I used to be an infamous over-packer. When I was packing for a trip, I would always pack way more than I needed, usually double the amount that I needed. I remember packing for a 2 week trip back in 2005 and I had an extra large red suitcase, the biggest one that you could buy, that I stuffed!

The weight scale used to be my best friend when I was packing to go somewhere. I would pack everything and then weigh the suitcase to see if it was over the weight limit. Normally it was, so I would take some things out. This usually helped me squeeze by at the check-in counter, but there were times when I got up to the counter and I had to remove items from my bag and put them in my carry on.

If you’ve never had the experience of having to open your suitcase in the middle of checking into a flight, in front of a bunch of strangers, and then select what you thought the heaviest items were, you’re simply missing out. I kid.

But once I discovered minimalism, I learned to only pack the things that I need. That means that when I go on trips now, I use all of the things that I bring. The added bonus is that unpacking once I get home is so much easier. I simply toss most of the items in the laundry basket or hang a few items back in my closet, as opposed to having to hang half (or more) of the unworn items back up.

A Weekend Trip

I just recently had a girl’s weekend in Chicago. I thought it would be fun, and hopefully useful, to show you how I packed for it. I left home on a Friday and returned on a Sunday, so 2 days and 2 nights in total.

There are a number of things that I take into consideration before I go on any trip, namely the weather and the activities that I will be doing once I’m there.

The Weather

The first thing that I did was look at the weather that we would be having. The temperature for Friday and Sunday was going to be in the 90s with sun. Saturday was supposed to be cooler in the 80s with scattered storms throughout the day.

The Activities

Then I thought about what activities we would be doing.

The plan was to visit Navy Pier on Friday afternoon once we got into Chicago. We were all craving Giordano’s Pizza and fountain pop. Then we were going to walk around for a little before heading back to the hotel to get ready for dinner and a night out.

Saturday was to be much of the same with lots of walking around during the day and dinner in the evening followed by a night out.

Sunday was going to be breakfast and then the drive home.

The Outfit Plan

I decided that packing one outfit for each day (from my Project 333 capsule) and one outfit for each night (I ended up picking one dress outside of the capsule for Saturday night) would be ideal.

In total, I had 1 tunic, 1 pair of pants, 1 romper, 1 dress, 1 jumpsuit and 2 pairs of shoes (1 sandal, 1 heels).

I used accessories from my capsule (1 pair of gold hoops, watch, gold necklace, self made long necklace).

I also took a sweater from my capsule to have in hand in case I got cold.

Friday

I had started the day in these pants and a black top with pink slides, but decided to change the top and shoes at the last minute since it was going to be quite warm in Chicago. I wanted something that would be comfortable for a long car ride.

The outfit consists of my grey Flax linen pants, white Ozma of California silk cami, Eileen Fisher sport sandals, gold hoops, my gold stingray necklace, and Skagen watch.

Friday Night

The plan for the evening was dinner at a Mexican restaurant followed by drinks and dancing at a Piano Bar, specifically Howl at the Moon (highly recommend this place if you’re ever in Chicago). It was still very warm so I kept it cool and simple with a black Mossimo romper, tan heels, my simple gold hoops, and Skagen watch.

Saturday

Since there would be lots of walking around, I wanted something that would be comfortable. Luckily, it was a bit cooler and this outfit, consisting of my grey Eileen Fisher tunic (tucked in), printed Lululemon pants, Eileen Fisher sport sandals, gold hoops, self made long necklace, and watch, was perfect!

Saturday Night

The plan for that evening was to go to dinner at a sushi restaurant and then go to a nice bar for drinks. I decided to wear a white printed dress, which was selected outside of my capsule wardrobe, tan heels, gold hoops, and my watch.

Sunday

The long drive home. Again, comfort was key so I wore my striped Linenfox jumpsuit, Eileen Fisher Sport Sandals, gold hoops, and watch. A perfect travel outfit!

The Luggage

The bag that I use is a carry on backpack that I bought back in 2015 when I started my minimalist journey. That year we were traveling to Canada for 2 weeks and I really wanted to try traveling with a carry on only.

After doing extensive research, I settled on a Tortuga travel backpack. The model that I have is no longer available but it is closest to the 45L Outbreaker Backpack. What I like the most about it, besides all the pockets, is that it can be a backpack (with a great hip strap to help with the weight) or you can conceal the straps inside of a zippered panel and carry it like a briefcase.

I have used this backpack faithfully for the past three years (my husband also uses it when he travels solo for work) and it has held up wonderfully.

I like to roll my clothing and if an outfit consists of separates (such as Saturdays’s outfit), I roll them together. I pack toiletries (top bag below), intimates (middle bag below), jewelry (bottom bag below), and shoes (in the carry on below) into separate bags. This keeps everything neat and contained. It also makes it easier to find things once I’m at my destination.

I always keep my makeup in a blue plastic pencil case and this fits perfectly in one of the zippered mesh pockets. I put hair products (hair straightener, hairspray and dry shampoo) in the other zippered mesh pocket. This bag has two additional zippered pockets that I did not use on this trip, but I would use these to hold larger accessories (such as a belt or scarf), or socks in colder weather.

Here is the packed bag just before closing.

I will be traveling for 2 weeks in the fall and I will share how I will be packing for that trip as the time gets closer.

What is your packing plan when you travel? I’d love to hear all about it in the comments.

– xG