Stay Home Holiday Bucket List

November 17, 2020

Holiday Bucket List I wit & whimsy

With the 2020 pandemic still very much underway, this holiday season will no doubt be looking different and for many of us it means staying closer to home or finding inventive ways to celebrate with our loved ones. I have loved doing my Stay Home Summer Bucket List and Stay Home Fall Bucket List with you all as doing so helps challenge me to figure out loads of ways to make the most of this year’s seasons. So of course I had to do one for the holiday season, too! I hope you’ll join me in ticking through these items to have a meaningful but safe holiday season.

Holiday Bucket List I wit & whimsy

I am so happy to be partnering with Ann Taylor once again to bring you this bucket list! Their latest collection drops today and it is full of cozy pieces for fall and winter but also plenty of fun and festive and cozy and comfy looks that’ll get you excited to ring in the holiday season. I actually had trouble narrowing down which looks to style for this post – there’s that many good items for your holiday dressing this season. 

Holiday Bucket List I wit & whimsy

Holiday Bucket List I wit & whimsy

My first look is all about this star printed tulle skirt. I had so much fun wearing this whimsical skirt and I think it looks great with pumps but could also be beautiful with heeled booties and tights. You could wear it with a cropped cardigan, a slinky tank or like I did with a puff sleeved sweatshirt. (I get major Carrie Bradshaw vibes from the tulle!)

Holiday Bucket List I wit & whimsy

Holiday Bucket List I wit & whimsy

Holiday Bucket List I wit & whimsy

Holiday Bucket List I wit & whimsy

Holiday Bucket List I wit & whimsy

Holiday Bucket List I wit & whimsy

My second look I have to say is just so much fun. Doesn’t it make you smile given how much it screams “holidays!”?!  I truly love how this outfit came out and this skirt is such a fun moment that you could wear with ivory, black or red sweaters or tops or go monochrome like I did with this super soft, super plush mock neck sweater which I think is extra fun when you add a red shoe! This velvet skirt is so comfy (elastic waist – heyyy!) and the perfect green. The velvet makes it extra festive and I love that you just slip it on – no buttons or zipper required!

I know holiday dressing this year looks different with no parties to go to as we might once have but we can still dress up for the small and safe celebrations with families or a few friends and even more so I think this year we need excuses to get dressed up! (I miss getting dressy!)

I hope these two looks get you inspired to do so. (I just have to say – putting these outfits *instantly* put me in a better mood. I was kind of giggling as I reviewed the photos because I just had such a big smile in all the photos. Clothes really can affect your mood and I think we could all use a sartorial pick me up this year – at the very least!) I’ve included even more Ann Taylor finds I’m loving below, too to get you excited along with me.

Stay Home Holiday Bucket List:

