How to Dress for a Cool Friend’s Wedding

When the black dress that you’ve already worn to ten other weddings will not do


This is the type of wedding where you already know the band is going to be awesome. The deejay following the band, once it gets late, will play a satisfying array of bad pop music for the sake of nostalgia and irony. She’ll play obscure tracks, too, and they’ll come on at just the right moments — like when everyone needs a break from dancing but wants to keep the buzz while they take a breather. Those lucky few with their phones alive or nearby will try to capture the song on Shazaam with great discretion. The rest of us will try to fake it and sing along.

There will be no mason jars. The floral arrangements will be inspired. They’ll probably do something creative for dessert, like doughnuts instead of cake. Their friends will give the best speeches. People will actually listen to the speeches. Ugh.

This couple is cool.

Which means that boring dress you’ve already worn to 100 different weddings — yes, that one — won’t cut it. It’s already been in 2 of your profile pictures. The dry cleaners are sick of steaming it. So what the hell do you wear?

I asked Leandra. I instantly regretted asking Leandra because our aesthetics are so different and she’s always trying to chase me out of my comfort zone and make me middle-part my hair. But sometimes a girl has got to take a risk, especially if Leandra threatens to fire her for the thousandth time.

Besides…she sort of knows what she’s doing, right?

First, the casual-optional option


Tibi burgundy dress, VEDA x Man Repeller military jacket, Jonathan Adler vase as purse, Ralph Lauren shoes, Monica Sordo and Lulu Frost necklaces

Leandra’s addition of the utility jacket was kind of genius (don’t tell her I said that) because it’s an easy-to-carry outfit neutralizer if you arrive and realize you misread the dress-code. Ohh, you said *not* fancy.

And if the situation’s reversed (Ohh, you said 100% *not* casual), you take it off and hide it on top of a candle!

Next, the conversation starter

Tome skirt and knit top (other metallic options here and here), Stella McCartney shoes (here's another green option), Smythe coat.

Tome skirt and knit top (other metallic options here and here), Stella McCartney shoes (another option here), Smythe coat

Shy is not the right word, but I can be a little, “I don’t want to talk to you.” Leandra knows that, so she gave me conversation starters.

“Cool thing on your head, what is that?” is easily answered with, “My festivities crown!”

“Hey, do you know I can see your bra?” is easily followed up with, “Let’s dance!”

And so forth.

Finally, balls to (the window) to the walls


Tibi pink sequin dress, Tibi sandals, Garrett Leight sunglasses, Junya Watanabe Comme Des Garçons black jacket

If teens do it for the Vine, then we can do it for the wedding hashtag. Ruffles, sequins, sideboob and sunglasses — anything you’d normally hide from, try it, because nothing is off-limits so long as you’re not wearing the same outfit as the bride.

As long as you’ve got that covered, you’re cool.

Photographed by Krista Anna Lewis


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