What to Wear to A Casual Holiday Office Party

During his career, my husband has worked for several employers. I used to hate going to their holiday office parties because I never knew what to wear. They’re usually held at the end of a workday, so everyone was casually dressed, or so I thought.

At one party, I showed up wearing a simple outfit and found the female employees had brought long, formal, sparkly gowns to change into before the party. Gowns! I felt very under-dressed.

Another year I dressed in a little sparkle only to find the other women just stayed in their work clothes. Being dressed appropriately for these parties always felt like a moving target because I didn’t know the employee’s and have no idea what they will wear.

I finally decided to dress the way I would feel comfortable, no matter what anyone else wore.

Trends can be quicksand for the woman over 50 but touches of it make you look modern and current. Gray is on trend this season and I just happen to already own and love it. Softer and less formal than black, it’s perfect for this occasion.

The party will require lots of standing so my shoes have to be comfortable. I want to look great, but if my feet hurt, it’ll show on my face. Not worth it! I’ve worn these booties for years so I know they’re super comfortable.

A Casua Holiday Office Party: Hitting Your Style sweet Spot
Black suede and gray tweed “spats”

There’s just a touch of glimmer, with the sequins on my top.

A Casual Holiday Office Party: Hitting Your DStyle Sweet Spot
Black velvet, Fendi bag with a crystal medallion and tassel. I’ve had this handbag over 30 years.

I’ll be shaking hands and nibbling appetizers at this holiday office party so I carry an evening bag with a shoulder strap.

A Casual Holiday Office Party: Hitting my Style Sweet Spot
I feel blessed to have some of my Grandmother’s jewelry. These are her Art Deco earrings from the 1930’s.

With the sequins on the top and rhinestone earrings, a necklace would be overkill. For me.

A Casual Holiday Office Party: Hitting My Style Sweet Spot

No matter what other people are wearing, I feel appropriate and confident.

I invest in my clothes and wear them for many, many years. Accessories almost never get edited out of my wardrobe. This is investment dressing and my cost-per-wear on these items is pennies per wear.

What do you wear to a casual office party?



  1. Jennifer- you look fabulous in that picture! I want those earrings!

    1. Thanks so much Jess!!

  2. I can’t tell you how many times I had to change in a bathroom at the end of the work day. As CEO, sequins at work wouldn’t work, but take off the blouse and stick a sequin shell underneath, and voila! I was ready. You look smashing!!!

    1. Thanks Wendy. It is little changes like the sequin shell, that make all the difference.

  3. Perfect. You look gorgeous. I love the shoes. I am also fortunate and have many of my Mother’s earrings and handbags to just add a bit of class.

    1. They really do! You are lucky! None of my mother or grandmother’s handbags survived to be passed down. I bet they’re very special!!

    1. ❤️❤️❤️Contessa!

    1. Thanks Patti! I feel so blessed to
      have her earrings.

  4. If you have doubts about what to wear to an event, say it’s at a swanky hotel this year instead of the office conference room, you can always bug Hubs to ask his female co-workers.
    My husband is totally clueless about what people are going to wear and I only had one dressing mis-match like that before I kept after him to ask someone. It turns out that the women he worked with were more than happy to oblige, in fact they had been mentioning it to him, but he hadn’t relayed the message to me.

    1. My husband was totally clueless too. I’m sure there was some direction he could have given me. It’s just outside his “give a damn” zone. He honestly couldn’t care less. I always look “fine” to him 🙂

  5. I love how the sequins and earring bring the focus to your face.

    Great chic outfit.

    I also have been told it is business casual for a Christmas party we are attending. Honestly 90% of the reason I even go to the Christmas party is to dress up. (It’s for business associates of my husband.)

    I’ll be overdressed and stand out, but I don’t mind at all. I’d rather be looked over than overlooked.


    1. I’d much rather be over dressed than underdressed!

  6. Perfect combo, Jennifer. A little sparkle says Holiday! I always carry a shoulder bag if I need a free hand, too. Actually, most of my bags are small shoulder bags. I hate purses and think of them as a necessary evil.

    1. They are a necessary evil. But I often wonder how men manage without one. They’re so convenient to carry our “stuff”!

  7. Jennifer, this is my idea of a perfect holiday office party attire. And I love how you reminded us that when we dress how WE feel comfortable then all will be well. Walking into a room with confidence makes all the difference in the world.
    As for my husbands office party, well, he got so tired of trying to please everyone and mix and mingle with spouses that we have a fabulous lunch catered at the office and give the wives a gift card to for a day at a day spa. I’m totally happy with this.

    1. Feeling confident makes all the difference in the world. I’d be thrilled with a gift card to the spa! What a great idea!

  8. You look perfect for any occasion Jennifer!! Just the right amount of sparkle and glam!

    The Arts by Karena
    India Hicks Holiday Collection

  9. You look stunning! Love your grandmother’s earrings…

  10. I love the outfit. Grey looks great on you but not so much on me. I agree about trends. The other thing is that every time I see leopard I think “age”. So that trend is one that I’ve decided isn’t for me, either. Although I have one piece that I wish I could fit into for no other reason than it doesn’t fit now. I bought some fun things in Sept that I wore in Santa Fe and will continue to wear this winter. Style is fun, but having your own style is most fun!

    1. Yes! Having your own style is the very best!

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