23 Pajamas That Make Going to Bed a Genuinely Stylish Pursuit

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There was a moment some years back—from 2015 to the beginning of 2017, more or less—when it was not only acceptable to wear pajamas outdoors, but highly encouraged. The folks doing the cheerleading included Dries Van Noten, Boglioli’s Davide Marello, Gucci’s Alessandro Michele, and Fendi’s Silvia Venturini Fendi. On their runways, these designers showcased the best silk separates, flannel sets, and dress robes. The styles that were normally intended for the boudoir stepped into the spotlight, bringing loungewear to the forefront pre-all things sweats and elevated trackies.

The look certainly wasn’t new among sartorial circles. Hugh Hefner, Julian Schnabel, and other men of high stature and egos to match seldom wore anything but pajamas. It signified power, wearing a silk two-piece with a robe to an event where other attendees donned a suit and tie. The cojones of it all was indisputable.

Want to follow the example of these high rollers? We have a range of tony pajama sets that’ll definitely do the trick. Just pair them with dinner slippers and a whole lot of chutzpah, and consider yourself minted. But if you’re like me, we also have some comfy, cozy options to snuggle in. Either way, the best pajamas below are ready and waiting to be purchased.

Pajama Set

With classic pajamas like these—and at affordable prices, too—Hanes is definitely the gift that keeps on giving. A cotton and polyester blend is keeping them breezy, too.

Scotch Plaid Flannel Pajamas

As sturdy as any of the best outdoor-ready flannels the brand churns out, and as handsome, too. Something about flannel just feels right.

Night and Day Long-Sleeve Pajama Set

This cotton pajama set proves that Hanro's Night and Day collection certainly lives up to its name. Subtle piping detail keeps it timeless, while also creating some edge in the contrast.

Buffalo Plaid Pajama Set

These pajamas are a standard choice, so go ahead and check yourself. Plus, with this price, you can stock up on as many styles as your heart desires. Go wild.

Windsor Tartan Pajama Set

We love these PJs so much that we waxed poetic about them earlier this year, but the short story: These are soft as hell, perfectly chic, and they make for the ultimate gift.

Pajama Set in Cotton Poplin

These are the quintessential, timeless pajamas that you can do anything in. Sleeping is certainly the best option, followed by lounging, but, hey—nothing's stopping you from going down to the corner store in these to grab a late night (or early morning) bagel.

Bamboo Pajama Pants

The perfect combo: these soft, stretchy bamboo PJ pants, the matching shirt, and a night in. We're even one-upping that with the newest Cozy Earth essential: The Cuddle Blanket.

Monogram End-on-End Pajama Set

If you want to pony up, Ralph Lauren's Purple Label offers a premium cotton set that's a show horse. Or, in layman's terms, it's just a great pair of pajamas that feel as deluxe as deep slumber deserves.

Pajama Button Up Shirt Set

Following the hype of brand's beloved cashmere, Naadam's pajamas are worth hitting the snooze button for. They're super soft, giving you cozy comfort all night (and day, we don't judge) long.

Second Skin Tee And Pant Set

Tommy John does relaxation the right way. There's a reason why this set is dubbed the "Second Skin" set. It's like you're sleeping in the nude. Almost.

Pajama Sleep Set

Knit jersey with a touch of stretch is exactly what you want when you think about cozy pajamas. Comfy and casual—everything pajamas should be.

Animal Print Pajama Set

The kind of pajamas for a man who never wears something unfashionable—even in bed. If you want style and quality you can count on, you can never go wrong with Desmond & Dempsey.

Charles Washable Silk PJ Set

If you haven't tried Eberjey's pajamas then you're missing out. And if you haven't tried its washable silk pajamas, then you're really missing out.

Herringbone Stripe Pajamas

Pajamas for the man who is no stranger to a good nightcap before bed. Subtle stripes give just a bit of edge to the pair.

Cropped Basic Supima Cotton Pajamas

If you tend to get warm when you sleep, this soft shirt and shorts set is for you. The Italian brand is bringing high quality at a price you can get behind.

Boxer Shorts Set

A set that doubles as basics you can wear every day. Throw the tee under a shacket and the boxers under some joggers. Now that's some bang for your buck. Don't worry, we won't tell.

Steiner Set

UGGs is more than just its fuzzy slippers, people. The brand's signature cozy construction takes the form of pajamas. And it's no different. Except utter relaxation when you put these on.

Henley Pj Set

We love our henleys, so what's better than one you can sleep in? A soft jersey fabric and drawstring waistband deliver premium comfort so that you can get the deepest of slumbers.

Washable Silk Short Set

If you haven't tried washable silk, we're about to convert you. The material is naturally thermoregulating, ensuring you maintain an appropriate temperature all night long. And, true to the name, just throw them in the wash, and they are good as new.

Jammie Essentials PJ Set

There's nothing like the silky smooth feel of P.J.Salvage's sets. Something about the blend of French terry knit crafts a style that you won't want to take off.

x Birkenstock Pajama Shirt

One of the coolest—and most unexpected—collabs of late was the union of Tekla and Birkenstock. This cotton-poplin shirt is ultra lightweight, and you can snag the matching pants to complete the set.

Washable Silk Button Down Short Set

Maybe you are curious, but aren't yet quite sold on washable silk. If that's the case, this affordable set from Quince won't make you shell out the big bucks for dependable quality.

Silk Jacquard PJ Top

Fleur du Mal makes pajamas that are straight up royalty-ready. Case in point: this luxe silk satin top with tonal brand monogramming. Choose between the matching pants or boxers—whichever floats your boat.

Why You Can Trust Esquire

We’re not going to tell you something is great unless it's actually great. Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams.

Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.

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