Pajama Party: How to Take Your Pajama Pants Out of Bed and Onto the Streets

Busy Phillips, Selena Gomez, Jessica Alba, Isla Fisher, and Katie Holmes

After Stella McCartney and Diane von Furstenberg showed loose fitting, printed pajama-style pants on their respective runways for Spring 2012, the trend cemented itself for seasons to come.  Since then, everyone from Tommy Hilfiger to Dries Van Noten have shown the look. On the streets, celebrities like Selena Gomez, Jessica Alba and Katie Holmes have made wearing the trend look effortless.

But while pajama dressing sure is trendy, it may not surprise you to hear that it's not as simple as leaving the house in the same outfit you slept in.  Style, fit and fabric are all things that we need to consider when deciding how to wear pajama pants. You want the look to be flattering and streamlined, which can often be the antithesis of the way pajama pants are made.  Below, check out the looks I've gathered from Tumbler and Pinterest for some styling tips and inspiration.

Opt for a more casual look by pairing your pajama pants with a jean jacket and simple striped shirt.  If you have short legs, tucking your top into your pants helps make those gams look longer.

Tap into your adventurous side and pair your silkiest tee with some oversized trousers for something slightly “pajama-esque”. There is something slightly understated & sexy about this simple pairing.  I love the way this bright blue pair of flowing silk pants brighten up a dreary fall or winter day.  This look is also great if you've got a curvy shape- bigger hips and bust, with a small waist.  Loose drawstring pants and fitted tops really accentuate those curves for a flattering ensemble.  Large scale prints, like this paisley one, also help to play up those curves!

I will admit this trend is quite tricky to style and probably isn’t for everyone. It might even be easier come warmer weather when you can sport silky pieces with less bulk. In the meantime, go for an ensemble with pajama references, but avoid being too literal. These silk track pants give comfort without being sweats, and taper nicely at the bottom to keep your shape. When paired with a lace tee and printed smoking slippers you get a look that’s acceptable outside of your bedroom for casual weekend activities! 

Make sure your pajama pieces look purposeful; this is a classic, gentleman’s look, so stick with trousers and shirts in high quality fabrics like glossy silk or satin. When incorporating pajama pieces wear elegant accessories like a great bag, a feminine scarf, wrap sweater, or a stacked arm candy. Always opt for a sophisticated shoe like a great ankle boot and/or something with height.

The pajama pant is probably one of the hardest trends to pull off without looking like you’re about to hit the sack or just getting out of it.  It can make you look like a city girl whose effortlessly chic or a complete utter hobo. To make it look more urban than sloppy, choose a fabric that looks more luxurious like silk and if you’re going for prints, make sure that they are intricate and subtle. Some people would opt for a pajama set but if you don’t have that handy, making the look monochromatic would suffice. Add a more downtown vibe to it instead of it screaming “beach” (or “bed”) by wearing a wide-brimmed hat, gold/rose gold jewels and ankle boots.

Who doesn’t want to wear pajamas all day?! The trick to keeping the look day-time appropriate is to add a structured element, like a belt, or a blazer.