Sponsored

My Packing List for the Holidays

Packing for the Holidays

What are you doing for the holidays this year? I’m headed to Chicago to visit my boyfriend’s family (where the temperature will be… not warm) and then back east to spend time with mine. Activities include wearing matching pajamas and watching a lot of cheesy movies. Here’s what I’m bringing…

Packing for the Holidays

First things first, packing stresses me out. There are those people who can throw a bunch of stuff in a duffel in under an hour and easily make outfits for a week. I am not one of them. I make lists, lay everything out, and still worry that I’ve forgotten something. So, over the years, I’ve narrowed it down to the essentials.

When it comes to traveling to or from a cold climate, a packable puffer is your best friend. It’s there when you need it, then rolls down into nothing to squeeze into your bag or suitcase. (This one actually packs up into a travel pillow! Genius.) And a simple cardigan is a versatile piece, since it works equally well as a top or layered over a dress.

Packing for the Holidays

At home or away, I am all about a fleece pullover, for walks in the cold or watching a movie. Soft, teddy-bear-like textures are everywhere this season, and I am here for it. And because holidays can be stressful I’m training for a marathon, I always bring along black leggings and running shoes, for freezing cold invigorating morning runs.

Packing for the Holidays

No matter where I’m headed, my always-pack items are two pairs of trusty Levi’s, in blue and black, and a couple black T-shirts, for wearing alone or under sweaters. These items work with nearly everything else in my wardrobe, which takes the guesswork out of making outfits. (Anyone who knows me can attest I wear this combination almost every day.)

Packing for the Holidays

During the holidays, even a house party will often come with the directive of “festive” or “dress to impress.” So, whether I’m going to a soirée or just hanging out tree-side, I always throw in a sparkly item, just in case. A sequin topper — like this bomber jacket — is a fun statement piece over a casual outfit. (You can also make like a human disco ball and throw light all over the room.) To that end, I’ll also be bringing these pants, because why not.

Packing for the Holidays

My dog, Mia, finds packing even more anxiety provoking than I do. The mere sight of a suitcase sends her into a tizzy, as she thinks it signals that the people are leaving. So as a precaution, she usually packs herself. (And I always bring her, anyway. Along with one of these:)

What are you doing for the holidays? And what are you packing?

(Photos by Christine Han for Cup of Jo. This post is sponsored by Nordstrom, where shipping and returns are always free. Thanks for supporting the brands that help keep Cup of Jo running.)

  1. Anita says...

    Your dog Mia has a THIRD EYE. wow that’s SPECIAL.

  2. Dinah says...

    How do you travel with your dog? I need help or at least a trusted dog sitter friend :/

  3. Aly says...

    Love, love this post. Thank you so much!!

  4. Anne says...

    Did I see an insulated skirt in one of the photos? I’ve been scouring the Internet without success. Details please and thanks.

    • Meems says...

      I bought one from Uniglo. They came in a few colors WOMEN WINDPROOF WARM-LINED WRAP SKIRT and are on sale now. I wear it over leggings. The skirt snaps on and helps me go from Barre class to quick holiday errands in the “cold”.

    • Liz says...

      I have a skhoop one and they are fantastic – calf length for warmth, but they also sell shorter cute ones.

  5. Anna says...

    I work as a wardrobe stylist and I often do lay out photos for clients so they can get an idea of color palettes and textures while I’m still in the hunt-and-gather phase, and I do it with my own wardrobe when I start to think about what to pack for a trip. It helps so much to lay everything out on the bed and see what kind of outfits I can make. Then I take a pic so I remember later when I’m inevitably packing at the last minute!

  6. nicole underhill says...

    You’ll be getting great weather. 40s in December is unheard of! Enjoy the city.

  7. Sarah says...

    Love Oiselle. They have great winter running pants – and insulated long sleeves.

  8. Cici says...

    I just ordered the leopard pants in a frenzy for fear they would sell out.

    I’m not really a dog person but the story about Mia packing herself is too cute!

