By Elyse Maloni
Updated Jun 06, 2015 @ 1:30 pm
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Ever since pajama-inspired separates hit the runways years ago at Marc Jacobs, Gucci and just about every major designer show, we've become a bit notorious for wearing our favorite pajama shirts to nice restaurants, fancy parties, the office, and essentially anywhere you think you shouldn't. Perhaps it has to do with our deep admiration for Greta Garbo and women of her era, who were encouraged to wear sleek and silky sleep sets for nights out. Or, maybe it's our desire to bring a little midweek slumber (albeit, a glamorous one) into the wardrobe fold. Whatever it is, we couldn't be more excited to share our favorite sets that are distinct in their own ways, but that all deliver maximum comfort.

For the Office


Pair these ultra-chic Piamita pieces—the contrast piping really pulls the look together— with Prada's jacquard pump for a glamorous version of the classic bedroom slipper. Add a classic bag in a dreamy hue, like Coccinelle's. Tightly tuck in your shirt and pin your hair back in a low bun for a professional take on the pajama trend.

Shop the look: Piamita blouse, $287; Piamita trousers, $199; Coccinelle bowling bag, $350; Prada jacquard pump, $520;

For the Weekend


Lazy weekends with no plans are the ones we look forward to the most: staying in bed longer than necessary, leisurely reading the newspaper, and meeting friends for brunch. Enjoy those weekends in something simple and sweet, like Gap's floral short set, that we'd elevate with Valia Gabriel's slide sandals and Jade Jagger's arrow studs. Finish off the look with messy bed-head.

Shop the look: Jade Jagger arrow studs, $93; Gap pajama shirt, $35; Gap pajama shorts, $25; Valia Gabriel sandals, $152;

For an Evening Out


Black-tie pajamas are the ultimate style statement, dripping in confidence and elegance. Because it's also a major fashion risk, test this trend out on date-night first (versus a gala) or when you're feeling fashionably fearless a la Rihanna. Choose a menswear-inspired silk set in a rich, saturated color, like Olivia von Halle's plum pajamas. Wear the silk shirt long and loose with a chain belt to accentuate a sexy silhouette. Throw on a pair of matching metallic heels, amp up the smolder with a lot of kohl eyeliner, and enjoy an old-fashioned night out.

Shop the look: Olivia von Halle silk pajama set, $540; Chatelaine Charm Belt Company belt, $213; Cos heels, $225;