We’ve all received one.  The invitation to a birthday party, benefit, or holiday soiree with a cleverly worded dress code that leaves you confused and clueless?  I’ll never forget the first time I encountered one.   I was a college junior dating a man who had graduated, and we’d been invited to a dinner party where the invitation read “casual chic.”  As a student, the chicest things I owned were my grandmother’s pearls that I wore with an over-sized grey Champion sweatshirt baring my sorority letters (oftentimes with a peter pan collared blouse underneath – yikes) and the houndstooth blazer I had purchased for a summer internship interview.  Somehow I knew neither would work but I had no idea which direction to go.  I still remember what I ended up buying – a simple black shift, black pumps and a fuchsia blazer (and yes I wore the pearls).  The outfit was safe and I blended in with women ages twenty to seventy, but wow was it B-O-R-I-N-G.

Therein lies the problem: nebulous wording such as “casual chic” or “holiday festive” scares you into dressing like a sartorial wallflower.  Or even worse you end up guessing completely wrong.  As one friend commented, “what if you show up biker bad-ass to country club casual?”

Having a few decades of parties under my belt now, I’ve adopted a formula that seems to work fairly well and helps me avoid making the “what are you wearing?” call to the hostess.  If the event in question could lean either casual or dressy, I’ll base the outfit in classic pieces like a trim blazer and velvet pointy toe pumps and finish with more modern elements like leather pants and a chunky crystal necklace.  This not only helps create a balance between dressy and casual, but it also injects a healthy dose of personality into the look.

And if you have an occasion you know will be dressy but you are unsure of how dressy?  Always skew to the most formal level you think possible.  Trust me when I say being over-dressed is a far better fate.  The invitation to the benefit my husband and I are attending this weekend reads “cocktail attire: Hollywood Glamour encouraged”.  Old Hollywood?  New Hollywood?  Left of Audrey?  Right of Marilyn?  The possibilities are endless.  Just please no Kims or Chloes.