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Fashion Dilemma: What the Heck is ‘Dressy Casual’?

via flickr user kenmat

With our office holiday party approaching this Saturday, I was excited about doing some shopping. I have this disease where I really like to get all stressed out about getting a totally new outfit for each different social engagement. It’s maddening, but it’s also sort of thrilling to go to every single store in Grand Rapids looking for the perfect dress and accessories– yes, I know I’m slightly nuts, but it’s just something I do. So, imagine my extreme delight when I found “it”: a gorgeous purple dress on sale for– get this!– $20! Amazing find. And then. I get an email. Subject line: “Dress for Saturday Night”. Contents: disturbing. –”For those of you wondering what to wear Saturday… dressy casual. No need for a ball gown or tuxedo.” Followed by a smiley face. Smiley face!? I just lost my mind looking all over for this dress that isn’t at all casual, mostly dressy, and bordering on formal– and now you’re telling me “dressy casual”? What even is that?

You know, I get that it can be difficult to know what to wear in certain situations. In this situation though, a gathering of colleagues at lovely venue in the evening, I thought for sure cocktail attire!

The “what to wear” email, I’m guessing, was prompted by some lazy dudes in our office who can’t possibly wear anything but grungy jeans. C’mon fellas– at least put on a nice jacket!

So, I’m going to need your help here– Firstly, what do you think “dressy casual” is? Secondly, will I be way over-dressed in this?

And finally, am I being way to neurotic and should just wear the dress and shut up? Haha!  Any and all comments welcome here.

Have you even been in a situation in which you really had no idea what to wear? Or in which you were way over or under- dressed? How’d you deal?

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