Holiday Party Lookbook

Exciting news #bossyones! Over the next three weeks, The Bossy One will be all about how to navigate the holiday season at work. In this three-part series, we'll explore holiday style, gift giving, networking and more. So put on your party dress and get ready for The Bossy One's ultimate Holiday Guide!

* * *

This week is all about what to wear to a holiday office party. Office parties come in all shapes and sizes and picking the perfect outfit can be tricky. 

When you're getting ready for an office party, make sure to consider the dress code. Holiday office parties can range from black tie to super casual, so you'll want to scope out the dress code in advance. When in doubt, it's best to emphasize "office" over "party" and keep your hemlines, necklines and conga lines decent.

Business Casual

Skirt: Zara (find a similar one here), Sweater: Forever 21, Watch: Fossil

This first look is a great option for a business casual office party. Pair a pleated midi skirt with a knit top for an easy, elegant look. Pleated skirts are a nice change from a typical pencil skirt silhouette and they are surprisingly easy to style. Midi skirts are also good investment pieces, since they transition well from work wear to casual wear. 

Add a little fun to this look with black lace-up pumps. Lace-up pumps pair nicely with midi skirts because the length lets you show off your shoes. Finish off your outfit with professional accessories like an elegant watch and statement necklace. 

If you work in a more formal office, add a collared shirt underneath the sweater or throw on a cropped blazer.

Business Formal

 Pants: Club Monaco (find a similar pair here), Top: Forever 21, Earrings: H&M, Shoes: Aldo

The second look is a great option if you're heading straight to a party after work or if the dress code is business formal.  Since you can easily wear this outfit to the office during the day, you won't have to worry about changing.

Pair a structured work pant with a textured blouse, tassel earrings and strappy heels. The key to a successful tone-on-tone outfit is to mix a variety of fabrics and textures. Get creative - think silk, metallic, patent, matte, embroidery, fringe, etc. If you feel like adding a pop of colour, try a bold red or dark plum lip. 

If your office has a strict dress code, add a structured blazer or tuxedo jacket to this look. If tall heels aren't your jam, try a pair of patent leather loafers instead. 


Skirt: Honey (find a similar one here or here), Top: Club Monaco, Shoes: Ann Taylor

Evening office parties are a great excuse to get dressed up. I love a glossy, full midi skirt for fancier holiday parties. They feel so glamorous and old-Hollywood-y. When choosing a full midi skirt, look for a stiff fabric like taffeta, brocade, jacquard or polyester so that the skirt holds its shape and gives you that 1950s silhouette. 

Balance the fullness of the skirt with a slimmer top, like this striped sleeveless number with an embellished collar. This look would also be beautiful with a simple fitted black turtleneck. Finish off your outfit with a pair of nude pumps. Nude pumps are a great way to elongate the line of your leg if you feel like midi-length skirts are hard to pull off.

Keep in mind that evening office parties are still office parties. Be extra careful with cutouts, fit, hemlines and necklines. You want to find a (sometimes tricky) balance between evening wear and professionalism. 


Jeans: Gap, Sweater: Tommy Hilfiger, Watch: Tissot, Bangle: Coach, Shoes: Payless Shoe

If your office has an informal holiday party with a casual dress code - maybe a weekend luncheon or BBQ - this outfit is a great option. A nice pair of dark jeans are a staple piece that you can dress up or down depending on the occasion. It's safest to stay away from distressed, acid washed and light-coloured denim for work events. 

Pair dark jeans with a cozy, oversized sweater for a festive (and warm!) look. I can practically hear snowflakes falling when I look at this sweater. When you are going casual at work, it's best to keep your accessories sleek and professional.  I love the look of simple, polished accessories like a watch or bangle (or both) with casual wear. 

Finish it off with a pair of pointed-toe pumps or a high-heeled ankle boot. If you can't hack heels, opt for an elegant almond-toe ballet flat instead. 

* * *

I hope this post has you feeling festive! I would love to see your holiday party outfits in the comments below or on social media. Don't forget to click the "like" button if you enjoyed this post and follow me on on Facebook, Instagram and Pinterest.

Facebook/Instagram (@thebossyoneofficial) - Pinterest (The Bossy One)