LOVE this robe! It has a breast pocket – for my cotton handkerchief, or for my pen/pencil for crossword puzzles. My Dad used to keep cigarettes in his, Grandfather kept his Billiard pipe in his, with a little pouch of Captain Black tobacco. Good memories. The slippers with the actual heel are the preferred ones, in dark brown. They’re called Hercules slippers, if memory serves. I wear them, I’m 32, and have been wearing them since I got my first pair at 18 – before that I had Minnetonka moccasins with shearling lining. Dad wore velvet ones with his initials embroidered on them in silver, he usually wore green ones, though I vaguely remember a burgundy pair at some point. Grandfather wore mule slippers with a heel like a dress shoe, in suede.

  40. And this pretty much illustrates the difference between preppy and WASPy. Unfortunately, I can’t remember whom I’m plagiarizing here: “Nudity is WASPY but not preppy.”

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