What to Wear to Your Next Casual Holiday Party

Contributor: JoJami Tyler

I have a confession to make. I was TOTALLY STUMPED this weekend… I had a daytime, holiday party to go to and boy, did I have to work hard to find just the right thing to wear…

It seems that every time the weather changes or I have an event to go to are the times that I struggle with what to wear.
This party I was invited to  was a  cookie exchange party with a twist. You had to bring your cookie dough and bake cookies at the party, while enjoying martinis! Fun concept, but hard to imagine what to wear…. It seemed on the one hand, I should dress casual for the cooking part, while drinking cocktails with the girls, I wanted to look chic, but not too dressy.

But wait, there was one more thing… My girlfriend who was also going to the party, called me a few days before, to ask me what I was going wear and I told her DEFINITELY NOT JEANS, but probably a skirt of some kind.

Well, one of my rules to myself is, when I tell someone what I’m wearing, I better wear it!!!  So of course it was a 1/2 hour before the party, I was in the closet and the clothes were flying all over the place, and all the skirts just seemed too dressy, it was a really cold day and I wanted to be comfortable! OH, how I wished I could wear my jeans, but my friend was probably already on her way, and I could  call her to tell her that I had changed my mind. (Ends up that NO ONE wore jeans, so it was a good thing I didn’t!)

Anyway…. I floundered  for a while, then did find a casual dress to wear. I ended up feeling comfortable and that I dressed perfectly appropriate for the party!

So here is a Glam Plan for how to look comfortable, but chic for an afternoon holiday party!

1. Plan ahead! Don’t just pick out what you want to wear, try it on and make sure it looks good and you have all the accessories you need.
2. Start your outfit with what  shoes you want to wear. If you know you are going to be doing a lot of standing at the party, think twice about those killer heels. Boots are great for this time of year, low or high, you can still pair them with a skirt, pants or leggings
3.  Fabrics should be cozy and comfortable (colorful cashmere comes to mind!)
4.  Invest in a beautiful top or jacket. If you’re out shopping for an outfit, so as not to go into overload, start with one piece that stands out to you. It could be a pretty jacket, sweater or again, you can start in the shoe department.
5. Beware of going for the same look you always wear. Search catalogs and magazines first, to get a fresh idea of how to pair 2 pretty colors or a  new type of look.  (Did any of you happen to see Nicole Kidman on Oprah the other day…. I LOVED her outfit!) Her purple suede jacket with a tank top – the exact color as her hair, pencil jeans and matching heels!! Perfection and not too hard to duplicate!)

nicole-good

Just jeans, heels and a jacket – but it’s perfect!

Here is my outfit, that I was so comfortable in. I admit, grey is not my best color, but I tried to liven it up with the scarf, and overall, I think it was a good casual look for this type of party. (In case you are wondering…yes, that is a paper plate I am “modeling”) Also, I have a new hair do AGAIN!!!



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  1. I’m a 45 yr old. going to a holiday party at a Cleveland Nightclub. My dress is gold on top black just above the knee skirt. I only have black open toe shoes. Is that ok this time of year? or do I need closed toe heel with black tights.

    • Hi Barb, The black tights should look fine with the open toe shoe…however you might also want to try a sheer black hose and see which one you like the best! Feel free to send us a photo and help you decide! Have fun, you dress sounds wonderful!!!