5 Holiday Occasions + What to Wear for Each

With holiday parties, dinners and Christmas all coming in full force over the next few weeks I’m rounding up outfit ideas for each of these occasions …. and geographical locations. I know not every one of you reside in a cold weather destination so I’ve pulled together a few styling tips and tricks to make sure you’re looking just fabulous no matter where you are and what the occasion calls for. 

The holiday Gala

Gala season and the holidays have started going hand in hand these past few years. I find my calendar just as packed with charity gala invites as I do with holiday party invites. No complaints here, I’d much rather do good any day of the year and if I get to do it in a black tie dress than so be it!

I broke out this Bronx and Blanco number that I wore to a friends wedding in October for a recent charity event at The Whitney museum and it was perfect. Paired with statement earrings and a black strappy heel, the look was just right for the occasion.  Or go with this dreamy velvet number that I was crushing on pretty hard but opted for the longer option!

The Holiday office party

Let’s be honest, you want to go to the work party to show face, have a few drinks with colleagues and then get on out of there to meet up with your friends, your SO or to go home. You spend 90% of your time with these people!

So go with an outfit that you feel is you. No need to go over the top. I recommend a great statement blazer (similar here and here) and beautiful pair of heels paired with jeans if you’re in a more creative environment.

Not so much in a creative environment (i.e. you’re slaving away on excel sheets and crunching numbers)?

Not everyone works in a creative space or even a casual work environment so this holiday I’m showing you a few options that fit the bill for even the most corporate of work environments like this Trina Turk dress. I wore it recently for the event I hosted at the Trina Turk store in NYC – note I did tailor it a bit to my 5’5” frame.

The dress is simply glamourous with a very retro take on a dress that can be worn to a finance corporate office holiday party or when hemmed (a la how I wore it) to a festive party with friends!

Styling tip. If you don’t want to hem it permanently use hem tape to make it shorter and then easily bring it back down to a longer length. Also go down a size, it runs big but again, I am totally smitten with it! Paired again with THESE DROP DEAD GORGEOUS HEELS.

Dancing around the Christmas tree with your girlfriends

Nothing says Happy Holidays like a festive dinner and drinks with your crew, am I right? Sometimes you go all out and sometimes you just come from work so wear something that can translate across all. I love this little dress paired with booties but you can easily do a great heel to dress it up more. This Tracy Reese sold out but I found a similar one here.

A festive dressy Christmas!

While my family is often a bit more on the casual side, some of you get dressed up for Christmas dinner, which to be honest I’m a little bit jealous of! I love to dress up, give me any reason to put on a fun outfit and heels! This sequin number is festive without being too in your face over the top. The perfect holiday dress. This one is sold out but I found a similar one!

Going casual this Christmas?

If you’re anything like me I despise being cold. I actually legitimately hate freezing (unless I’m on a ski slope then it’s another conversation!) But come Christmas day my family and I are casual. It’s home, there is a fireplace, dogs and lots of time in the kitchen cooking up more food than our little family can consume. So how can I be bothered to put on a dressy outfit?!

You can find me wrapped up in a cozy long cashmere sweater with my favorite pair of just-worn-in-right jeans or a big chunky sweater and of course a pair of my favorite jeans just in another wash or these cropped pants. Just thinking about it gets me excited for the big day!

AND last but not least, going somewhere warm and sunny?!

Make sure to pack a long maxi dress that can be paired with silk slides or a great heel. The look is ideal for those upcoming Hawaiian escapes or trips down to the Caribbean that I know so many of you are taking!

Shop the post and similar pieces to these looks:


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