Ahhhhhhhhhh the office holiday party.  It [is] the best of times, it [is] the worst of times.  You finally get Gina from bookkeeping to loosen up a little, but Frank from sales gets quickly overserved and won’t stop telling you about his five-year-old’s likely NFL prospects.  The kid could catch a ball at age four.  We get it.  He’s a prodigy.  Definitely gonna be a first round draft pick. #SomebodySaveMe

Aside from navigating super awkward coworkers at the event itself, the whole “what do I wear to my office holiday party” thing is about as debilitating a challenge as they come.  It isn’t easy to tow the line between in-the-presence-of-my-boss appropriate and suitably (pun intended?) festive for the occasion.  And, as always, no two offices or office holiday parties are the same, so what your BFF has picked out for the swanky upscale party at 1 OAK that calls for cocktail attire is going to be wildly out of place at the casual holiday lunch party held at your office.

To help you navigate, I’ve broken down work holiday parties into the following three categories: casual, business formal and cocktail.  I’ve included my favorite looks for the occasions which you may remember from my ongoing #30DRESSESin30DAYS series, as well as lots of additional ideas in each category for those of you on the hunt for the right look.

CASUAL OFFICE HOLIDAY PARTY

PLAID DRESS |  LEOPARD HEELS  |  BELT (also HERE)  |  TOTE BAG  |  LIP

Additional casual office holiday party favorites:

BUSINESS FORMAL OFFICE HOLIDAY PARTY

DRESS (50% off!!) |  BAG  |  SHOES (love affordable options HERE)  |  EARRINGS (obsessed with these!)

Additional business formal office holiday party favorites:

OFFICE HOLIDAY COCKTAIL PARTY

DRESS (30% off with code CM2016!! love the a-line version HERE and blouse version HERE)  |  PUMPS  |  BAG  |  EARRINGS  |  BRACELET  |  LIP

Additional favorites for an office holiday cocktail party: