Packing for a Winter Vacation

I don’t do a ton of traveling, but I do my fair share. No matter how much I travel, I’ve never learned to pack lightly. Anytime I try to pack less, I always regret leaving something behind, so I’ve decided to embrace my overpacking tendencies and call it charming. My husband isn’t so convinced, but he’s learned not to fight it. Ha!

All that to say, this post is not really advice on how to pack (unless you like feeling like a packmule.) Rather, I’m just sharing how I pack.

Packing for a Winter Vacation

Details: 26-inch suitcase | plaid scarf | pink turtleneck | DL1961 Emma skinnies | similar riding boots | black quilted vest | similar down coat

My family was scheduled to leave early this morning for Maine. It’s been pouring rain for the past 12 hours, and the weather system is moving up the east coast. The folks in Maine are supposed to get 10-12 inches of snow today. We had high hopes for getting there, so we were completely packed when we went to bed last night, but alas, as we were waking the kids from their slumber at o’dark-thirty this morning, I got the call. Flight cancelled.

We’re still trying to figure out if we can get to Maine today or not, but in the meanwhile, I thought I’d show you what I packed in case you’re planning a similar vacation. Perhaps it will be helpful. Or maybe you can give me some tips for packing lighter!

Packing for a winter vacation is quite different than packing for a summer one, I’ve discovered. For this trip, I have one entire suitcase dedicated to snowsuits and boots!

I didn’t take pictures of the other suitcases, but I did snap a few of my own.

When I pack, I usually start out by planning what I want to wear on the plane. Then I can take into account those shoes and accessories when I plan the rest of my outfits. While I don’t try to pack light, I do attempt to bring as few shoes as possible, especially in the wintertime because they add so much weight and bulk to the suitcase. That means finding outfits that work with the shoes (and the jeans) that I wear to travel. This is my travel outfit today.

travel outfit - 1 (1)

I also added my black quilted vest to the ensemble, even though I’ll be wearing a winter coat. I tried to pack it, but it’s too bulky.

Here’s a look at my suitcase, all packed and ready to go.

suitcase - 1

I always try to pack a small suitcase, but I usually end up with a mid-size one. This is partly because I am determined to pack my hairdryer. I LOVE this thing, and I refuse to use the crappy ones in the hotel rooms. I like to buy travel sizes of my shampoo and conditioner so I don’t have to carry big bottles, and that’s my favorite “big round brush” that I use to style my hair.

I pack my makeup in this Stella & Dot Ikat Beauty Bag. At home, I keep it in a pull-out drawer where I can see everything easily, but for travel, it fits neatly in this bag. I also throw my toothbrush, toothpaste, contect lens case, and a travel size contact lens solution in there.

Finally, I packed my Rodan + Fields Redefine skincare regimen. I have recently signed on to be a distributor, and so far I love the products. I’ll share more after I’ve used it for a while.

suitcase - 1 (2)

Besides my toiletries, I packed my running shoes, my Athleta Metro Skinny Pants, a comfy hoodie, and my black jeans. The Metro Skinny Pants were for hanging out around the house, and if I did get up there and find the streets conducive to running, I could run in them as well. Fortunately, we have a washer and dryer where we were going. Right now those pants are on sale for $47.99, which is practically unheard of, AND they seem to have all sizes available. They’re great because they look nice enough to wear out and about, running errands and taking the kids to and fro.

On the other side of my suitcase, I packed my slippers, pajamas, and the rest of my clothing. I did cheat a bit, as I put my Sorel snow boots in the big suitcase with everyone else’s boots and snow gear.

suitcase - 1 (1)

In addition to the outfit I was planning to wear on the plane, I have the black jeans, a cardigan (similar), a turtleneck, 2 crewneck sweaters, and a long-sleeve tee for layering. My riding boots will go with everything, but I figured I’d probably be wearing my Sorel snow boots when we go out.