  9. Aly says...

    This the best “what to pack” guide. I already ordered a few things from the list. And I’m making note of the suggestions for all future packing. Thanks so much!!

  10. Michelle says...

    I love the sequined bomber, Caroline! We have a disco ball in our living room, hanging above the window and it’s magic around 4 pm. Being a human disco ball would be even better! (Unrelated, but I have to ask… the hand chair: can you actually sit in it without it toppling over? My husband has wanted one for years and I’d love to get one for him, but have to make sure it isn’t likely to injure one of our 3 munchkins or dog).

  11. Sally says...

    We’ll be off to my mums for an extended visit over the holiday.
    Our house always runs hot, whereas her old barn conversion always, ALWAYS runs cold (or seems that way to me), even when she’s got the heating on.
    Few things make me frustrated and grumpy quicker than being just a bit chilly when indoors, so I’m making preparations in the form of layers. Popping to the shops tomorrow morning to get a couple more thermal long-sleeve t-shirts and some fingerless gloves!
    My top-half layers go: vest, long-sleeve t-shirt, thick jumper.
    Bottom half: Thick socks, leggings, trousers.

    I’m going to be there the better part of a week, so – damnit – I’m going to be warm.

  12. Meredith says...

    Off topic, but I just sent this to my husband to study the bookshelves so we can have something similar after we move next year! I make heart eyes at Caroline’s shelves every time they grace Cup of Jo :) Major Library Goals!

  13. Karina says...

    That bomber jacket. Swoon!! A human disco ball? Omg I am so happy they are shipping to the UK. And I love Mia. She’s so tiny 😍

  14. Betsy says...

    My biggest problem with packing is my mood. I may pack something for every day of my trip, but I may not be feeling it at all. So I wear another outfit. But then I am short an outfit for later, or wearing something that I just am not feeling. I can’t be the only one?

    • Karen says...

      I am with you!! Always happens to me *sigh* lol

  15. Awads says...

    As a runner, I am here to tell you there is no such thing as “packing light” in the winter. Besides your stylish black tights and running shoes, you will need to pack the following: mittens, hat, light jacket, running shirt, multiple pairs of socks, additional layers. Count on another bag. But happy running!!! :-)

  16. Allyson says...

    I have that Madewell packable puffer and it’s SO warm & light. I think it’s weather rated down to 10 degrees. The slightly cropped & open bottom is really flattering. And I have packed it into a neck pillow for a road trip and it was great. Excellent find!

  17. Wink says...

    Am I the only one that was like: Pfffft about the clothes…let’s look at that bookcase?! Did a zoom and see lots of my favorites! Happy Holidays, Caroline, and good luck with the boyfriend’s fam!

    • cindy fried says...

      Seconded! Give us a shelfie…

  18. Allison says...

    I love Caroline and Mia!!

    • Joanna Goddard says...

      Mia is so adorable!

  19. Gaby says...

    Not going anywhere this season, but I have major packing anxiety and you’ve simplified my process for future trips 🙂

  20. Mouse says...

    Go to Le Bouchon in Bucktown with your guy for a classic warm French bistro experience. Been there a long time and it is lovely.

    Stay warm! I live in Maine, used to live in Chicago, and I have NEVER been so cold as when standing on the El waiting for a train in Chicago. Brrr.

  21. Well, I’m from Latvia, there are typical winters and summers. Now, for example it is supposed to be winter but it is unusually warm outside – 0 degrees after Celsium, usually it is snowy and minus 20 degrees after Celsium during Xmas time. So, have nice time in warm Chicago :)

  22. Lynn says...

    I travel frequently for work and for leisure. For work I’ve got a standard uniform pack; depending on duration 1 Banana Republic Sloan slacks, 2 JCrew slim stretch perfect shirt, 1 dress, 1 workout outfit + sneakers, toiletries, mini speaker, + my laptop bag.

    Weekend/long weekend trips in Europe are easy: two pairs of pants, 3 shirts, 1 layer top, 1 jacket, 2-3 pairs of shoes, 1 dress (and optional workout outfit depending on where we’re going). After each trip I do a ‘pack review’ and consider what I didnt need and what worked to refine for the next trip.

