What to Wear to the Wedding That Feels More Like a High School Reunion

Maggie Rizer and Karen Elson
Photographed by Ellen Von Unwerth, Vogue, June 1998

Congratulations! Your best friend is getting married to a man with a strong jaw and a full set of teeth. And no, we don’t mean your best friend who you’ve met in your new city or town, through work or through roommates. Instead, we are talking about your high school best friend, you know, the one who you skipped class with, hung out at the local pizza parlor with, and cruised around in a Jeep with throughout the winding, barren roads of your sleepy, one-gas-station town.

Now, maybe you left your former town and are successful with a studio apartment of your very own and a stellar doorman who presses the elevator buttons for you—or maybe you chose to stay close by, residing happily and cheerily with your husband, a tow-headed child, and a dog with three legs named “Tripod.” Either way, we bet you are doing fantastic things! Except, here comes the tricky part—you haven’t spoken to anyone from high school, except for your bride-to-be best friend, for years. That means, get ready to see the local folk for a mini Romy and Michele–style high school reunion, which includes the former sweetheart who took you to prom, the frenemy who once put peanut butter in your backpack, and a valedictorian who always needed to feel validated. Sounds fun? No—but it can be.

The key to making this an enjoyable and bearable time is to first take a cue from Teddy Roosevelt and “Speak softly and carry a big stick.” This means, there’s no need to talk a big game about how great you are—and nor should you dress that way. You are already satisfied with yourself—the last thing you need is a look-at-me outfit and a helmet-style blowout that might inspire a few drunken tangents about your accomplishments à la Charlize Theron in Young Adult.

“Remember, this isn’t your time to shine. It’s the bride’s. It’s not about having a boisterous ball gown with something to prove,” says Vogue.com Market Editor Chelsea Zalopany. “Instead, your behavior, as well as your clothing choices, should be elegant, memorable, polite, and a little demure.” To express those qualities sartorially, abide by the dress code but keep the overall look relaxed. A charming sundress with a floral pattern and a block heel is a stellar fit for something outdoors, while for a formal black-tie affair, you can opt for a organza gown with deep décolletage but a low kicky shoe. But remember, no matter what you choose to put on, make sure you are comfortable. If you are secure with what you are wearing—and especially with yourself—you’ll pass the occasion with flying colors.

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Mary Kate and Ashley Olsen

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Wedding Outfits

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Kate Moss and Johnny Depp

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Natalia Vodianova

Photographed by Mario Testino, Vogue, September 2006
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Chiwetel Ejiofor and Kate Moss

Photographed by Mario Testino, Vogue, December 2013
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Clueless

Clueless

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Kendall Jenner

Kendall Jenner

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Alyona Pivovarova Hana Soukupov Irina Kulikova Jessica Stam Sasha Pivovarova and Victoria Ionina

Alyona Pivovarova, Hana Soukupová, Irina Kulikova, Jessica Stam, Sasha Pivovarova, and Victoria Ionina

Photographed by Arthur Elgort, Vogue, June 2009
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Wedding Outfits

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Maggie Rizer and Karen Elson

Maggie Rizer and Karen Elson

Photographed by Ellen Von Unwerth, Vogue, June 1998
Wedding Outfits

Wedding Outfits

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