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How to Wear Your Pajamas Everywhere (and Still Be the Best Dressed Girl in the Room)

Fairchild Archive

Fashion reporters had a field day last September when Rachel Roy walked the red carpet in Manolo Blahniks and a slouchy sleepwear set. We found it refreshing to see the emerging trend (which has populated the runways since Dolce and Gabbana's Spring 2009 show) fully realized and executed to perfection. In a world of bandage dresses and uncomfortable shoes, why shouldn't we embrace this relaxed style?

Wearing pajamas outside the bedroom is not as tricky as it first appears. We've demystified the look with five fool-proof rules:

1. Mix Textures. Juxtaposition is the key to pulling off this ensemble. Silky menswear pants are best with a structured blazer or chunky cable knit; if you wear the matching top (like Rachel) be sure to include heels and bold jewelry. Avoid T-shirts unless you use them as thin layering piece, otherwise it looks like you just woke up.

2. Don't Neglect Your Makeup and Hair. A polished beauty look has the power to make the most informal of pieces look fancy. Showing up with a slicked back ponytail and killer smoky eye keeps your ensemble from reading sloppy.

3. Scared of Separates? Try a Slip! If you just aren't ready to publicly appear in printed draw-string pants, a slinky slip dress is a great way to dip your toe in the water. Layer one under an over-sized cardigan or a see-through dress.

4. Sweatpants Aren't Just for the Gym. Delicate fabrics are better suited for an evening party, thick cottons for a causal day out. Stick to a skinny silhouette and pair with patent flats and layered knits. If you need to dress them up for dinner, switch to pumps and a sparkly top.

5. Don't Think of Them as Pajamas. This might be the most important rule of all. Once you've made the conscious decision to transition a bedtime item to your regular wardrobe, you can't compose your outfit with an "I'm wearing pi's" mindset. Don't let labels trip you up.

Running low on day-worthy night clothes? Click through the slideshow for some of our top picks, available online now:

A set of menswear-inspired pinstripes offers multiple outfit options. Mix and match the separates or wear them both with strappy stilettos!

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