    It typically means our trip photos have me in the same outfit but a variable scarf here and there mixes it up.

    The one pack I’ve not mastered is the 2 week trip over Christmas because that duration means we’re typically moving about a lot and weather will be up and down. We’re headed to Spain with two distinct parts – skiing/mountains, and Andalusia where it’ll be around 18-20 Celsius. Wish me luck!

    Have a great holiday and enjoy!

    • Katrina says...

      This is BRILLIANT! Thank you for the specific style call-outs; I am looking for my version of a perfect, basic work shirt and pants (for a business casual office) and going to try the styles you listed!

      Does the JCrew slim stretch perfect shirt require ironing or is it OK right out of the dryer? Does it gap in the buttons in the chest area?

    • Heather says...

      I love having go-to business trip outfits, and it’s so hard to find things that are comfortable, professional, and look good right out of a suitcase – thanks for listing your specific items! One thing I like to do for business trips that are longer than 2 days is to draw a cartoony little sketch of the outfit I’m going to wear each day, including appropriate underwear and footwear, on a post-it note. It helps me think through what I need to pack, and is a useful reference during the trip so that I don’t accidentally wear/wrinkle the Day 3 pants on Day 1.

  23. sc says...

    this is awesome!

  24. WMom says...

    I live in Hawaii and work as a teacher. Tomorrow is my last day of work for the year. I will be wearing shorts and a tank top. Saturday night we fly to Sun Valley, Idaho where my parents live. I have will packing lots of squishy, fleecy long pants and sweaters. I am scared to go back to the cold, but excited to go snowboarding. I just hope I can find our snow clothes in storage.

  25. Mathilda says...

    I LOVE packing advices und lists thank you!!! I am wondering: I love fleece even though it is ugly. Comfy wins ;-) Well, at least it would if fleece wouldn’t give me “flying hair” so I never wear it. What do you do against it?

    • Joanna Goddard says...

      to combat frizzy hair, i rub just a little hand lotion into my hands and then smooth it over my hair. it works well! i wore so many fleeces during college at the University of Michigan and learned that trick there :)

    • Meredith says...

      Static guard misted lightly on your hairbrush and dryer sheets used very delicately on hair also help combat “flying hair!” Too heavy-handed with either too close to the roots can require dry shampoo to sort out.

  26. L.K says...

    I feel you! My packing routine is just anxiousness waiting to happen. It involves notes and a marathon try-on session to confirm everything works. It’s getting easier as I pair down my color palette to mostly black.
    The jacket that packs into a neck pillow is genius and Mia is just too darn cute!
    Have a great Holiday!

  27. Amy says...

    As far as sponsored posts go, this is one of the best!

    I’m glad to not have the stress of not doing any major travel during the holidays, but I have been craving a trip lately. I haven’t left my Canadian province in years – at least these provinces are pretty big, haha!

  28. Grace says...

    Yes, this can be a tricky situation to handle gracefully. Even fellow dog owners may not want lots of dogs in their home at once, or worry about how each animal will get along with the others.

  29. CB says...

    I’m a consultant and travel each week for work, and make it almost a journaling ritual for my packing system, which I get made fun of for all the time, but whatever, it’s great:
    1. Start with a notebook, and make large squares for each day/night outfit needed and number like a calendar; add high/low temps if weather is weird
    2. Label type of outfit (fancy, comfy, office) and fill in what you want to wear each day while sitting by your closet against day’s activities (I like a picture, or words)
    3. Pare down areas where you can double up, and add up to 3 shoes
    4. Add a box for workout stuff and non-clothes (once you do it once, use previous pages to copy)
    5. Lay out everything on the bed and ask yourself if this is how you want to feel on the trip; if it doesnt fit on the bed on hangers, you’re bringing too much, and visually you might realize one thing doesn’t belong (also, take a pic so you remember what’s in your bag for long trips)
    6. Pack it up, cross out as you go along, and roll out

    I can do this all in about 40 minutes, and it’s weirdly soothing. Plus, I have whole notebooks of what I packed and planned for dozens and dozens of trips, which is fun :)

    • Ally says...

