6 Strategies for Packing Lightly: How I Traveled Cross Country in Winter with Just a Personal Item

Here’s everything I brought with me for a two-week-long trip to Vermont - packing in just a “personal item” for the plane.

The weather in Corvallis is finally warming up enough that I’ve switched over my winter wardrobe for my spring/summer wardrobe. Doing so reminded me that I had this post lingering in draft mode. Figured I’d better get it out there!

When I booked my flight to Burlington in anticipation of Jumping into Tiny House Design-Build Cert 2025, I snagged the least expensive flight I could find that fit the schedule. That meant signing up for a ticket that included a personal item, but no carry-on luggage. I knew that was going to be a feat considering that I was packing for two-weeks… in Vermont… in winter!

I’d need things for both the design studio and the build site. But I’ve learned How to Travel with Just a Carry-On. When I traveled the world last spring with just a carry-on and a personal item I was able to do it because of My International Travel Capsule Wardrobe. I even found there were a few times I was able to downsize from my carry on to my personal item for a few days of travel and that was so freeing! So I took the personal item as a packing challenge.

When I booked my flight to teach Women’s+ Basic Carpentry just three weeks later, my ticket included a carry-on bag. But I figured since I’d successfully packed in just my duffle backpack for a similar trip to the same place in a similar season, I could just repurpose my packing list and do it again. No need to reinvent the packing list. I realized I could probably bring even less since it might be warmer and I’d be mostly on the job site rather than in the design studio. The course was also half as long (though, as I noted in Packing Lightly vs. Packing Densely, I’ve learned I don’t need more for 3 weeks than I do for one.)

As I started packing for the second trip I was grateful that I’d done what I do on most trips when I’m at the airport on my way home: review my packing list and make notes about what worked and didn’t as a reference for future trips. I recognize for most people this is overkill and they just want to go on a trip with the stuff they love best right now. I get that. I appreciate it. I just can’t seem to help travel hacking my own systems. I’ve learned a lot and it serves me well. It might not serve you. That’s fine, of course. But since I’ve benefitted from checking out other people’s packing lists (especially when it comes to building capsule wardrobes), I’ve decided to share my packing-in-a-personal-item strategies here in case they’re helpful for anyone else.

First, let me caveat that I am a smallish human and bigger people with bigger clothes would have a harder time. Let’s just say all that getting teased as a kid for being short does have this one payback! Second, my Osprey Arcane Duffle Pack is not technically the size allowed for a personal item on Delta. Their maximums (in inches) are 9x10x17 and this pack is 10.5x12x18.5. So, if it’s fully packed, this bag doesn’t qualify. But those numbers are darn close and it’s quite squish-able, so I figured I could make do. And I did!

Here’s my “personal item” all packed, along with the clothes I wore on the plane. Ready to go!

Strategy #1: Wear it on the Plane

I knew the only way I’d be able to pull this off was that I’d be wearing some bulky things on the plane. Since what you are physically wearing doesn’t count in the baggage allowance I figured I’d just wear my bulkiest stuff for my travel days. On my first trip I wore:

  • under things

  • long underwear

  • jeans

  • zip-up fleece with pockets stuffed with gloves

  • a reversible infinity scarf

  • arctic Muck boots

  • and I alternated wearing and carrying my long winter coat (with pockets stuffed with ski gloves and a headband) depending on how warm I was

On my second trip I decided to ditch the long winter coat, so I wore my Proviz jacket, but otherwise, the same outfit.

Here are the two pairs of footwear I brought on my winter trip. For summer trips I usually bring a pair of sandals and a pair of lightweight shoes.

Strategy #2: Minimize Footwear

So many years of tiny house living has me really good about taking off my shoes at the door. And a little more than 3 years of living in Vermont taught me to travel with my slippers from October through March. Slippers have become such an essential that I often bring them even if I’m just going to a friend’s house for dinner. It feels very Japanese to wear slippers even in other people’s houses (and rather luxurious), so I highly recommend it!

