5 Pairs of Pajamas That Are Worth the Upgrade

The last frontier of thoughtfully considered wardrobe staples.

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Weird question: What do you wear to bed? As in, to sleep in. Have you thought about it much lately? I hadn’t given my bedtime attire even the slightest consideration in years and years and years, until a friend gave my kids the most incredible pajamas ever—Petite Plume, I have mentioned them before—and suddenly that was all I could think about. Specifically, why was I so delighted by my children’s pajamas but completely negligent when it came to my own? And was it worth reconsidering this aspect of my bedtime routine?

My initial theory was that what you wear to bed is usually some form of arrested development. And by that, I mean once you get into the self-determination phase of pajama wearing—which for me was in high school, as my mom bought me whatever styles she preferred when I was a kid—you tend to settle on something and then basically never think about it again.

For reasons I do not understand to this day, my go-to bedtime uniform in high school and college was a pair of silky sleep shorts—which I referred to as “tap pants”—that I would buy on clearance at Victoria’s Secret and pair with a cotton shelf-bra camisole or a Hanes classic white tank top, which I bought in six-packs. Eventually, once I started living alone, I became completely unbothered with night clothes as a category. Though, I had a handful of threadbare vintage T-shirts and the aforementioned high school sleep shorts to wear when traveling with friends who didn’t necessarily want to sleep next to me in my unclothed state.

And so the years passed.

Like, years and years.

But then one day, I realized I needed something more. Dare I say it: Full-on proper pajamas. Part of it was the aforementioned jealousy of my children’s adorable jammies—in addition to the (very expensive but insanely adorable) monogrammed Petite Plume set, my kids also like Nights by Wilder (which can also be worn out and about) as well as the more casual Tea Collection styles and Owlivia cheetah pajamas—and part of it was realizing that there were still a number of nights in my future when I’d have to leap out of bed and attend to a small kiddo on the other side of the house. And frankly, it’s too cold to be running around starkers in the middle of the night.

So I started searching (and shopping) for proper pajamas. This is what I’ve found after two years of testing. May they spark as much joy for you as they do for me.

Eberjey Gisele PJ Set ($128)

If I were a betting woman and pajamas were gymnastics, I’d say that Eberjey’s classic Gisele set would be a sure thing for the all-around gold medal. They are wildly soft and a little slouchy, and while I know the description says “hand wash,” I can assure you that my pair has been thrown into our washing machine a thousand times and is still perfection. I like a dark base color for my pajamas—ahem, black, always—but they come in navy and ivory and dusty lilac. Plus, if you loathe pants and prefer shorts, Eberjey makes that too, as well as a sleep-shirt iteration. Also, if for some random reason I’m not feeling the top of my set, I will wear the pants with an old American Apparel black tank top, and the combo still looks nice.

Desmond & Dempsey Soleia Set ($155)

Fashion people who love Molly Goddard (me!) will also probably adore this line she created with her husband and named after their grandfathers. I personally love the brand’s Soleia set, which was one of the first prints the designer and her husband created and gives me straight-up The White Lotus vibes. (You can hear the theme song now, right?) Also, I love shorts, as we discussed earlier, so no duh I like this style. The short-sleeve tiger set is up there for me too, and there’s a flared iteration that feels very fashion.

Petite Plume Luxe Pima Cotton Astaire Pajama Set ($118)

I thought that Petite Plume was too Connecticut for me at first—not a knock; it does heavenly ginghams and stripes—but then I saw its Astaire sets, and I simply swooned. These pajamas are impossibly luxurious, the fabric is simply delicious, and the Old Hollywood piping makes me feel like I’m doing some sort of Lauren Bacall cosplay in the very best way possible. (Or maybe that I’m an extra in a Wes Anderson film? Unclear.) I wear these pajamas on a regular basis and cannot wait for the holidays, as I’m planning on finally buying the spirited family set that I have secretly dreamed of for several years.

Parade Super Soft PJ Set ($50)

I’m a huge fan of everything Parade is doing—the brand’s all about super-comfy fabrics, size- and gender-inclusive styles, and sustainable materials—plus there’s something so peaceful and chill about its minimalist long-sleeve pajama set. It’s available in XS to 3XL, comes in a few colors, and is made out of Tencel, which is a really dreamy material that’s softer than cotton and more sustainable to boot. To me, these pj’s are very Gwyneth Paltrow in ’90s Calvin Klein or something her character Estella in Great Expectations would wear (albeit in green).

Stripe & Stare Biodegradable Slouch Top ($98) and Bikini Briefs ($60 for 4)

Old habits die hard, and sometimes I still can’t be bothered to wear sleep shorts or pants. I also love Beyoncé’s “Single Ladies” video. Sometimes these two facts combine, you’ll find me in a look that pays homage to both ideas: A fitted, stretchy, wildly soft, long-sleeve T-shirt from my beloved British brand Stripe & Stare, paired with its equally cozy briefs. And yes, as the name indicates, you could bury the top in your backyard, and it would completely break down in approximately six months, but honestly, you’ll love it so much that won’t likely be an option for you.

ON A SIDE NOTE: In 11 days, I’m going to hit my 365/365 goal for working out, and I want to celebrate with a giveaway of some sort. I’ve been thinking about what that should include and would love to hear your thoughts. What would feel meaningful? An Apple watch? Jumpsport trampoline? A subscription to The Ness for a year? A week's worth of my favorite workout pants from Free People? Would you rather have one GRAND prize or a handful of smaller options? Please let me know in the comments below, if you have a moment!

As always, thank you for being here, and thank you for sticking around. If you have any questions or concerns, or want me to touch on any topics in particular, I’m all ears. Leave a comment on Hi Everyone’s Bulletin or DM me on Instagram—I’m @hillarykerr—my inbox is always open!