The Secret to Occasion Dressing

How to honor dress codes and still still stand out

I recently had a moment of self-amazement when I realized I’m at a point in my life and a place with my style where I can be invited to any given event on any given day and have something to wear. And even if I have to cobble an outfit together, it’ll still be appropriate and look pretty good.

A few weeks ago, my boyrfriend started a new job and asked me to be his +1 to the company holiday party. I knew I wouldn’t be able to get details out of him right away (he just doesn't pay much attention to that sort of thing), so I immediately started planning outfits in varying degrees of fanciness. Two days before the event, he reveals that it was cocktail attire at a fancy Italian restaurant. Boys! But I didn’t sweat it because I was prepared.

The me of a few years ago would have totally spun out as soon as I got the invited, looking through every page of the Urban Outfitters sale section, Forever 21 and H&M, desperately looking for something amazing to wear specifically for this one event, but ending up with something that was just OK that I'd never wear again.

This whole scenario reminded me of an episode of The Carrie Diaries, the Sex and the City prequel series that follows a young Carrie Bradshaw in high school. Has anyone other than me seen this show? Also, season 1 is amazing but I cannot stomach season 2.

ANYWAY, there’s an episode where Carrie’s very rich boyfriend invites her to this fancy soiree his mom throws every year and her only instructions were to “wear blue.” When she runs into her boss on her lunch break while trying to find something to wear, they have the following exchange:

Carrie: I've never been to a party like this. Kinda nervous. I'm supposed to wear blue.

Barbara: Sapphire. This is navy blue.

Carrie: Is there a difference?

Barbara: In Kick Silver’s world, there is. Let me help you. It’s called the jewel party. It’s one of the most talked about events of the social season. Each woman is assigned a color. Either ruby, emerald or sapphire, and Kick wears white and covers herself in rubies, emeralds and sapphires.

Carrie: Wow. George didn’t tell me. He just said “blue.”

Barbara: Well, that’s my George. Like most men, not one to focus on the fine points.

It gets worse. And way more specifically and ridiculously relatable. When George comes to pick Carrie up, we learn of another dress code wrinkle. George arrives in a tuxedo and Baraba and Carrie immediately freak out and ask him why he’s in a tux. “Because it’s formal...did I not say that?” And Carrie’s in a cocktail dress!

Carrie: I can’t go like this.

George: Why? You look beautiful.

Carrie: Because I know hot these things work. If I show up in this dress, I will forever be known as the girl who came to Kick Silver’s soiree in a knee-length dress.

Carrie does a genius creative sitcom thing at the very last minute and fashioned some old tutus together to create a maxi skirt over her dress and looks absolutely fabulous, of course.

I ended up loving my outfit for the holiday party and I can’t wait for an occasion to wear it again. I went with the two-tone printed Rachel Roy wrap dress featured in my high school reunion post with a Miss Selfridge faux leather jacket and a pair of Chinese Laundry red ruffle heels I bought on Amazon for $20. A shining example of high-low dressing!

Which brings me to my approach to occasion dressing: Be appropriate, yet unexpected. If you can, find out what the dress code is. Is it black tie optionial? White tie? Formal? Cocktail? If you’re not super familiar with the ins and outs of that dress code, do some research! What dress lengths are acceptable, how much sex appeal/room to show a lot of personality is there? Then, have at least one outfit detail that’s a little unexpected. It can be as subtle as wearing a formal dress and wearing natural makeup and messy hair.

Do something contrary if it's something you'll feel confident and sexy in. If most people will be in dresses, maybe go for a jumpsuit or separates. Most people will also probably go for classic holiday looks like red, emerald green and lots of shimmer. Go for whit or navy!

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For my outfit, I went with a pretty traditional dress silhouette and the red ruffle heels are very holiday party, but the print and the color-blocking of my dress made it unique. I also paired it with a cropped biker jacket rather than a wool coat and took a white early 2000s mall baguette bag I found at Goodwill. And with minimal jewelry (simple stud earrings, mini gold Casio watch) hair and makeup, I thought the look was very elegant and cool. It's all about striking a balance.

Of course, I always seem to forget how atrociously underdressed Seattle as a whole is. There were people in khakis and a sweater over button-up shirts and girls who wore backpacks and flats. But I didn’t feel uncomfortable and overdressed for one second because I knew that I was dressed appropriately for the occasion and looked great. If anything, I hope my seemingly effortless essence made the khaki-sweater people feel underdressed.

Diana Le

Diana Le

Diana is the co-creator and Editor-in-Chief of Oatmeal Cardigan.