  1. Leave an extra large tip for your favorite barista. Go ahead, make their day!
  2. Support three of your favorite local businesses by shopping their stores or their online shops. This year it is more important than ever.
  3. Give gift cards to your postman/postwoman & delivery workers. While they can’t accept cash they can get gift cards. Let them know you appreciate all their work (especially this year!)
  4. Bundle up and support a favorite restaurant by having outdoor cocktails. Hot toddy anyone?
  5. Send holiday cards! This is a favorite annual pastime of mine. I asked readers for recommendations of some small businesses to support via this one and want to recommend Dogwood Hill, Matt Carlin Designs, Quick Brown Fox Letterpress, Katharine Watson Design and Annie Montgomery Design. (Thank you to the w&w readers who recommended these small businesses!)
  6. Bake holiday cookies! Try and find a new favorite recipe you’ll want to make every year.
  7. Try making extra rich French-style hot chocolate. I recommend this recipe. Try adding some marshmallows, whipped cream or a bit of crushed candy cane!
  8. Donate to a holiday toy drive. Make a child’s Christmas brighter.
  9. Decorate your home! A reader told me she was making her space feel like a “Christmas Oasis” this year and I couldn’t love the idea of that more.
  10. Have a holiday movie marathon. Cue up your favorites from your childhood.
  11. Send a friend $5 for their next coffee. It’s on me today!
  12. Set up a virtual holiday gift exchange with your girlfriends. Send the gifts in advance and open them on screen!
  13. Drink champagne. Just because!
  14. Watch a Hallmark Holiday movie. ‘Tis the season.
  15. Call a friend you’ve not caught up with recently. It’ll be an instant mood-booster. Trust.
  16. Support Small Business Saturday. I can’t wait to shop my favorite Brooklyn spots. (My Small Business Gift Guide will also be live on Small Business Saturday and I have even more small business gift ideas here!)
  17. Hang some mistletoe. Festive and flirty.
  18. Buy holiday pajamas and new cozy slippers. *Sparks joy*
  19. Dress up! While we may not have parties as usual this year – dress up anyway!
  20. Try your hand at making a festive holiday cocktail. I can’t wait to scheme some up this year. (I actually shot one already so it’ll be coming to w&w soon!)
  21. Read a holiday-themed book. I recommend One Day in December and All I Want for Christmas.
  22. Send care packages to friends. Because everyone loves a surprise package.
  23. Listen to a great holiday playlist. I recommend mine!
  24. Do a holiday recipe exchange with friends or family. Share your favorites with one another.
  25. Buy and burn a holiday candle. These are some of my favorites.
  26. Don your favorite red lipstick! Seek smudge-proof for under your mask. (This one in Fraise is a personal holiday favorite).
  27. Have a virtual holiday party on Zoom with your friends or family. It won’t be the same but it can be just as festive with a bit of planning!
  28. Take a walk outside to take in your local holiday decorations. Always a personal favorite of mine this time of year!
  29. Buy a journal for 2021 memories and reflections. It’ll be good to look at in years to come.
  30. Attempt to make a family favorite recipe. For me this will be my mom’s Christmas sugar cookies! I’ve never made them at home and want to give them a go this year.

Here’s a fun image you can pin or save to your phone so you can tick through the list with me! I’ll be sharing what I’m doing on Instagram as I work through this list.

Stay Home Holiday Bucket List I wit & whimsy

And while the holidays in New York City will certainly not look the same this year, I also have a few NYC-specific items on my Holiday Bucket List this year! I know a lot of you often make annual trips to the city for the holidays and won’t be able to this year. It is my hope that I’ll be able to bring parts of the city’s festivities to you through my content this season!

I’m personally going to really miss annual favorites like seeing the NY Pops at Carnegie Hall and The Nutcracker at Lincoln Center but I am determined to soak up the city’s festivities safely + dress up for each occasion to make it feel a bit more normal!

New York City Holiday Bucket List:

What’s on your holiday bucket list this year!?


Look 1: Ann Taylor Star Pleated Skirt (4) // Sweatshirt (M) // Heels (Use code SARAHFLINT-MEGHAN for $50 off your first order)

Look 2: Ann Taylor Sweater (S) // Skirt (M) // Coat (M) // Heels (Use code SARAHFLINT-MEGHAN for $50 off your first order)







This post is in collaboration with Ann Taylor. Thank you so much for supporting the brands I love to work with! You can see our past collaborations together here, here, here.

[Pret a Provost Photography; Background photo of bucket list by kjpargeter for Freepik]

comments +

  1. Rebecca says:

    LOVE these fun holiday outfits!

  2. Katie says:

    Great list and lovely ways to give back! These are beautiful holiday looks. Ann Taylor is killing the midi skirt.

  3. Tomissa says:

    I’ve already checked off a few items on my holiday to-do list!

    2020’s holiday style is definitely comfort elevated.

  4. Jill says:

    Love this list! I’m really trying to buy everything from small businesses this Christmas.

  5. Amy says:

    I love both skirts! Especially the black tulle skirt. If only I had somewhere to wear it, it would be at the top of my list!?

  6. Kate Scott says:

    So many good ideas on your Bucket List – and LOVING these looks for holiday!

  7. Christina says:

    Love your list! I’m going to try and do all of these!!

  8. Mackenzie says:

    Love these ideas! Happy holidays!

  9. Melanie says:

    Love these skirts and the ideas! I’ve really been loving these lists when I feel down in the dumps or antsy to do something new… they’re filled with great ideas!

  10. angie says:

    I just ordered the green sweater!! Can’t wait to wear it + love all of your bucket list ideas for the holidays! xx

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