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Shoulda Woulda Coulda: My Biggest Packing Mistake

Comfortable and confident in Thailand

By Brenna Holeman

“Are you sure you don’t want any of this stuff?” The German girls looked at me inquisitively. I had just handed over more than half of my backpack to them in our shared hostel room in Budapest.

“No,” I said. “Take it all.”

That was in 2006, on my first big backpacking adventure around Europe. I had just graduated university in Canada, and in planning for my trip abroad I consulted countless guidebooks. There were very few websites on packing at the time, and I certainly could have used the help from a site like this one.

There's a reason all my photos are from the waist-up when I first arrived in Europe
There’s a reason all my photos are from the waist-up when I first arrived in Europe.

Overwhelmed by generic and non-gender-specific packing lists and underwhelmed by the choices of hiking boots, I filled my bag with all the wrong things. I packed for a very outdoorsy, adventure-filled holiday, even though I sensed my time in Europe would be spent mostly in cathedrals and cafés. Worse than that, I packed clothes I didn’t feel very good in: unflattering pants, drab t-shirts, and only one skirt. As someone who wears skirts or dresses 364 days of the year, I didn’t pack effectively at all. In fact, I packed for somebody else, some vision of a backpacker I had in my mind. I went to the nearest store with a travel section and grabbed things to check off my list, without stopping to think if I actually wanted to wear them or if they fit me very well.

When I got on the plane to Amsterdam, I wasn’t myself. I had taken the backpacker image to the extreme, imagining I had to have a different style. I felt frumpy and uncomfortable. That summer, I predictably ended up ditching the clothes I hated and purchasing a new wardrobe in Prague. I bought practical travel clothes, but clothes I also felt confident in, clothes that suited my personality as well as my traveling lifestyle. I even gave away the expensive hiking boots I had brought with me, trading them in for comfortable runners more suitable for city sightseeing. As a bonus, my backpack was lighter and I had more room for souvenirs. Feeling more confident, I’m sure I also blended in to the local culture better.

Feeling much more like myself in Dublin
Feeling much more like myself in Dublin.

In the past few years, on backpacking trips through Asia and South America, I took my time to plan the perfect wardrobe. I researched thoroughly, and packed for the kinds of trips I was taking. I still rarely wear pants or jeans, so I adapted my backpack to include harem pants and leggings; I layer the leggings under shorts while hiking, or under maxi skirts for warmth.

Comfortable and confident in Thailand
Comfortable and confident in Thailand.

As I wear mostly skirts and dresses at home, I pack accordingly, always including a few of each in varying lengths. I also purchase scarves or cheap jewelry when I get a bit bored of my wardrobe, as it’s amazing how these little things can jazz up an outfit. Nobody should have to change their style when they travel, but it’s all about adapting in order to create a wardrobe that’s both functional and fun. And as all travelers know, the ability to adapt is crucial.

Adapting my wardrobe to be both practical and personal in Nepal
Adapting my wardrobe to be both practical and personal in Nepal.

The biggest mistake I made in packing for that trip in 2006 was not packing for myself. Through my own mistakes and through reading sites like this one, I learned that the key to packing successfully is to bring the necessities, but to make sure the necessities fit my style. I want the clothes to be practical, of course, but I also want to feel confident and comfortable. Now, when packing, I always make sure to bring things that I would wear whether or not I was travelling. It may seem obvious, but it took a few months of feeling very insecure in my travel clothes to figure that out.

Brenna in BurmaAbout the Author: Brenna Holeman has been travelling solo for over seven years, visiting all of the continents but one (guess which one?). She is moving to London in the autumn to start a Master’s degree in Creative Non-Fiction Writing. She loves red wine, scuba diving, and window seats. Follow her on her blog, This Battered Suitcase, or on Facebook or Twitter.

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Reader Interactions


  1. Alyssa says

    It’s great to get advice on packing from such a seasoned traveller. Plus, I love your style! I only dream of pulling off boho chic that way.

    I always try to bring stuff from my own wardrobe when packing for trips instead of shop. I also consider that if I don’t do it at home, then I probably won’t do it abroad.

    Brenna circa 2006 – o0oh gurl, dat hurr 😛

    Yours in Travel,


  2. Nurse-issistic Traveller says

    Very true. I’ve made this mistake too. It’s like trying to play a role. Trying to be someone I’m not. Trying to look like a hardcore backpacker or even trying to wear what locals do just so we can blend in. In the end, I realized that there’s no dress code when travelling and that the best way to belong on the road is to be yourself. Now, I pack for comfort and functionality rather than style.

  3. Sofie says

    On my last trip (to Portugal) I mainly packed dresses and skirts for the first time.
    Such an improvement! They take up way less space than pants or shorts and you only need one item of clothing to cover yourself up.
    I also took tights to wear under them for warmth.

  4. Carolyn says

    I had a very similar experience on my first trip to Europe. I packed horrible, frumpy things and I still feel some discomfort when I look at those pictures, AND I stood out horribly from the chic European women. I would have loved advice like this back then.

  5. Laryssa says

    Loved this post! It’s so true and I’ve made the same mistakes. It also explains why so many people wander around in Hawaiian shirts on cruises I feel — it’s what they think they SHOULD be wearing.

  6. Sonja says

    I think this might be one of my favourite articles on this blog … After reading through to most of its pages by now, I started to feel plagued by inklings of inadequacy – I thought I would have to buy so much stuff that’s recommended here if I want to travel more and more efficiently. After reading your contribution, I’ve breathed a sigh of relief and decided to focus more on myself and my necessities. That’s both the beauty and the danger of the internet – so many possibilities can open worlds to us but also create self-imposed pressure.

  7. MacKensie says

    Great article! Feeling frumpy and not yourself is a real bummer when you’re traveling. Like another commenter said, it’s like you’re taking on a role- but you don’t have to do it!


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