Watch the segment on the WGN-TV website
The holidays are here and so are the holiday events. They can range from an office party to a cocktail or just meeting friends for brunch. That’s why I wanted to do the segment, “one holiday dress, four ways to wear it.” You don’t have to buy something new for every occasion. With just a few tweaks and some thoughtful accessories, one dress is all you need this season!
This post will be updated with new photos links to the segment by Friday, December 5th.
**This post contains affiliate links and I will be compensated if you make a purchase after clicking on my links. Amazon prices are as of 12/1/25.
One Holiday Dress
So, how do you pick one holiday dress for four models? It takes some planning and forethought. Before I could even start to look, I had to select the models. It’s hard to pick something when you don’t know the body shape of each person. Once I had everyone on board, I knew the features that I knew would be flattering to everyone:
- Let’s start with color. I needed a holiday color that would work on everyone. A true red can work on almost every skin tone. This shade is perfect – it’s not “too blue” or “too orange”.
- A flattering neckline – one that isn’t too high like a turtleneck or too low plunging. The neckline on this dress is great for all face shapes.
- A style that would define the waist (this is good for all body types.) This dress has ruching across the middle, helping it define the waist and also offer “forgiveness”.
- A three-quarter length sleeve dress is also flattering. Showing part of your arm is always a slimming feature.
- Because of the different heights of the models, a knee-length is universally flattering for everyone.
Once I knew what I was looking for, I needed to find a dress that would be available in all sizes and (hopefully) still available when the segment airs so viewers can have access to the dress if they like it! So, finally, this dress from Amazon was the winner. I went with red for the models, but my dress is the same style, just in black. Best news? The price of this holiday dress is just $50.
Office Party
Model: Natalie
For an office party, you want to be festive, yet professional. That’s the beauty of this dress – it can work just as well for the office as it can a cocktail party. We added “festive” in Natalie’s outfit in her shoes – the plaid pumps. Festive, but perfectly appropriate for work. To make it a little dressier, we added sheer tights (sheer are much better than opaque for this look.). We finished off her outfit with classic accessories: chunky gold necklace and cuff, along with a red satchel.
Shop Natalie’s Look:
“Winter Wonderland” Glam
Model: LeeAnn
Fun is what LeeAnn’s outfit is all about! While this look may seem a little extreme, it does scream “holidays”! The white fur capelet, along with her silver accessories really does make it a “Winter Wonderland”. It reminds me of an outfit you would see in a Hallmark Christmas movie. Remember, you can always lessen the glam by swapping the silver shoes for a nude color and adding more classic jewelry. But we love this look just the way it is!
Shop LeeAnn’s look:
Vintage/Pearls
Model: Portia
If you are looking for a more traditional look, then Portia’s look is perfect for you. Very classy and elegant. We intentionally added a lot of pearls – to show that you can do as little or as much as you like. That’s why we added the pearl shoe clips. These are the perfect example of how to add bling when you need it and when to leave it out when you don’t. All these looks are intended to give you ideas on how to make them your own!
Shop Portia’s look:
Edgy Casual
Model: Rhonda
Rhonda’s outfit is perfect for those more casual events – maybe meeting friends for brunch or a dinner date. It has an edgier look to it, but the scarf and the red dress still make it festive. We added the fur bag for some extra fun, but you can swap that for something more traditional or go hands-free with a crossbody. You can even change the scarf for a different look. In fact, this outfit would also be perfect with a heart-themed scarf for Valentine’s Day!
Shop Rhonda’s look:
My Holiday Dress
I wanted my outfit to be similar and to showcase the dress in a different color. I also didn’t want to distract from the models, which would have happened if I wore the red dress. So I went in the opposite direction and added the red through my boots. My necklace is handmade by one of my best friends who has an Etsy shop. She made this specifically for me for the segment to give me my own “festiveness”, but she does have more on her Etsy page.
Shop My look:
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Here are two other blog posts that you might enjoy too:
What’s The Best Neckline for your Face Shape?
How to Get That Hallmark Christmas Movie Look