I also packed two scarves (fringe infinity and similar grey leopard) and some of my favorite jewelry. I usually wear diamond studs and my Alex and Ani bangles on the plane because they go with everything. Then I will pack a few other options, depending on what clothing I’m bringing, but I try to keep my jewelry as minimal as possible. No one cares if I wear the same necklace every day! In this case, I wore my Silpada chevron plunge necklace, and it will pretty much go with everything in my suitcase.

And that’s it! I didn’t do too bad for a high maintenance over-packer going on a 5-day winter vacation, did I!?!

This is a 26-inch Hardside Expandable Spinner Suitcase. We have several suitcases by this Ricardo brand, and we’ve been quite happy with them. I’m in the process of switching all of our luggage over to this set. It’s lightweight, it rolls easily through the airports, and it’s held up well for us. They’re on sale right now at Macy’s, for a pretty sweet deal.


I like the 26-inch size a lot. I have a 30-inch size that I used to use, but I was always going over the weight limit in the airport, and it was really cumbersome to transport, so I bought this 26-incher, and I’ve never looked back. We have two of the 21-inch size, but it is too small for most of my trips. My husband likes it, though, when he goes away on business trips, and when we travel as a family, we use one for my girls. Even if I’m only gone for 2 nights, I still need my hairdryer and all of my toiletries, so I usually end up in my 26-inch suitcase before all is said and done. For me, that’s the perfect size.

Unfortunately, my suitcase will not be making it to Maine today. Air travel is a bit of a mess right now, what with the tornados out west, the holidays, and now this weather system coming in from the midwest. When I finally got an operator on the phone after listening to bad elevator music for almost 30 minutes, I had to make a split second decision whether to chance it on another flight or not, and we decided to stay put.

I can’t say that I’m at peace with my decision, but what’s done is done. Winter travel is always a bit of a gamble, and you’ve gotta do the best you can with the information you have at the time. Maybe there’s a reason we were meant to stay here, or maybe it’s just another one of life’s cruel jokes, but we’re here nonetheless. Anyone free for New Year’s Eve?

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30 Responses

  1. I think you did a marvelous job of packing! And, no, I don’t think you packed too much (now I didn’t see the rest of the luggage y’all took along ;-)…) I’m considered a ”reasonable” packer, my daughter, on the other hand, takes enough along to outfit a village – you’re closer to my packing style… So unless you need to be concerned about carrying anything that’s too unmanageable looks like you’re good to go! Weather permitting:-(

    1. You know, this is probably the most efficient packing job I’ve ever done! LOL!! I even threw another running top in there just in case, and I still have room! Maybe I AM getting better. 🙂

  2. Jo-Lynne, I am so sorry your trip has been cancelled! I look at it that there is a real reason & that God is protecting your family from something. Maybe you can come up with some special things for the family to do that’s close by. Or maybe each of your children can pick something to do on a specific day.
    I think you are a smart packer! The only thing I would have done is swap out one of the sweaters for another turtleneck & add another necklace.
    I know you will make it a Blessed day!

    1. Thanks, Ginger. The second guessing myself is the worst part. It looks like some flights are getting to Maine today so we probably could have made it work, but I was afraid of getting stuck at the airport. Anyway, yes, perhaps God was protecting us from something. We’ll probably never know. Our after-Christmas travel plans keep getting thwarted, which is very frustrating. This is the 3rd year in a row. Bah humbug. 🙂

      1. I would definitely take this as a sign that for some reason your family is not supposed to travel after Christmas. Maybe start thinking of a new tradition for 2016.
        ???? ☕️ ????

  3. I’m a horrible overpacker too, so your suitcase looks perfectly reasonable to me. Bummer about your trip. Since they cancelled, I hope that means you won’t lose your money.

  4. I discovered packing light.com when I took a 14 day trip to Europe with only a carry-on size bag and backpack combo I got at Sam’s Club. The site has a video for instructions on how to pack. You would be amazed at how much you can fit in that small space! That is the only way I pack now.

    1. You’ve done a great job! Another thing you should check out are packing bags and packing cubes. These save space and keep me organized. I have traveled to Europe twice for 25-30 days using a carry on and a backpack style purse so I’ve developed a lot of tricks. I’ve found that once I committed to traveling lighter I never used my big old suitcase ever again.

