Keys: take a risk with something dramatic, try vintage, go for unexpected contrast, show a little skin (or maybe all of the above!)
Option 1. Go beyond the little black dress. I thought I might never have a place to wear the black beaded evening gown when I bought it at the Goodwill Outlet, but was too good to pass up at $10. However, no one can accuse you of dressing up too much on New Year's. At a charity thrift store, it's guilt-free to buy a dress that you may not wear for any other occasion. You'll have donated to a good cause and scored a great conversation piece when people accost you at the party for looking so incredibly amazing.
Option 2. Try something extra dramatic. I snapped up this fascinator hair clip from Goodwill because it was so beautiful. After doing a little research, I discovered they're easy to put in even for a hair klutz like me with just a plastic hair clip and two bobby pins. Add a hat, gloves, fur (real or faux), belt, over-the-top jewelry. If Kate Middleton, Her Royal Highness the Duchess of Cambridge, can wear feathers in her hair, so can you! By the way, the dress and hair clip in this photo were each $5, from the Salvage Store and Goodwill, respectively, both in Portland Oregon.
Option 3. Go for unexpected contrast. Not everyone will have occasion to wear a ballgown like the one in middle of the photo collage (a thrift-store wedding dress is a ballgown on New Year's Eve, right?) but an unexpected addition like a jean jacket can make any conventional party dress stand out. Now, not every contrast will work. Stay away from pairing anything with garbage bags. But classic materials like denim, leather, and metallics and natural elements like wood, shell, and bone will often look good in surprising combinations. If you're tentative, go with a contrasting jacket or shawl. You can always take it off if you just aren't feeling it when you get to your event.
Option 4. Try vintage. Vintage clothes often bring back memories of loved ones like my grandmother with her treasured mink stole. There's no time of year more appropriate than the holidays for that. You'll stand out for doing something different. And guaranteed no one else at the party will be wearing the same dress.
Option 5. Show a little skin. (That's a little skin, even if you're under the age of 30 - New Year's Eve is not a rock concert.) The key to pulling it off is to cover the rest of yourself with classic, non-revealing clothing items. The outfit below works because the top is veiled by the elegant shawl, and the dress pants are impeccably cut White House Black Market, a conservative, upscale brand. Pair with some elegant heels, you're in business. (For those of you who are shocked by the idea of wearing a bra top to a New Year's party, consider that this is a lot less revealing than a bikini at the beach. Besides, this bra is embroidered with beautiful red roses, so it's meant to be seen...by someone, anyway...)
Take photos beforehand. Sometimes a photo can be more helpful than a mirror in identifying awkward outfit spots.
Consult with a sensible but somewhat adventurous friend. If you don't already know someone like this, find one! In my opinion, everybody could benefit from this kind of friend.
Go for very conservative jewelry like plain pearls, a simple gold necklace, small stud earrings or a classic tennis bracelet. The easiest way to succeed with an extra-dramatic outfit is to tone down everything but the star of the show.
I think New Year's Eve is a little like Halloween: over-the-top is in-the-know. So push your style boundaries. Just budget extra time on the way to the drink table in case there's a crowd waiting to tell you how fabulous you look! Who knows, you might inspire a room full of people to step into unexplored style territory. Hope you have a wonderful New Year's Eve and a great 2019.
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