Why Stylish Men Shouldn’t Neglect Their Night Outfit

Welcome to Condition of the suitnew Robb’s Report series, in which writer and menswear stylist Caroline Reilly examines the outfit choices of candidates, pundits, and other influencers. Whether it’s an ode to the outgoing president’s timeless style, a fantastic list of items we think would be better suited to the distinguished figure, or just sage advice on how to elevate your game, she’s got a lot to think about.

Much has been written about the importance of healthy sleep, the countless gadgets you need to buy, and the substances you need to use. have to avoid getting the ideal 8 hours of sleep per night. I admit I am not particularly militant about my sleep health. I have always had a relatively easy time napping and apart from spending an hour or two each night reading some broken Scandinavian thriller and Always when it comes to having fresh flowers in the bedroom, there are a few “rules” I follow. That said, one thing I absolutely cannot stand is subpar nightwear.

Maybe it’s my Italian nature, or the fact that I’ve always been a 95-year-old woman at heart, but I’ve never been able to stomach a sloppy, oversized T-shirt or dingy flannel. I was raised to believe that what you wear to bed is just as important to your sense of style and self-respect as what you wear in your everyday life. As we explore what men’s fashion says about who men are, their inner lives, their power, their politics, I would be remiss if I didn’t take this opportunity to express my opinion on the wonders of luxury sleepwear and the depressingly rare art of sleeping in style.

Here in Robb’s ReportWe’re no strangers to the intricacies of sleepwear. My colleague Eric Twardzik has taken an in-depth look at why a flannel robe was the perfect lockdown essential — and that remains true post-lockdown, as does his evergreen analysis of the appeal of old-school dressing gowns. Classic and contemporary media are rife with exemplary sleepwear: everything from the iconic terry cloth robe and Brick’s pajama set to Cat on a Hot Tin Roof to the silk numbers in Scorsese’s film Irishmanto the flashy paisley dressing gown Ripleythe recent Netflix adaptation of Patricia Highsmith’s novel The Talented Mr. Ripley. Every moment provides us with tips not only on how to style pajamas, but also on how to wear the right pajamas. says about the man under the covers.

Make no mistake, it’s also an integral part of a gentleman’s life off-screen. Just ask menswear expert and content creator Giorgio Giangiulio. “A true gentleman takes care of himself and is well-dressed 24/7,” says Giangiulio. As a woman, I can attest to that. There are few things I despise more in a partner than when they show up to bed in something ill-conceived or poorly tailored—it shows a lack of respect for both of us. But even on my own, I believe in the ritual of men dressing for bed with the same effort they put into presenting themselves to the world.

“Night is my favorite time of day,” says Giangiulio. “When I indulge in my passions, like reading a good book, listening to music or watching old movies, pajamas mark the beginning of relaxation.” For Giangiulio, luxurious pajamas are an integral part of a nighttime ritual that also includes skin care and a fragrance that he uses exclusively at night, on his sheets. We note that this may also be a convention of our Italian heritage (I was raised to always have a fragrance that I use exclusively for sleeping).

Everything from vintage robes to silk pajamas make up Giangiulio’s nightwear collection. “For silk pajamas, I only wear Serà Fine Silk, which are definitely my favorites,” she says. “But I also like to wear pajamas and robes from Ralph Lauren and Derek Rose. Their selection of styles and cuts is exquisite and very comfortable for lounging around before bed and in bed.”

While I understand that not every man wants to wear silk pajamas or an Ebenezer Scrooge-style nightgown, the market is saturated with luxury loungewear and nightwear that will suit everyone’s tastes.

Years ago, when I interviewed actor Donald Sutherland about his fashion must-haves, he was kind enough to share that he swears by Swiss brand Zimmerli, which offers everything from modal-blend loungewear to top-of-the-line boxer shorts. Brands like Olatz (a favorite of pajama lover Julian Schnabel) and Austrian brand P. Le Moult offer traditional tailoring that’s been given a modern makeover with bold colors and contrasting piping. If you’re a fan of modal or jersey-like fabrics, look no further than Eberjey and Shan.

Italy is of course the epicenter of luxury loungewear and nightwear, with companies like Telerie Spadari in Milan and Schostal in Rome (purveyors of the papal socks) producing beautiful pajama sets, robes, and nightgowns in a variety of materials, from lightweight cotton to flannel. The former can also create a custom set in your choice of material (make sure to buy some Venetian Friulane slippers while you’re at it). There are few things sexier than a man sleeping in a simple pair of poplin boxers, like these from Telerie Spadari. At the other end of the spectrum of desire (perhaps so far away that it becomes attractive again) are Schostal nightgowns.

London is also, unsurprisingly, a great place to stock up on nightwear, given the sartorial savoir-vivre of Savile Row and Jermyn Street. Budd creates beautiful, timeless pajama sets – with details like those on the shirt cuffs – that rival most ready-to-wear men’s clothing on the market. For the ultimate in sleep luxury, a Turnbull & Asser set or dressing gown is all you’ll ever need.

For many, dressing up for bed seems like an outdated practice. The act of wearing a matching pajama set, investing in pajamas that are as well-made as a tailored shirt, and treating the man you are behind closed doors with the same attention to detail as you do in public, seems almost like an act of rebellion in these relaxed times. Giangiulio and I agree that it’s a tradition that every modern, stylish man should uphold. “You always have to be prepared for anything,” he says.

Author’s

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  Caroline Reilly

  Caroline Reilly is a New England-based menswear writer and stylist. Her work has appeared in GQ, Vanity Fair, The Washington Post, and more. Her great-great-grandfather was FDR’s tailor, and she…

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