When I was packing for the first trip realized I could probably get away with just my arctic Muck Boots for outside (on the job site and walking around town) and my slippers for inside. Most of the time I wouldn’t teach in slippers, but Yestermorrow is casual. If I was in a more formal setting I would have brought something that wasn’t technically slippers, but kinda felt like it, like the Tom’s I thrifted. I love having a Mr. Rogers moment of changing from boots to slippers at the door.

Here’s the uniform I wore on the job site: long underwear, work pants, fleece, puffer.

Strategy #3: Pick a Uniform

If you’re going to be in a situation where no one is going to care what you’re wearing, wear the same stuff over and over again and just don’t worry about it. (And if you’re traveling people won’t know what you wore yesterday or the day before so bonus points to you!)

My “uniform” on the job site was:

  • long-underwear under carpenter pants (fleece for first trip when it was colder and wool for second when it was warmer weather)

  • long-sleeve wool shirt

  • down vest

  • long-sleeve zip-up fleece

  • rain jacket

  • fleece headband

  • gloves

  • socks and Arctic Muck boots

I didn’t need all of it on all the time, but being able to layer up was super handy, and I didn’t have to put thought into what I was going to wear. I knew it would be cold while building in the airport hanger in the winter, so sweating through my clothes wasn’t a concern. In the summertime I’d just replace all the warm layers with tanks and t-shirts and I’d bring a brimmed hat.

Here are some of my mix-and-match studio clothes.

Strategy #4: Bring Mix & Match Outfits

For the design studio, field trips, and trips into town I wanted a couple casual outfits.

On my first trip I brought 5 bottoms:

  • black bamboo long underwear

  • black cotton leggings

  • brown cotton leggings

  • blue jeans

  • a down skirt

And I brought 2 tops:

  • a black bamboo long sleeve

  • a teal wool long sleeve

I was able to layer the bamboo long underwear under jeans or leggings if it was super cold out. I could wear either pair of leggings with the skirt. I could wear either shirt with any bottom combo. I could add my down vest or fleece from my job site wardrobe if I needed more warmth. I could accessorize with my scarf or my buff. So I had a number of different outfits I could pull together with just these few tops and bottoms.

For my second trip I brought just the black leggings and I skipped the bamboo leggings and the brown leggings. I think next time I’d skip the wool ones and bring the bamboo since they’re softer.

Here are the three pairs of Boody bamboo undies I brought, along with two pouches: one for clean and one for dirty.

Strategy #5: Plan to Hand Wash

The first time I saw an ad for travel underwear, saying someone traveled for a long stretch of time in several countries with just one pair of underwear, I was incredulous. “Or maybe two…” they said. And it clicked. Two I could understand. I’ve been traveling with three pairs of undies ever since. My motto is: “one to wash, one to wear, and one cuz life.” When I was traveling internationally I found I actually needed 4 pairs because I was on the go often enough that I didn’t always have time for undies to dry. But when I’m staying in one place night after night 2-3 pairs of bamboo Boody undies and 2-3 pairs of socks work just fine. Washing undies and socks is just part of the nighttime ritual, like brushing my teeth.

Here are all my pods, ready to be packed into my “personal item.”

Strategy #6: Pack in Pods

I’ve been packing in pods for so long I can’t remember when I started. Two zippered mesh bags hold most of my clothes, usually rolled to maximize space. For this trip I put studio clothes in the gray one and work site clothes in the navy one. I have two small pouches I use for undies (clean and dirty), another small pouch for socks, and another for jammies. I use a Sea to Summit toiletry pouch that’s TSA friendly and a sleepy time pouch with earplugs, a headlamp, an eyemask. In the past I’ve also used an electronics pouch, but I didn’t need much tech on this trip, so didn’t bring it.

Have you used any of these strategies for packing lightly? Any you think you might try? What are your favorite traveling lightly strategies?