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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  • Stephanie

    Nice dress <3 | Join WORLDWIDE giveaway

  • That pink dress and black jacket …! The only problem is you’ll get a potential husbands infection if you dress to a wedding like this. Not sure I wouldn’t pop the question if I saw you standing there like that … 🙂 (an Oldie Joke on Tuesday, how bad’s that?)

    • Amelia Diamond

      hahaha Alcessa!

  • Natty

    challenge accepted

  • LP

    Wear a riding outfit. You’ll look/feel like you, and when someone asks you if you like horses you can be like F***K yeah. Nothing feels cooler than just doing you.

    • Amelia Diamond

      LP. You get me.

  • Kaleigh Fasanella

    the hair! the side boob! the rad AF jackets — can I be you plz? xo

    • Allie Fasanella

      cute comment

      • Amelia Diamond


        • Allie Fasanella

          “sisters? hallie, we’re like twins!”

    • Amelia Diamond

      we are each other!

  • Allie Fasanella

    you are the essence of cool AD. I need everything in this story

    • Amelia Diamond

      candy for you!

  • Abigail

    the utility jacket doubles as a good looking way to hold your things if you decide to bring a candlestick instead of a purse!!!!!

    • Amelia Diamond

      this is very true!

  • Leandra Medine

    i did a really good job
    i feel good about how you look
    especially in tome

    • Amelia Diamond

      OH K.

  • Jacqueline Ho

    AHH Amelia you got to wear the Tibi dress from the runway you loved so much. Might I add it looks AMAZING on you <3 and the styling by Leandra is pretty on point!

  • Kate

    amelia you look amaaaaazing! pink dress + side boob W0W

    • Amelia Diamond

      side boob is so dangerous!

  • Greer Clarke

    I have been obsessed with that gorgeous black piece o black puff since Leandra wore it as herself interviewing herself circa 2012

    • Amelia Diamond

      this made me lol

      • Greer Clarke

        Pls don’t hide that one on top of a candle

    • Lua Jane

      Me too. It’s like my regular obsession motorcycle jacket only bazillion of times cooler.

  • Tess

    tbh it took me an embarrassingly long time to find where your arms are in the CDG jacket..

  • Just about everything from tibi is a life-saver for cool weddings!!

  • Malu

    These are all really cool pieces. You would almost never think to wear them to a wedding because there is this standard of dress code and many people would probably look at you crazy to dare to come dressed like it. I love them all. I think it is the ultimate way to look cool and chic at a wedding and who wouldn’t want to look like that?! great post

  • It was the correct decision to start with that look there.

  • M-Th G

    She beautiful.

  • I now need a cool couple friend. And then I need them to get married.

  • John Mattinen

    FUGLY and UGLY MEANS…allbad photoes here

    unions Ok but Global mandatory family planning, no one ges married unless 2 kids or less;

    so it doesn’t matter what brand you wear just less reproduction please

    all fashions ends in landfill

  • ThisPersonSleeps

    I love dress No. 3. Yall are so cute. I have a wedding this weekend and the ONLY thing I have to wear is a black dress. Oh wells..

  • these outfits are killer!! have to say my favourite is #2 but honestly love them all!!
    anna //

  • YoBabyWazUp?

    hmm. This girl is beauTiful:) Buut the side boob dress looks super uncomfortable. A dress you wish you hadn’t worn kinda dress. What about a suit?