For some, this is an easy question to answer; in fact, one that is enjoyable. For others, it can be an absolute nightmare. Although you will probably be seeing family or friends that you visit with often, there are, of course, others that you have not seen in quite some time. Of course, you want to make a good impression.
Here's some ways to approach choosing the right outfit for your holiday party. I hope they give you some ideas and inspiration. Remember, you probably have the perfect piece already hanging in your closet. Rather than going out shopping for something new... use that money to give a gift. Frugal fashionistas totally rock this world. :)
1 - Decide on a Dress
Wearing a dress can cut out some of the stress that goes into putting together two separates. The dress is usually the key piece of the ensemble - everything else takes backstage. It is important to choose a dress that fits well and captures your personality.
A bold or striking color is perfect for winter parties and will really "make" your outfit. Accessories are not really needed when the color or design takes center stage. On the other hand, if you go for a more neutral color, you may want to use bold jewelry, a colorful scarf, or amazing shoes to enhance the ensemble.
Because it's a Christmas party (especially if it's formal) you can wear more lightweight or less "covered" pieces (ie. sleeveless designs). A pretty, ruffled little party dress is a fabulous choice. Of course, many of the dresses that are sold these days are very much on the short side, so if your dress is a little bit too "little" I recommend wear dark dress pants/jeans, leggings or tights underneath. Too much bare leg *does* look a bit strange in the middle of winter.
Of course, there are also plenty of long-sleeved options as well... just make sure that whatever you choose really works for you. There's nothing worse than a dress that doesn't suit it's wearer (and there are a gazillion bad bridesmaid photos as proof ;). So... decide on a dress only if it's really you.
2 - Pull out the Pants
You can look every bit as dressy and stylish in a pair of beautiful, well-fitting pants as in a dress or skirt. And they are guaranteed to keep you super comfortable. Although pants usually are not the item that takes center stage in an outfit, they can serve as a great base to build your look around.
Of course, a great staple is some dark blue jeans... or black dress pants. These go with anything and are very classy (I recommend a boot cut style for a super flattering look).
But don't let yourself be limited! Pants in a fabulous color, cut or design can be absolutely amazing. Something metallic (silver-y or gold/bronze) is perfect for the holidays and provides some nice "sparkle" - just pair it with a simple, neutral top and a matching necklace.
I also recently stumbled across a look in a magazine that featured flared blue silk pants - it was almost like a 1940s or "pajama" look - with a sparkly top. It was absolutely adorable and - IMHO - it should be a yearly winter trend. Who's with me? ;)
3 - Try a Top
Go for fun details and unexpected touches! This year, it is all about ruching, ruffles, bows, draping, and pleats. Selecting a piece with some really interesting details allows you to cut back on accessories. When you've got ruching or fabric roses around a striking neckline, it's really best not to add a necklace to the equation.
Also, if you tend to get a bit chilly during these winter months, you may want to opt for a sweater as a top. These can be worn by themselves, or layered over camisoles, turtlenecks or other tops for an equally lovely look.
Lastly, never underestimate the power of a beautifully fitting knit-top or simple button-up. If the shape, color, and your outfit as a whole work - there's nothing else you really need.
4 - Select a Skirt
Skirts can be pretty interesting these days, featuring all sorts of fabulous colors, fabrics, prints and details. If you pick something unique enough that it can stand on it's own... let it do just that. The rest of your look should stay simple - a backdrop to the amazing design you are wearing.
A simple, neutral skirt can be just as stunning when the shape and fit are perfect for your look. I am a big fan of pencil skirts (although I have yet to find some that fit me right :P) - no skirt says "classic style piece" like them. (A pencil skirt if the LBD - Little Black Dress - of the skirt world. ;)
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Hmm... are you confused already? Or has this post given you some good ideas? Feel free to share your favorite pieces and looks for the holidays! :)

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