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Fashion

POSH & PREPPY PAJAMAS FOR ANY SEASON

“The best gifts are little luxuries the recipient would never buy for themselves.”
– Town & Country, in praise of LAKE super-soft Pima pajamas.

Is there any aspect of life that wasn’t affected by the pandemic? One perhaps unexpected thing it did was to shine a spotlight on…yep, pajamas. As a result of people working from home, the popularity of PJs skyrocketed. We spanned the gamut, from just working all day in our pajamas to creating the new hybrid look of dressing business casual from the waist up. . . while featuring your favorite sleepwear below camera. And, we started placing more value on comfort, fueling the focus on comfortable, fashionable pajamas and a willingness to spend money on them. So, it’s no surprise that pajama sets that express style and give us a feeling of being put together are on the rise. In this blog post, we’re going to give you the lookingGLASS picks for the perfect pajamas from our favorite nightwear brands.

Let’s face it, nobody craves a great night’s sleep like busy moms with young kids. But, most of us probably don’t think about the connection between our sleepwear and the quality of our sleep. Actually, according to experts, the two are related. Who knew that wearing binding clothing at night can actually inhibit melatonin production, which affects your sleep cycles. Yikes!

When you’re in the mood to buy a pair of new pajamas, the first thing you’re probably thinking about is the season. Is it wintry outside, hot, somewhere in between? Or constantly transitioning back and forth from one to the other? Do I need long sleeves or short? Tank top? Long pants or shorts? What fabric? What style am I in the mood for? Preppy, posh, cute, comfy, loungewear? Maybe something I can run a quick errand or pick up the kids in? Or, hey, what about a cute nightshirt?

Most of us have a preference for certain fabrics. Do you love natural fabrics or maybe you’re trying to be more conscious about sustainability with your buying choices and want to explore the newer eco-friendly fabrics?

Sure, when it comes to choosing your sleepwear, comfort is key. But that doesn’t mean you can’t treat yourself to comfort and style! The goal at lookingGLASS styling app is to show you how to develop your wardrobe to assure you have both—down to your pajamas! Regardless of your preferences, there are pajamas in a cut, style and fabric that you’ll swear were designed with you in mind.

Classic Preppy Pajamas

Here are our lookingGLASS stylists’ picks for great style and comfort for chillier weather, starting off with some fabulous long sleeve pants PJs from brands like LAKE and Target.

For a classic preppy aesthetic, we love these poplin PJs from LAKE, featuring a long sleeve, button up top in classic navy and white stripes. For a softer look, Eberjay offers a similar style with a drapier look and a ton of colors to choose from.

Woman wearing blue white striped classic pajama set
Woman wearing light pink preppy classic pajama set

The Boyfriend

If the boyfriend look is more your style, you’ll love these traditional men’s cut pajamas from J. Crew, HERE, featuring breast pocket, notch collar, piping and elastic waist. And if you’re mad for plaid, you’ll love the roomy L.L.Bean men’s cut HERE.

Posh Pajamas

Cute lounge sets and sleepwear for ladies have always been in style. But although most of us have probably taken this sleepwear icon for granted, PJs have a history that might surprise you. Take a little peak at the PJ backstory.

At the beginning of the 20th century, pajamas were introduced as women’s sleepwear and, by 1920, were trending as at-home evening wear. By 1916, pajamas had made their way into women’s closets, thanks in part to a couple of hit Billie Burke films at that time (yes! The same Billie Burke of Glenda, the Good Witch of the North, fame in The Wizard of Oz). In yet another pajama power play, Bette Davis caused a fashion revolution in 1943 when she appeared in her husband’s pajama top as her sleepwear in the film “Old Acquaintance.” The morning after the movie opened, the iconic I. Magnin luxury department store sold out of men’s sleepwear, all of it sold to young women.

Fuzzy and Stylish

You can always count on Target for super cozy and casual with affordable prices. We love these feather yarn pajamas from Stars Above, and if you don’t own a set of these, where have you been? Just looking at them makes you want to curl up with your favorite book and cup of coffee. An added benefit for these cozies is that, in a pinch, you could throw on your favorite sneakers and run an errand without having to change into “street clothes.” And nothing will make you feel more like you woke up at your favorite ski-in ski-out chalet than these cute cuffed thermals with the Henley-style top. Aaand, we’re thinking these could easily double as long underwear when the thermometer takes a sudden plunge!

Nurture your Natural Side

If the call of the wild is your love language, check out these outdoorsy, nature lover pajamas from L.L.Bean. Casual, cozy and cute, it’s hard not to love this sleepwear. The color-coordinated Henley top features placket and inside neck lining detail out of the same fabric as the pants, pulling it all together for an elevated casual look. Check out these super cute pretty-in-pink PJs from Tommy John, featuring a big cat nature print. We can almost hear those big kitties purring as you drift to sleep in this fun set.

Continuing with the fabulous feline theme, we love these Katie Kime cheetah prints. When you slip into these pajamas, you’ll understand why some of the most important goddesses of yore are depicted with the persona of a big cat. And this is one cat you’ll be thrilled to let out of the bag!

Okay, how fun are these Katie Kime “affirmation” pajamas? Come on. “The world is my oyster?” Who could have anything but a fabulous day after waking up to that?

Streetwear Worthy

This “slouchy” PJs set from Eberjay might be our favorite for a crossover style that can go from sleepwear to loungewear to a quick dash to the grocery store. This high-style look combines a roomy drop-shoulder, slim sleeve top with Cairo style pants tied at the waist with a beautiful contrasting color oversized drawstring. The high quality, buttery soft fabric is 95% crease and shrink-resistant modal jersey. It’s easy to see yourself hanging out all day in this easygoing all-purpose pink set with short sleeves and Cairo pants.