      Great tip about the bed as a volume measure!

      Also matching to actual events/activities is essential as you point out, otherwise the tendency is to pack for imaginary, unlikely outings.

    • Madeleine says...

      This comment is as if Christmas has come early, CB. I have screenshotted it and plan to frame it. Thank you!

    • Eli says...

      What a fantastic idea! I am a list maker and do this in a list type way but this seems like a great evolution of it! Will definitely be implementing this idea for my upcoming trips. :) Cheers!

    • AMO says...

      This is brilliant! Totally trying this for my holiday travel.

    • Lauren E. says...

      I do the same thing! Only I use Excel. I find if I don’t, I usually end up packing multiple pairs of jeans that could’ve been pared way down, or three bulky sweaters when turns out, it’s going to be 60 and sunny all week. Friends laugh at my “packing spreadsheet” but it’s saved me so many extra suitcase pounds.

    • Joanna Goddard says...

      this is amazing, CB!

  30. Claire says...

    Caroline, how did you know? Between a holiday party with fellow teachers at my school and watching the presidential debate with my dad, somehow I have to find time to pack tonight. I’m also heading to Chicago to spend the holidays with my boyfriend’s family. I’ve never been to Chicago, but have always wanted to visit. Any must-do activities while I’m there?

    • Meg says...

      Chicago during the winter is beautiful! For a first timer, Cloud Gate, a deep dish pizza, the Willis/Sears tower, a late night in Wicker Park, and the Christkindlmarket are all fun choices. TimeOut also has a list of holiday light shows to check out.

    • Joanna Goddard says...

      Meg, those all sounds like so much fun! We took a family vacation to Chicago in the summer when Toby was a baby, and it was one of our favorite vacations ever! We biked along the water, ate at delicious restaurants and took Toby to the zoo. Also, I loved how there’s a beach in a big city — so rare! — and we loved how everyone stood in the water and drank beers. :)

    • Faith says...

      I second all of Meg’s recommendations (above), especially Christkindlmarket! If it’s not too freezing, I recommend visiting the lakefront, too, for the beautiful skyline views. <3

    • K says...

      Come to Chicago, CupofJo team!!! We can do a meetup!!!

    • Sandra says...

      Yes, those are all good options! Cloud Gate (known as “The Bean”), Skating the Ribbon Rink at Maggie Daley Park (there is another rink in Millennium Park but I feel like that is more crowded). The Christkindl Market is cute–get a boot mug of Gluhwein. There is a 2nd smaller Christkindl Market (and ice rink) up by Wrigley Field if either of you are sports fans and would enjoy seeing the stadium. I know people always recommend the cool neighborhood stuff, but on a first visit there is SO much to do right in the heart of downtown! The best view of the city skyline for photos IMO is out by the Planetarium (but SO cold out there!). If you want to see a view of the city from above there is the observatory at the Wilis (formerly Sears) tower. Or the observatory at the John Hancock building–which might have a new name now, I can’t remember. If you don’t want to pay to go up to the observatory there just go the the restaurant at the top and get a cocktail and enjoy the view. I feel like I’m the only one so blown away by the lobby at the Palmer House Hilton, but it is such a fantastic historic hotel. It’s a great place for a drink…just not during check in or check out time during the busy holidays. So many artists played at the Empire Room there in the ’30s–Sinatra, Judy Garland, etc.–and you can just feel the history! And the ceilings are stunning. I’ll have to defer to others for dining and nightlife options since we have a kid and moved to the ‘burbs so our recommendations would be outdated. Have a fantastic trip!

  31. ANDREA says...

    There are relaxing holidays at the end of the year!?!?!

  32. Paige says...

    This was such a good post! You guys always do sponsored posts SO well. They feel really authentic and natural. (Have a great trip, Caroline!! PS LOVE LOVE the bomber jacket!)

