Pajamas Are the New Uniform for the Undone and Unbothered

Perfectly dressed and already half-asleep, in the best way. And if the men are in silk sets, best believe the women can wear them better. Here’s how.

By Sean Castelo III July 07, 2025

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Is it bedtime or business class? Aperitivo or actual agenda? Men’s Fashion Week S/S26 said: why not all of the above. Pajama dressing—crumpled, confident, and completely unbothered—has stepped out of the bedroom and into the streets, looking like it woke up fabulous and effortless (because it did). And nothing felt more Italian.

^{The look of staying in, worn to go out}

Ferrari doubled down on its reputation for speed and seduction. Printed silk shirts, relaxed trousers, and a pinstripe look so laidback it could win the Formula 1 trophy while still in REM sleep.

Emporio Armani followed with its signature soft tailoring: chiffon shirts billowing like Roman curtains, silky pants pooling with purpose, the whole ensemble crumpled but considered.

^{Pajama dressing is Nothing rushed, nothing random.}

Dolce & Gabbana, never one to be subtle, titled their collection “Pyjama Boys” and meant every word. A clash of stripes, boxy jackets, and drawstring trousers gave the whole thing a post-coital, pre-lunch flair—half dandy, half daydream. Throw on a heel, and suddenly the bedhead’s a style choice.

How Women Can Wear Pajama Dressing Without Looking Under-Dressed

^{these Off-duty silhouettes, fully aware of their effect}

Treat Satin Like a Statement

Swap the standard blazer-and-trouser combo for a matching silk set. Whether printed or monochrome, the key is in the fabric. It should look indulgent enough to suggest you meant to wear it out—even if it feels like you didn’t.

Actually Accessorize

This look lives in the details: a sharp heel, a structured bag, or jewelry that feels deliberate. It shifts the tone from morning-after to midday power play—no caffeine required.

Redefine “Put Together”

Unstructured doesn’t mean unfinished. Let the silhouette stay soft, but bring definition through polish: a bold lip, a slick bun, or tailoring somewhere in the mix (even if it’s just the collar).

On this season’s runway, an outfit is built for the indecisive: caught between meetings and mimosas. But that’s perhaps the point. The work-play dilemma collapses in clothes like these. Pajamas and pajama-like sets now move differently. Wrinkled on purpose. Intentionally off-duty. Less about dressing down, more about dressing out of reach.

Photos: FERRARI, EMPORIO ARMANI, and DOLCE & GABBANA