Does This Grey Dress Have An Inner Evening Diva? Fashion Advice Needed

When I'm getting ready and proclaim "I don't have anything to wear," I'm slightly exaggerating (as I think most of us are when we make this statement). I have lots of things to wear, I'm just lacking in the creativity department on  knowing exactly how to pair certain things with other certain things.

Earlier this fall I bought this dress:

Although I didn't buy it for a specific event, I thought it quite versatile and it fit me well.


Now I know how to wear this dress safely in the day time with its matching belt - very safe and a little office looking.  I have a hunch though that if I dig a bit deeper, this dress may just have an evening diva lurking within its seams and I could use it for the holidays somehow. (or is this type of gray dress only for the day?)

How to get it there? No clue.  I know it has something to do with what I wear on my legs, definitely footwear and of course jewelery, but when I put all of that together, I get a bit confused of what to put with what.  So here is what I have:

For my legs:

Option #1

Option #2

Option #3

Option #4

Obviously the gray tights would keep everything streamline, but are they too casual? If paired with black tights, is it a harsh contrast between legs and dress?

 Belts:

Option #1 - grey belt that when buckled has way too long of an end, so probably not an option ... I should probably get rid of it come to think of it
Option #2 - Black wool tie belt
Option #3 - wide black leather belt
Option #4 - matching grey tie belt
Option #5 - Black tie belt, satin on one side
Option #6 - skinny purple braided belt
(I know I'm missing a skinny, sparkly evening belt)

And finally, if I haven't lost you, the shoes:

From left to right: grey suede pumps, NYC pumps, purple pumps, black ankle boots ... and I have black pumps too (not shown).

So as you can see, there is a lot that goes into it. I may get as far as the right shoes, but then don't think the tights match ... and then the belt, don't get me started.

Is this dress to daytime? Can I pull it off for an evening dinner?

Would love to hear your suggestions (that means you Rebecca .. I mean anonymous!)

P.S. Reminder: lots of great stuff planned for next week ... including Holiday Fashion Must-Haves (don't worry I recruited some help).