  33. Nora B says...

    BUT…..how come no one is talking about that AMAZING HAND CHAIR?!?! doubtful nordy’s sells that…..
    I’d love to hear the story behind that piece. Big hugs, Caroline, and safe travels!

    • olives says...

      DITTO!

    • Elizabeth R says...

      It is from Anthropologie. It was featured on her home tour a few months back.

    • Cate says...

      It’s from Anthropologie!

  34. Amy says...

    I’d like to start running outdoors in the cold weather – please can you share running gear for the cold?!?

    • AN says...

      Check out Tracksmith! Disclaimer: yes, it’s pricey, but their pieces are flawless and worth every penny–an investment in yourself, if you will! Their employees/models love running, every one of ’em, so they know what’s what in all kinds of weather. And runners are hard on their stuff! Plus the design and colorways are (kisses fingertips!). And, if you set a personal record in their clothes and take a photo, they’ll send you a gift card for $150. Seriously the greatest.

    • Alison says...

      I second Tracksmith clothing! Their long sleeve base layer is my favorite shirt to wear, whether I’m running outside or just running errands.

    • Eli says...

      I second Tracksmith! Former track and CC runner and I wish I’d had some of their gear so many years ago. I use a lot of their stuff for snow boarding and other activities and it is THE BEST! WAY better than anything Nike has every done with running clothes. Truly fantastic company and people. Plus, their journal and extra content really gets me into the feel and desire to run and pulls you back into the running culture (especially in a slump). Best of luck to you getting out in the cold!

    • liz says...

      oiselle and nike are also both good options that are a little less pricey but still high quality pieces (yes, i have issues with nike’s ethics, however, I find athletic wear to be the hardest to shop for with that concern, and I’ve literally been running with the same winter gear from them that I bought when I signed up for my first marathon 8 years ago)

  35. Erin says...

    love this post!! so fun to get a look into how others approach packing for specific destinations/events.

  36. Clare says...

    Caroline – I’m from Chicago. Some Chicago spots I think you’d like: Daises (homemade pasta & great veggie sides in Logan Square), Lost Lake (fun tiki bar that really decks the halls for Christmas), Myopic Books (used bookstore in the heart of Wicker Park) & around the corner from must-try falafel at Sultan’s Market (super cheap & cash only but they have an ATM). Grab breakfast, lunch or dinner at Spinning J (cutest & delicious spot run by husband/wife duo) and then stop across the street at Peach Fuzz for some of the cutest gifts for kids & adults. Hope you enjoy!

    • Faith says...

      I lived in Chicago for 8 years and Sultan’s Market was our go-to place for takeout. Delicious!

    • Kate says...

      Oh my god, I ate at Daisies for the first time this summer and I think about that meal at least once a week. The pasta was unreal. My other favorite meal that trip was in Pilsen at Monney Burke’s. Chicago food is amazing!

  37. Jan says...

    Um, can I have your dog?
    Please,
    pretty please,
    with sugar on top

    • Joanna Goddard says...

      hahaha

  38. Sarah says...

    But where are the leopard pants from!??!

    • Caroline Donofrio says...
  39. Monica says...

    I always love a Caroline post and even better when sprinkled with animal prints, sequins and Mia! It’s like a little CoJ present today. ♥

  40. liz says...

    love this post (and your bookshelf)!

  41. Cynthia says...

    Caroline, please share how you ask hosts if you can bring along your dog! It seems like a big ask to me what with potential allergies, expensive rugs, people who choose not to have pets, small children living in the home or also visiting, and so on. Even with a perfectly behaved, elderly, tiny, docile creature it can’t always be easy. Is is a deal-breaker for you: we both come or we won’t come?

    • Sonja says...

      I would love to hear the answer to this as well! <3

    • Leigh says...

      Me too. We have cats so we would not be able to have someone bring their dog. I would hope a guest would ask first.

    • Mae says...

      I can’t speak for Caroline, but I have traveled with pets off and on over the years (due to pet age, lack of pet sitting options, monetary status, etc., other situations), and I’ve always asked the hosts, and/or it was something they offered outright when extending the invitation. You tend to have a good idea or have covered topical ground like that prior to coming to stay with someone, I think. But, goodness no, I’ve never just shown up with a dog or cat.

