What to Wear in Lisbon in Autumn – Carry On Only!

In Autumn 2015, my boyfriend and I decided to take a break from our lives in Canada and go live in Madrid, Spain for a year while exploring other parts of the continent.

Our European adventure started off in Portugal. It was early-October and we were looking for a vacation destination that would let us cling to summer and ease into fall, and Lisbon did just that. Daytime temperatures rarely dipped below 20C and, other than one day where the skies opened upon us, we basked in glorious sunshine while we explore the city of seven hills.

It was perfect!

What made it even more perfect was that during our time in Lisbon, I was able to hone the ideal travel wardrobe, one that could conveniently fit in a piece of carry-on.

To ensure you have the perfect early-autumn getaway to Lisbon, pack these six pieces in your carry-on. 

Comfortable Flats

When they say Lisbon is a city of hills, they really aren’t joking. The city is situated on seven hills – that’s right SEVEN – and at times, it seems no matter where you’re headed, you’re bound to be walking up a hill. This means that comfortable shoes are a must.

I honestly don’t know what I’d have done if I didn’t have my beloved Crocs flats with me. They helped me scale the hills, steps, and slopes no matter the terrain. They also kept me comfortable as we tried (and failed) to navigate the cobblestone alleyways of the Alfama neighborhood.

My crocs were also the perfect footwear for the unpredictable weather I encountered in Lisbon. Throughout my time in the city, I had glorious sunshine, scorching heat and torrential downpours. No matter what Mother Nature threw at me, I knew my crocs could handle it.

A Few of Our Other Favorites:

Lightweight Pants and Shorts

Temperatures were hot in Lisbon in October (at least compared to what we’re used to in Canada), which meant I could happily run around the city in a pair of lightweight shorts during the day.

On those days where I needed a break from the sun or if we had plans to be out near the water, I’d swap out my shorts for a pair of classic linen pants – easy, breezy, comfortable and oh so perfect when wandering through the Portuguese capital.

A Few of Our Favorites:


I like to keep it simple when I travel, which is why I relied heavily on basic black t-shirts when in Lisbon. Not only did the classic black tee go with everything, but they were the perfect piece to layer under a cardigan when temperatures started to dip in the evening.

Maxi dresses

After a long day of intense exploring, it can be hard to find the energy to get dolled up for a night on the town. This is why I loved slipping into a maxi dress. Not only did I instantly feel put together but I didn’t have to worry about packing matching tops and bottoms. Throw on a cardi, or drape a scarf over my shoulders and I was ready for a night of delicious food and wine.

A Few of Our Favorites:


Another classic wardrobe staple, cardigans are the perfect item to top off any look. I’d throw one over my shoulders when I need a quick break from the sun, or slip one on over a dress, allowing me to comfortably sit out for a night of stargazing and sipping wine on one of Lisbon’s many terraces.

A Few of Our Favorites:


And last, but certainly not least, when packing for a Lisbon city break (or any city break for that matter), I tuck a lightweight scarf in my bag. Not only did this come in handy on the plane, but much like the cardigan, I often used it as another layer to stay warm or protect my arms from the sun while out sightseeing. Additionally, I find that scarves are one of the easiest ways to inject a little color, pattern or both into my clean and classic traveler ensemble.

There you have it, the six key pieces you need to pack in your hand luggage to ensure you have a fashionable and fabulous early-Autumn vacation in Lisbon.

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Kate Slean is a wanderluster, fashion fiend, and list-maker extraordinaire. Originally from Canada, Kate is currently based in Europe, traveling as much as possible. When she’s not exploring the world, Kate is on the hunt for the latest and greatest trends in petite fashion. At just 5’2″ Kate knows just how hard it can be to find the perfect fit, style, trend, and she wants to help others avoid the struggle. Kate enjoys writing about her everyday experiences of dressing as a petite, and the never-ending quest to find the perfect petite pencil skirt. You can stay up-to-date on all Kate’s adventures on her blog, Petite Adventures.

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