Love the last one. There is a reason the LBD is such a staple. Search high and low for one that flatters you and you can wear it for years. Add some sparkly earrings for the party and get made up at a beauty counter if you’re up for it (always ask the most natural-looking salesperson). You can surely get away with black ballet flats or low heels.
Consider a black pant suit with a satin shell.
I found a fantastic black dress that accentuates my breasts and nips in at the waist and looks really sexy on me. I am excited about my dress and hopefully the party will be fun.
Yay!
Awesome! See, now you can wear it to just about anything but weddings - it’ll be a real fashion workhorse for you.
So, what about the shoes? I say silver! Or red. It *is * a holiday party…and you can always use a pair of red shoes…
I was digging through my closet and I have a choice between silver strappy heels or black knee high boots. I was thinking boots simply because it is SO COLD in NYC but the silver shoes would be very cute. Hmmm, decisions decisions…
I’m glad you found the right dress! I love the feeling of knowing you have something you feel happy in and not being able to wait to put it on and hit the party. Have fun!
ETA: and go for the silver strappy. You can always wear boots and change when you get there.
Silver strappy’s my vote too, but you could always try the whole outfit on with the boots before you make up your mind.
Ooh…do the old “shoe on one foot, boot on the other, stand profile to the mirror on each side” trick and see which looks better. I suppose you could wear some nice black opaque tights (erm, pantyhose?) with the strappy shoes if you want warmth.
Black tights with silver sandals? No no no no no no no no no.
A thousand times NO.
If you wear the silver shoes, get some dangly silver earrings (Claire’s or similar), maybe a silver bangly bracelet as well.
I say black clutch purse, nude hose with the silver sandals and those two pieces of jewelry (and any rings you want to wear). Plus, another coat of mascara, and perhaps a slightly deeper shade of lip color–Rowr!
Thanks for all the help! Now the only question left is my hair. I have long, wavy red hair that falls below my shoulders. Generally I am a ponytail kind of girl, not only because I do a lot of walking in my commute but also because I wear a headset all day. I would like to do something simple but appropriate with my outfit. Do I wear it up or down? Any recommendations for simple hairstyles that would work for a cocktail party?
Just to make sure you know, the answer is no.
Maybe black hose (tights?) and silver shoes are the Thing over in Ireland–who knows?
You could wear it up in a different style or really wow 'em by wearing it down…
How far removed from your office persona do you want to go? I think you might be more comfortable with it up, since you wear it up a lot. Try a French twist or even a braid. If your hair is at all curly, you can do the wisps thing to soften the look.
We want pics!
Im not looking to go too far from my office persona, but somehow I am not seeing my bright red ponytail holder going over very well with my whole dress/jewelry thing I’m going to have going on tomorrow night. 
I guess I just want to take the opportunity to play dress up a little bit since the occasion seems to call for it and since it is at a fancy Westchester country club I don’t want to be too out of place if it ends up being a really dressy affair. I have never been to one of these things before and I am very excited but also nervous. It is a very small company (we have about 30-35 people in our NY office) and most of the people who work here get paid incredibly well so I would not be suprised to see Chanel and Armani being the attire of choice with a vast majority of the people there.
Also since I am going without a date I kind of want to look sleek and sexy so that all the mother hens in my office don’t do that, “Poor dear! Couldn’t you find a man interested in coming with you tonight?” thing that judgemental older ladies in the office tend to do. I would rather them focus on the fact that I look faaaabulous instead of the fact that I am there alone if at all possible.
Then do Y2K’s version of Power Hair–gleaming, clean, shiny, loose curls that look like you just tumbled out of bed…Work it, girl!
don’t forget some nice perfume–but keep it light.
You can just go with a simple knot in your hair that starts with a ponytail but ends up looking sleeker. Here’s a video (ignore the product suggestions):
http://www.luscious-locks.co.uk/2007/09/14/chic-and-simple-hair-knot/
You can always pull out a few strands around your face and curl them into ringlets.
To be honest, long wavy red hair sounds absolutely gorgeous . . . why not wear it down?
Can we see a pic?
Gestalt.