What to Wear to Your High School Reunion

I’m pretty sure I want to go to my high school reunion. I think it’s most likely true that there are two types of people that go to their high school reunion: those that peaked in high school (yikes) and those that survived, are thriving and desperately have something to prove. As you may have guessed, I fall into the latter category. Although I’m a little bit in denial because I don’t want to admit to caring, let alone to desperation.

But who cares if I care, right? Everyone needs a good redemption story. You know the one. Of those who were massively overlooked in high school and then in adulthood came out of nowhere and took the throne.

I’ve definitely spent a lot of time thinking about what I would wear. I graduated high school in 2010, so my high school reunion is still about three years away. Yes, it’s completely neurotic of me to be thinking about what I’ll be wearing this far in advance, but high school reunions call for some serious stunting. And I think I’ve found the perfect look.

Miss Selfridge Retail Ltd (US)

Have you seen that weird indie romantic drama One Day with Anne Hathaway and Jim Sturgess? They never quite happened right after college and run into each other years later at mutual friend’s wedding. Jim Sturgess is talking to someone they went to school with and is like, “Omg is that [Anne Hathaway’s character]?”(sorry, the film is mostly forgettable except for this dress. And the ending, omg!) as his mouth drops and she walks in wearing a beautiful blue cheongsam dress. I’ve long fantasized about inciting a similar moment from unconquered crushes (think Adele’s “When We Were Young”), which is totally inappropriate now that I'm in a relationship, of course. But I've also been thinking about the dress Anne Hathaway wore.


Buuut because I’m asian, I’m worried wearing a cheongsam dress might be too Benihana. So when I saw this Rachel Roy dress I thought it was the perfect cool, modern interpretation of it.


Even with the mixed colors and prints, I feel like the dress lends itself to being paired with so many exciting shoe options:

The pink, because blue and pink — duh. I've also been into a bit of Gigi Hadid matchy matchy color blocking, which the navy heels would be great for.

I considered leopard print, but though nah, go for the snake print! And the red pumps are just truly evil.

To pull all this together? A white biker jacket, what else?


Urban Outfitters Patent Leather Moto Jacket

Isn't it so Sloane from Ferris Bueller's Day Off?

This outfit is totally my modus operandi: extra, yet elegant.

If you, like me, are over thinking or did overthink your high school reunion revenge body look, I’d love to know what you’re planning on wearing/wore!


Diana Le

Diana Le

Diana is the co-creator and Editor-in-Chief of Oatmeal Cardigan. She works as a copywriter by day and moonlights as a texting guru by night.