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?