Mistakes I Made When Packing for My Long-Term Trip

Open red leather purse with empty interior ready for packing

Like many women, I worried about what to pack for my trip. Unfortunately, I had a health scare and inadvertently lost fifteen pounds, and now items in my closet run too big.

This unexpected weight loss not only changed my body. It forced me to rethink my entire wardrobe for the trip. Down two dress sizes, I bought a casual yet chic wardrobe to lug with me.

Everyone online had a packing strategy, primarily based on their own body shape and fashion sense. Everyone warned that you can easily overstuff your suitcase.

Here’s what made it into my luggage.

I ended up packing eight shirts (all short-sleeved), a skirt, a jumpsuit, three dresses, two sweaters, and two pairs of pants. From my closet, I pulled out two pairs of jeans and my favorite red blazer, which still fit.

I stuffed twenty clothing items in my luggage, defying online recommendations. As advised, the mostly neutral colors (white, beige, navy, and black) and the absence of prints made mixing and matching easier. Four packing cubes helped me squeeze these items into my carry-on and suitcase.

Two navy blue suitcases, a blue travel backpack, and a cross-body purse on a cream-colored floor, ready for long-term travel.
Rolling through life with my entire wardrobe.


I appreciated the online tips about how much underwear to carry. Most people said three bras and eight to ten pairs of panties would hold me for three months. I agree.

The women’s advice on footwear was unanimous. Bring only three pairs. Still, I managed to fit seven pairs of shoes into my 28-inch suitcase.

I packed sneakers, slippers, Mary Jane flats, low-heeled sandals, high-heeled sandals, and two pairs of flip-flops.

My rationale was simple: three months is a substantial period, and being prepared, especially with my size 5.5 feet, was a wise move.

Black shoes, white and beige sneakers neatly arranged on a wooden table, showcasing a minimalist travel wardrobe.
Three pairs of shoes that made it into my suitcase.

How I packed from the heart, not the head.

When I packed, I envisioned every scenario, as if I were in a movie. What if I attended a soirée in Athens? Maybe then I would have needed the black heels that I have worn only once.

I learned two other lessons about packing shoes. Firstly, break them in before walking on the lovely but brutal cobblestone streets in Europe. My sneakers took a week to soften, but they became my uniform.

Secondly, consider the shoe materials, no matter how cute the shoe is. The sullied suede parts of my sneakers ruined the shoes. Unfortunately, the shoe cleaner I bought in Rome couldn’t save them. I tossed my beloved sneakers in a trash can at a four-star hotel in Vienna, Austria.

My packing mistakes added up.

I spent hours searching for a new pair of sneakers at a mall in Cascais, Portugal. This venture cost me time and $143.

Initially, I skirted weight restrictions at airports. However, as I picked up a few clothing items and hair products in Europe, the weight of my suitcase began to weigh me down.

I paid $59 to check my suitcase on a flight out of Chania, Greece. To accommodate the growing size of my belongings, I bought a purple silicon carry-on for $33 from a market vendor in Kuşadası, Turkey. When I managed to downsize my possessions, I gifted the carry-on to a kind hotel worker in Barcelona, Spain.

My original packing strategy had failed me. The weight of my luggage slowed down my movements and my ability to fully enjoy the trip.

Close-up of a white washing machine dial with Greek labels, showing settings on a clean surface.
I ruined a precious sweater after misreading a Greek washing machine label.

My plans changed. My suitcase didn’t.

Now that I have extended my travels, I dread the upcoming changing of the seasons. In late August, in Barcelona, I found a post office and sent most of my summer dresses back to the States before realizing I would be heading to Costa Rica several weeks later.

The total cost to mail this package was $78. However, I won’t be in warmer climates the entirety of this trip. What happens then? I bought a few long-sleeve shirts and lightweight sweaters, but I don’t have a winter coat or gloves.

My all-seeing camera caught my packing mistake.

Before I knew I would launch a travel blog, I didn’t consider whether my outfits were photogenic. In person, a beige linen dress looked stylish. In photos, it resembled a knapsack.

My polo shirt shone like polyester from the 1970s. My navy blouse drooped after improperly hanging on a hotel hanger.

The one item that stood out (enough) was the denim dress that I found in a TJ Maxx store. Coincidentally, I have worn the dress several times for pictures.

A friend texted me, “You need new clothes.”

Wooden wardrobe with a navy dress, cream pants, and a jean dress hanging, creating a minimalist travel wardrobe on a cream floor.
This jean dress became my go-to for both comfort and style.

Overpacking taught me what truly matters.

On my next trip, if there is one, I will do better. I have learned valuable lessons about packing and dressing for long-term travel. I will take pictures of myself in clothes while at stores. I will buy more seasonal items.

If I ever travel the world again, I want to feel the same way I do now. I have enjoyed exploring iconic cities, such as Florence, Italy, and lesser-known towns, such as Agios Nikolas, Greece.

On the plane to Greece, I met a twentysomething man named Kosta. During the flight, we formed a friendship, bonding over our shared love of history and travel.

He spent a month, crisscrossing Greece, touring his parents’ homeland. As long-term travelers, we have discussed the concept of permanence, which can be fleeting. I struggle with relying on items in my luggage to meet all my needs.

Still, long-term travel requires compromise. My fond memories of this trip will last longer than the popularity or weight of my clothes.