Roaring Into the 20s


2020, new decade, new year's eve, roaring 20s

Happy (almost) New Year! It’s hard to believe we’re already about to start another year AND another decade. How does New Year’s always sneak up on me?! I haven’t spent any time reflecting yet or pondering what goals I want to set for 2020, but I have, of course, had this amazing flapper outfit planned for quite some time now… How could I not rock a flapper outfit on NYE when we’re entering the Roaring 20s again? You’ve probably caught on by now that I have a slight obsession with the fashion of that era. 2020, here we come!

Roaring 20s, flapper style, flapper girl outfit, flapper dress

While I’ve dressed as a flapper girl in the past, I feel like I really upped my game this time. Of course, the burgundy fringe dress from White House Black Market is the star of the show, but I accessorized it with gold heels (I can barely walk in them, let alone dance the Charleston), two pearl necklaces, the gloves from my Audrey Hepburn Halloween costume, vintage-style makeup, and a killer hair-do.

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If you’re attending any 20s themed NYE parties this year (I know they’re very popular!) you can easily recreate this look by grabbing a shift dress from your closet. Flappers always wore dresses with either a drop-waist style or a shift shape, so basically, dresses with no shape at all. Fringe and beads are always welcome too! In terms of accessories, the gloves aren’t necessary, as you probably won’t have something similar already in your closet. But pearls are essential, whether that be pearl bracelets or lots of long, layered pearl necklaces. To stay warm, layer on a feather boa or any silky/chiffon scarf over your shoulders.

For the hair-do, it’s actually way easier than it looks! And it didn’t even take that long. Start with your hair down and put a sparkly headband across your forehead. Chunk by chunk, start tucking strands of hair around the headband and pull them through. Do this all the way around your head, and then tie the ends into a bun. I did a side bun, but you could do it on the back of your head as well. Make sure to loosen it up by pulling gently on the strands that you wrapped through the band.

For makeup, flappers often wore dark eye shadow, either black or eyeshadow that matched the color of their dress. They also put distinct darker shadow in the creases and smeared it upwards (I put a burgundy shade on my lids and a sparkly black in the creases). They usually wore a dark lip with an emphasized bow (the little dip in the center of your top lip), which I accomplished using lip liner and a matching liquid lipstick. But if that’s too much for you, a simple smoky eye and nude lip gloss would look just as good!

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On a more serious note than the fun fashion of these photos, I usually really struggle with this time of year. The holidays are over, everyone has to return home/to their jobs/to school/to reality, and the end of the year is a constant reminder of all the goals I didn’t accomplish over the past 12 months. It sounds pretty negative, and it is. But I know I can’t be the only person feeling down right now.

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In an effort to combat these dreary emotions, I plan on spending my New Year’s Eve making a list of all the things I DID accomplish in 2019. It’s so easy to get caught up in your failures and what didn’t get done, but we often don’t give ourselves enough credit. Sure, I still haven’t monetized my blog or fully fixed my website after last winter’s snafu, but 2019 was a great year for me! I should celebrate it and be thankful for all of its gifts, instead of wallowing in disappointment. While I’m at it, I might as well round up a list of accomplishments from the decade! Go ahead, pop a bottle of champagne (more like, Martinelli’s) and celebrate YOU this New Year’s Eve.

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My biggest accomplishment this past year was walking the Camino de Santiago, but I also started my first real job as a research assistant and was promoted, I had a piece of writing published in a book of short stories, and I crossed off a total of 8 items from my bucket list (!).

In the coming year, I’m looking forward to…

  • Visiting my friend at her college sometime in February/March.
  • Getting an internship this summer. (For what? Where? How? I don’t know!)
  • Studying abroad in the fall in either Scotland, Italy, or Wales.
  • Turning 21 so I can wear this outfit to one of the super-trendy speakeasies popping up everywhere.
  • Also wearing this outfit to a Roaring 20s themed NYE party next year that I can’t get into this year because I’m not 21 yet…
  • Crossing off more bucket list items!

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What are you looking forward to in 2020? And even more importantly, what are you proud of accomplishing in 2019?! I’d love to chat in the comments, as well as hear your thoughts on the Roaring 20s being BACK! I’m convinced that if I just start wearing my hair like this regularly and lots of shift dresses, then the flapper style will actually come back. It won’t just be a costume. Thoughts?

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Have a wonderful Monday and a safe and happy New Year’s. See you in 2020!


Miles of smiles,



Red Fringe Dress: White House Black Market, $100 // Gold Shoes: Vintage from my grandma // Pearl Ring Bracelet: Amazon // Headband: Charming Charlie // Long Pearl Necklace: Charming Charlie

8 comments on “Roaring Into the 20s”

  1. You are so dang cute! Love the outfit. My granddad and aunt used to dance the Charleston it was so fun to watch them. You brought back some good memories! Love ya. Happy New Year! I hope you love your 20’s decade and all the adventures it will bring. So much to look forward to! Hard to believe it’s my 60’s decade but looking forward to the adventure. Love you. Aunt Jo

    1. Aw, that’s so cool!! I would love to learn the dance sometime. Thanks Aunt Jo and happy 2020. 🙂 Surely there is a lot to be excited for this decade and I can’t wait!

    1. Such a great word! Thanks for stopping by, and I hope you had a wonderful New Year’s Eve/Day!

  2. OMG, Grace, you are absolutely stunning! It looks like you stepped right out of a Fitzgerald novel! I love this dress and all the perfect little styling details you incorporated. And I love your attitude about the past year. I think so many of us do feel like we didn’t get enough done before the calendar flipped, but the new year is such an arbitrary deadline to impose on ourselves. You absolutely have the right idea to focus on the good and focus forward! Great post! Wishing you all the best in the 20’s!


    1. Thank you so much Shelbee for such a sweet comment! I hope you have a wonderful start of the year and decade as well. 🙂 This photoshoot is definitely one of my favorites of all time!

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