      However, I think it’s worth a mention that folks with kids ought to also think about this one, too! With the exception of allergies, the other issues Cynthia mentions also apply as potential problems for bringing littles with (expensive items and rugs, resident pets that may not be okay with attention from small children, houses that are just sooooo child unsafe that it’s impossible to do so for a visit). Again, I ALWAYS ask when traveling with my kiddos to make sure, but I get the sense that many people don’t?

  42. MJ says...

    This is the cutest post.

  43. Kelli says...

    This running geek is requesting a separate post with all of your marathon training details! Which race? How is training going? What inspired you to tackle the distance? What is your go-to post long run meal? All the details!

    • Mary says...

      I’m a walker not a runner but how do you keep your hands (fingers) warm in winter? I walk at night after work and it’s chilly in NJ!

    • liz says...

      this is going to sound basic but: gloves! and honestly, if you’re running and its not under 20 degrees, you’ll warm up.. I always end up pulling mine off half way through my run and carrying them because I get too warm. also if its super cold, might layer a thin glove under a thicker pair

  44. katie says...

    I’m headed to my Mom’s in NorCal for Christmas, and my thing is: always pack a swimsuit. You never know when they’ll be a chance to swim or go for a hot soak somewhere! Plus, it takes up zero space ;)

    Also a huge fan of taking your dog(s) with you if you can (in my case, yes)…not only for their steady companionship, but also cuz they’re a built in excuse to take a long walk at least once a day. Good for you, them, and your whole family.

    Have the most fun, Caroline!

    • Alice says...

      My boyfriend ALWAYS does this! Anywhere we go, he packs one. I’m now learning to do so too, as he’s previously booked us into a load of places with spas that I haven’t known about in advance and then can’t enjoy them. It’s such a good tip!

  45. Sarah says...

    I’m typically a light packer (did three weeks in Europe out of a carry on this summer!) but cold weather sets in and all of a sudden I need to pack every oversized sweater, blanket scarf, and stretch pant I own. Plus comfy socks and house slippers. I am a bring-my-own-coziness type of traveler :)

    • Lisa says...

      I am exactly the same way! I need to have all my cozy clothes and a blanket from home just in case I get cold:)

  46. EliseB says...

    Please, more about Mia the Adorable. Is she a Yorkie? Thanks?

    • Caroline Donofrio says...

      Sure! Mia is a Yorkie/Maltese mix and will be 12 in February. She’s very cuddly, has a lot of opinions (mostly around when dinner should happen), and is easily the best buddy, ever. :)

    • EliseB says...

      Caroline, Thank you your reply. Mia is wonderful. So glad you have her. Dogs are special, dear beings.

  47. Daniela says...

    It’s just my hubby and I for the holidays this year and I’m honestly excited for this (our first married Christmas!). We will be lounging fireside and enjoying a nontraditional Christmas dinner, all while I wear my ugly Christmas sweater and leggings (that do not match at all). Considering switching to matching pajamas/onesies though.. We’ll see!

  48. Molly says...

    The temps may be warmer than you expect, Caroline—I see the prediction for Christmas Day is 45F.

    • MRM says...

      Yes, I was going to point this out. It will actually be really WARM here (in Chicago)!

  49. Beth says...

    Go for a run along Chicago’s lakefront trail! It inspires me every time, allows for long distances without dealing with traffic and gives you one of the best views of the stunning skyline. The community along LFT is the best.

    Seasons greetings from Chicago!

  50. RN says...

    But what do you do for cropped pants in freezing weather? Socks? High boots? Halp!

    And have a great trip :)

    • Caroline Donofrio says...

      I swear by the cropped pants because I am what I like to call a cropped person. :) I appreciate the straight leg fit and how (on my 5’2″ frame) they hit me just above the ankle. But yes, in the winter I wear them with socks and boots. Or, if it’s not too freezing, high top sneakers. Hope that helps!

  51. Allison says...

    yay for running a marathon! which one?!