Packing is not usually a strength of mine, I generally pack far more than I actually need. However, on a recent trip I feel like I packed my carry on perfectly. Packing for cold weather is the most difficult because I only want to pack sweaters, which are bulky. In this post I’m sharing some tips on how to pack the perfect carry on for a week in fall or winter weather.
Pack Around Your Schedule
On this trip we were traveling to the Boston area and the temperature was going to be in the 50s. So technically this was fall weather, but I think this packing strategy is applicable for winter weather as well. The only difference would be the kind of jacket you bring, which you would wear on the plane.
On this trip we had specific days we had planned out and some “free” days. I started by deciding what I wanted to wear on which day. For example, I wanted to wear my new LOFT sweater when we went to Salem and I had a specific sweatshirt for a football game. These items are what I packed first.
Packing Quantities
I like to have options, which is why I generally overpack. And usually I overpack tops. This trip was going to be strictly casual attire but I selected sweaters that could look dressed up if appropriate. Here are the quantities of each article of clothing I packed/wore:
- Sweaters/Sweatshirts: 3
- Light long sleeve shirts: 3
- T-Shirts: 2
- Jeans: 2
- Jacket: 1
- Sweatpants: 2
- Boots: 1
- Sneakers: 1
- Scarf: 1
If you notice, one thing I did not specifically bring was pajamas. I slept in the t-shirts and sweatpants I brought and wore them a few times, just to bed.
Color Planning Around Shoes
I knew I wasn’t going to be able to fit multiple pairs of boots in my carry on so I chose one pair of booties to bring that would be easy to walk in. These were black Timerland booties from DSW. They are comfortable but still cute! I also packed a pair of tennis shoes in case we wanted to go for walks and be active, these were much easier to pack in the suitcase.
Since I was going to wear these black boots likely everyday I made sure that every top I packed would go okay with the boots. Luckily this was easy to plan since these boots are very versatile.
7 Days of Outfits With A Carry On
Below I have listed out the outfits I wore on everyday of the trip and a summary of the activities we did.
Day 1: Flight
To plan what I would wear on the plane, I started from the bottom. The booties I was going to bring would take up a lot of space so I couldn’t pack them. I also decided to wear jeans and a sweater since they can take up a lot of space. Finally, I wore my rain jacket over all of it.
Note: be sure to check for rain. I probably would have brought a different fall jacket if rain had not been in the forecast.
Day 2: Casual Day
On this day we drove around Cape Cod and spent time with family. This sweater is actually very light so it was easy to pack.
Day 3: Visit to Provincetown, MA
This is one of my favorite outfits of the trip! This light sweater goes with so many things, but most of all I love this scarf from DSW, unfortunately I cannot find it in this color online.
Day 4: Boston College Game
We tailgated and attended a football game on this day which was a lot of fun. This Boston College sweater from Amazon was one of the bulkier items I packed, but worth it because tailgating early in the morning was quite chilly.
Day 5: Casual Day
This light top from Target hardly took up any space at all when folded up. It was perfect for a more casual day where we went to dinner and a movie.
Day 6: Trip to Salem
Another one of my bulkier items was this sweater from the LOFT. One of my favorite days of the whole trip was when we went to Salem, I wrote a blog post about it which you can find here.
Day 7: Return Home
For the return flight, I might have worn the Boston college sweatshirt again. I didn’t document it since it was an early flight and we were home within four hours.
Other Ways I Saved Carry On Space
My toiletries and makeup bag can always take up a lot of space. I made sure I only brought the makeup up I really needed and would use. If you can, keep it to just one eyeshadow palette. However, I couldn’t decide and packed two.
A big way I saved on space, which made going through security easier, was by not packing many liquid items. I only packed my moisturizer. Then, when we arrived in Boston we went to Target and grabbed the toiletries which included: shampoo, conditioner, dry shampoo, body lotion and toothpaste.
Packing cubes are another lifesaver for me. They help keep everything organized and I think they help me to save room. I have used these packing cubes for years, and I can’t stand to travel (even for short weekend trips) without them.
Once everything was packed, I realized I could fit more clothing in my carry on if I wanted. However, I loved that I had extra room because this meant I could go shopping while I was there.
I hope this post has been helpful! If you follow these tips (and are okay with wearing some items more than once) you should have no problem packing a carry on for fall or winter travel.
Thanks for reading!
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