  5. Just bought the metro pants from Athleta! Would love to see you do a post on stylish comfortable/active wear. Or perhaps some of your favorites from Athleta. I struggle in this area. So sorry about your travel plans! Hope you are able to enjoy some family time closer to home this week! Thanks for all you do!

  6. I’m sorry about the disappointment with your trip! I have terrible Airline Karma. I think I must have been a horrible, obnoxious traveller in a past life or something. I decided a few years ago, after my luggage was sent to a different CONTINENT than me for 3 days, to only do carry-on, and although that sometimes means I spend part of my vacation hunting down a washing machine and I am wearing the same outfit in nearly every picture, it also means I am (almost) guaranteed to arrive with all my belongings. I’ve found the Une Femme D’Un Certain Age blog incredibly helpful for packing suggestions.

  7. I’m so sorry about the trip cancellation. But yes, Maine is getting hit hard with snow right now. Wish we could have some of that! Great looking suitcase, I’ll check them out, and YOU look fabulous wearing that scarf! xox

  8. The weather here in Maine today is very messy. We are lucky though, outside of Portland is all snow. Sorry to hear your flight was cancelled. Maybe you can come to Maine over February vacation and enjoy some skiing.

  9. Ok, so I have a question that I have never had the courage to ask and only feel like I can now due to the relative anonymity of this site. It’s rather personal, so I totally understand if you don’t want to answer it. I just ordered the Athleta yoga pants that you recommend and my question is…What kind of underwear do you wear with these kind of pants that don’t show panty lines. Now, I can wear a thong when I need to, but it’s definitely not the most comfortable thing in the world. So, when I think about lounging around in comfy yoga pants, I don’t particularly want to wear a thong. But I hate seeing panty lines with these. Most of the ones I’ve had still have panty lines even with my “good” panties – I guess b/c they are more fitted. I wear the Soma vanishing lines. Anyway, if you feel comfortable answering, I would love some guidance on this little dilemma. And even a suggestion for great panties would be good!

    1. I SWEAR by the seamless hipster panties from Lululemon…they are around $18 a pair but you can’t see a thing with workout wear….and I like a full back on my panties!!!!! Fabletics has made a similar pair but they aren’t quite as good….much more reasonable though!!! Hope that helps! 🙂

      1. Thanks so much Amy! I tried to find these on the website and couldn’t find them. Do they go by a different name? I googled and found something they make called “light as air” hipster, but that didn’t even show up on their website. Maybe they’re just all sold out??

  10. I used to pack all of my favorite clothes for that season when I traveled. What cured me was having a checked bag get “lost” for several days by an airline. Now I pack a capsule wardrobe, in carry-on luggage. The website The Vivienne Files has great ideas for coordinated packing. One hint: wear the bulkiest items (coat, shoes/boots) on the plane.

  11. You did a great job with your packing. I need to take some tips from you – seems like I always pack way too much. Sorry your trip was cancelled!

  12. My suitcase *never* looks that neat! And I don’t even come out looking as cute and put together on the arrival end…sigh. Love your travel look. I might have to pick up a blanket scarf.

  13. I’m impressed! I think you did great! I feel like I take this much on a 3 day business trip! I too am a hair dryer snob and always bring my own + the diffuser! I also sneak in my pillow as I hate the thick hotel pillows and love my flat/feather pillow if leaving for more than 1 night. Hope you enjoy your extra days around the house and still get to relax!

  14. I do fairly well with packing shoes and clothes, where I have problems is toiletries! I think I take something for every possible emergency, which is probably pretty dumb, especially if I’m in the US still. Also, I hate packing jewelry, it gets tangled and I’m scared to death I’m going to lose earrings, etc., so now I just wear one set of jewelry and that’s it! I find packing extremely stressful, and I think as I get older, the more it stresses me out! I appreciate the tips!

  15. Oh my goodness I bought the Athleta metro skinny pants and love them! In fact I bought a second pair today. They are incredibly comfortable. Thank you for offering such great style advice!

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