Pajama Party: Silk Pajama Shirt, Skinny Black Trousers, Black Leather Motorcycle Jacket, Slip On Smoking Shoes, and Burgundy Wide Brim Fedora

I can’t remember the last time I tried to pass on jammies as outside clothing (other than on my weekend trips to Duane Reade), but who am I to stand in the way of a fashion trend that promotes comfort? [Much like my obsession with the athleisure trend]. I’ll be the first to admit that I’m not quite daring enough to wear a full set of silky pajamas with a pair of heels to dinner (kudos to those who pull off the look), but I’m all for pairing a silky pajama top or bottom with other tailored pieces to refresh my current wardrobe. After all, the key to any great look is knowing how to strike the right balance.

A few weekends ago, I was stepping out on a rainy Saturday afternoon to run a few errands and for some catch up time over coffee with some friends I hadn’t seen in awhile. Due to my usual reluctance to get dressed or leave the apartment on rainy days, I opted for an outfit that came closest to wearing sleepwear – a silky black pajama shirt with white contrast trim (that SDP and I found during our usual internet scouring for new trends ), my brand new black with syrah pony calf hair smoking shoes from Matt Berson (for a real “loungey” look) and a slouchy black leather bucket bag. To keep things from looking too sleepy, I wore a pair of skinny black ankle trousers and my favorite black leather motorcycle jacket. Finally, for some coverage from the rain, I topped the look with a burgundy wide brim fedora (which just happened to compliment my shoes).