Reader's Choice

Town & County praised Lake PJs and they weren’t wrong! There’s just something deliciously glam about this LAKE long sleeve with shorts pajama set. The long sleeves give it a sort of boyfriend feel—think Bette Davis raising some eyebrows from the big screen—the shorts give it a cutesy kick. The superior-quality poplin fabric is a great canvas for the main attraction: chartreuse. 

We can’t talk about chartreuse without mentioning its provenance in the Carthusian Mountains of the French Alps! In the late 1700s, an ancient elixir recipe was tweaked to create the French herbal liqueur we know as Green Chartreuse. Some 75 years later, it was tweaked again, and voila! Today’s Yellow Chartreuse—which btw is the gorgeous color of these pajamas! This yellow-green can be a tricky color to wear (paler complexions can look overpowered and washed out by this vibrant shade), but if you can pull it off, you’ll wake up feeling spring green fresh, whatever the season.

Woman modeling yellow chartreuse pajama set

Preppy Meets Southern

Here’s a perfect PJ solution for those hot winter nights. Yes, hot. It happens. Just ask anybody who lives in a region that has winter weather that fluctuates between cold snaps and “unseasonal” warmer temperatures when Mother Nature just can’t seem to make up her mind. This soft, silky knit tank top and long pants set is made of Peruvian Pima cotton, the “cashmere of cotton,” and offers cool to cozy comfort for those transitional nights. Speaking of transitional weather, short sleeve pajamas with long pants is a safe bet. Reach for a fabric like cotton, silk, or some of the newer sustainable, temperature-regulating fabrics, like bamboo.

Love classic gingham? Leave it to Reese Witherspoon’s Draper James brand to offer up this sweet and fresh as a farm-to-table breakfast pajama set in pink gingham. Just don’t be surprised if you wake up singing Oh, What a Beautiful Morning! 

If you want to get in touch with your inner southern belle, these preppy-meets-southern-magnolias could be the cute PJs for you. The dreamy polyester and spandex blend fabric features white magnolias on a buttery pink background. 

Katie Kime takes a southern twist on tolie with this Dallas themed pink set. 

Splurge vs. Steal

For warmer weather, who doesn’t love a pair of shorty pajamas? Can you say shorties, for short? Well, we do want to cover the long and short of it…

These three similar preppy pajama sets, all short sleeve with shorts and shown here in navy, feature classic button up style with breast pocket and contrasting piping, and demonstrate a range of fabric—and price—options. The Stars Above from Target is a great cute look in a modal blend fabric at a very affordable price. In the medium price range, you can’t miss with J.Crew’s crisp looking 100% cotton PJs, with elevated styling elements that include contrasting drawstring waist and a nautical flare. If you want to treat yourself to one of life’s “little luxuries,” why not spring for the comfort of stretch-knit bamboo from Cozy Earth? We love the variety of color options here, especially the make-you-weak-at-the-knees pomegranate. There’s a reason Cozy Earth has made Oprah’s Favorite Things list five years in a row! The list has featured best pajama brands for women, and as a matter of fact, this popular segment started out with her love for flannel pajamas! 

The Perfect Nightshirt

Or, you may want to ditch the PJs look altogether and opt for this cute nightshirt from J.Crew.

Okay, this shorter-than-most-nightshirts length featured here does conjure up the Bette Davis husband’s pajama top movie scene we described earlier, but this made-for-the-ladies version fits oh so nicely in the shoulders!

Woman modeling night shirt pajama top

Affordable Luxury

If you’re looking for a luxe look at an affordable price, you’ll love these easy glamour, silky satin look shorty pajamas from Ekouaer, featuring a scoop neck, pullover top and tie-string shorts, and available in a variety of colors and a cute print option.

Our Favorite Pajama Brands . . .

  1. LAKE – Best overall for comfort, quality and price. We love that they have lots of fabric and print options.
  2. Tommy John – Material is a dream, stretchy and soft (like your favorite underwear from college that has lost all the elastic!). Great first-order discount and sizing guide.
  3. Stars Above – Affordable – half the price of other brands -– and convenient (already on your Target run!). Great selection of prints, including options like Christmas pajamas.
  4. Cozy Earth – Bamboo fabric can be cooler than cotton. Unique 100-day free night sleep trial guarantee. Basic neutral, solid colors and comes in tall lengths. Also offers joggers, sweatshirts and bedding.
  5. J.Crew – Always reliable for that classic preppy put together look (including monogramming option!) that’s good when you’re lounging around with the gals on a sleepover. Offers extended sizes.
  6. Draper James – Another great preppy brand, with a soft, feminine touch. Not as many options, but at around $70, and more affordable than J.Crew.
  7. Eberjay – So-comfy jersey fabric and wide price range ($50-150). Some are hand-wash only. Convenient on Amazon.

Other great choices include:

Katie Kime – Playful and fun. An Austin local.

L.L.Bean – Flannel lovers go-to. Reliable quality and style.

Lunya – When you want to splurge on washable silk!

Ekouaer – Luxe look and feel of silk without the $$$ price tag.

At lookingGLASS, we hope you’ll remember to treat yourself to the “little luxuries,” and we’re here to help you look and feel great in what you wear—even in your jammies! 

Curious about our other services? Find everything you need to know here.

Send us your selfies for instant outfit feedback! Simply download the app here, let us know a little about your event and snap a few pics. We’ll answer your style questions and help you tweak your look until you love it!

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Hello, I’m Lana
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Hello, I’m Lana

My passion lies in helping people. I really got into this when my friends and I started having kids. We all felt a bit uncomfortable in our new bodies, and the clothes we used to wear didn’t quite suit our new lifestyle. The app was created so that everyone could have the help of an expert, at an affordable price. When we look good, we feel good.”

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