People who trot out the old adage "one can never be too overdressed" have never rolled up to a dive bar in a gown. For me, being overdressed is as mortifying as realizing your skirt has been tucked into your underwear for the duration of the night. So when it comes to holiday party outfits, simple, black ensembles are my go-to. Not to say that this minimalist color choice is overtly casual, but it solves the crux of the problem of overdressing, which in my opinion is looking like you tried too hard.
When done right, minimalist dressing looks completely effortless. (Of course it isn't, alas, what is this days?) When there are few bells and whistles to distract, details like fit and fabric are thrust into the spotlight, making them infinitely more important. If this is the path you've chosen, you can't get away with buying a top two sizes too big or a slip made from a shiny polyester blend. Each item actually has to look like it was not only tailored to you but actually designed for you. And the fabrics have to look expensive, which is not to say that this whole vibe has to actually be expensive. In fact, it's totally doable on a budget, as long as you keep fit and fabric front of mind. Here are a few of my favorite examples to save you from the plight of wearing a gown to a dive bar.
Slip Dress + Croc Embossed Boots
Eschew the sequin explosions for an achingly simple slip dress. Rather than pairing it with (impractical) heeled sandals or pumps, choose a croc-embossed boot, preferably one with a lot of slouch that hits just below the knee. All the better for concealing a thick and cozy pair of socks which will make the trip from the train/car to the party far more bearable. Add a longline knit cardigan in a chunky weave like mohair to counterbalance the sleek dress and, of course, keep you warm when the bar is inevitably near a draft. Finish with a sleek necklace.
Suit + Brogues
What's cooler than wearing a suit and brogues when everyone else is in a mini dress and heels? The key here is to show a bit of skin, and add some unique accessories. Strike a balance with the fit, for example if you're going for a slouchy blazer silhouette, make sure the trousers aren't also drowning you, lest you look like Tom Hanks at the end of Big. Finish with a red lip and a cool bag.
Sheer Turtleneck + Leather Pants
The wonderful thing about sheer clothing is that there is an opacity for everyone. If you consider sheer to be a fine-gauge knit through which you can detect the color of a bra, that's great. If you prefer to push the envelope with an almost transparent iteration, that's also great. Either way, team it with demure underpinnings, a high-waisted leather pant, quirky earrings and a robe coat or longline blazer.