How to Wear the Same Dress to 5 Different Holiday Parties
12.19.17

I wouldn’t typically describe myself as antisocial, but I spent the months between summer’s end and November avoiding any sort of engagement that required me to A) participate in small talk, B) venture out of my comfort zone, C) dress up or D) all of the above. Now that it’s mid-December, however, as if by magic, I suddenly want to go to every random party on any given night of the week.

The eggnog’s been great and all, but my go-to jeans and white blouse got boring fast. When Amelia proposed I style one dress for five different parties, I took it as the opportune moment to ameliorate my own party style stump.

I accepted the challenge dutifully and chose this Haider Ackermann dress as my partner in crime.

For a Fancy Art Gala (That You May or May Not Have Been Invited To)

While I tend to be a more casual dresser, I do love a good opportunity to dress up, especially if it’s an occasion that allows me to wear something I normally wouldn’t. At a fancy art gala, for example, there’s a dress code, but it’s a creative-enough environment that you can wear a long silk black dress over a pant suit without feeling too fAsHuN. You know? I recommend following your local gallery on Twitter to catch wind of party-planning, then crash their next big fête. The ol’ “lost invitation” excuse works well at the door.

This suit is one of my best Zara purchases from a few years back. If I were shopping for a suit today, I’d probably go with either this Ganni one (full disclosure: I work there, but my love for this suit is real) or the Admise one made in cahoots with Monica Ainley and Camille Charriere.

I think this is also the only sort of cocktail or black-tie event where I’d feel confident enough to wear brogues. I can’t get enough of these Eytys lately, and I love that they still give me some height.

For a Snazzy Fête

I don’t own many “nice” dresses, and I never think it’s an issue until I have something special to attend and find myself in a panic searching for something to wear. This Haider Ackermann is my saving grace in these cases. It’s extremely versatile, plus it’s currently on sale. In the event that you’ve already worn your equivalent of this dress as-is before, may I suggest some sort of sheer underlay? It’s a great way to bring in some color and expand your shoe options beyond the expected. A bold shoe like these Manolo Blahniks would have felt too stark, too forced without something to tie it all together, while a black or neutral shoe would have felt too…meh.

For an After-Work Holiday Party

Topshop turtleneck — similar here, vintage belt — another here, Zara shoes — similar here

If you have to rush to your party from the office, I’m not sure it gets any easier than this outfit change. Take off the pants you wore to work, slip your dress over the turtleneck you’ve been wearing all day (wear a turtleneck all day!), add a belt and shoes, and ta-da! No one will ever know it took you less than five minutes to get ready. If you’re into red lipstick, now’s the time to bring out your brightest.

Also, I wish I would have worn these shoes instead.

For a Cozy New Year’s Eve, Preferably in the Snow

H&M sequin turtleneck –similar here under H&M sweater, Ganni boots

This is my ideal New Year’s outfit: something really comfortable but still festive and dressed-up. I got this big cozy sweater from H&M last week and I’ve been wearing it nonstop. The sequin turtleneck is also from H&M. Because I’m wishing for a snowy New Year’s Eve in, these Ganni hiking boots are perfect for that fantasy. Pro-tip: Give old boots new life by switching out laces.

For Any “It’s My Party and I’ll Wear Whatever I Want To!” Scenarios (Even If It’s Not Your Party)

Talk about no small talk: This shirt lets me wear my heart on my chest; it’s $100, and the money goes directly to Planned Parenthood.

By the fifth wear of this dress, meanwhile, my creativity started to wear thin, so I resorted to my favorite how-to-pack-light hack and turned it into a skirt. I twisted the sleeves into a bun and secured it with a hair-tie. And as far as hosting my own soirées goes, I find skirts to be way easier to move around in, plus then I don’t have to worry about any wardrobe malfunctions.

If you’re trying to stretch one dress five ways from now until New Year’s, show or tell me how you’ve been doing it down below.

Photos by Edith Young.

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