Vacation outfits don’t come naturally to me. The demanding schedule and constant climate adaptations that come with traveling means packing for a vacation will often clash with my desire to put on looks that are fashionable, but impractical. After years of over-packing and putting my feet through the pain of wearing inappropriate shoes for hours-long sightseeing trips, I finally got down to perfecting a capsule wardrobe for joyous travel.
Ahead of a seven-day trip to Portugal, where I’d be in temperatures ranging from 40 to 65 degrees and would visit both historical places and natural landscapes, it seemed like the right moment to refine both my packing and styling strategies.
Thankfully, there was a time when all I did was pack for days-long trips and had to adapt my style to match this lifestyle. Back in 2015, when I studied abroad in Spain, my weekends consisted of hours-long travel — whether via bus, train, or plane — where I’d have to carry all my belongings in a tiny carry-on suitcase or backpack (RyanAir’s bag restrictions are enough to induce PTSD). At the time, I figured my best strategy was to wear neutral colors, pack shoes that could withstand any terrain, and pick pieces that were both versatile and chic. I pride myself in having packed for both cold and warm weather on a two-week trip through Europe — with styles ranging from beachy jumpsuits to a felt wide-brim hat — in a carry-on suitcase so small it might as well have been a backpack.
Though years had passed and I was no longer a city-hopping student, I figured my best bet to enjoy my time in Portugal was to look to that era for inspiration. The strategy was simple. I packed two T-shirts (black and white, of course), one long-sleeved shirt, one pair of wide-leg pants, two jackets (one denim and one leather), and a pair of dark wash jeans. I also brought two blazers for warmer days, as well as accessories that would enhance the otherwise boring outfits, including a velvet hair bow. For shoes, sneakers were my go-tos, bringing with me one pair for long walking days in nature settings and another for city adventures.
And it worked. As I reviewed the trip’s outfits, it’s clear they all look very similar. And that’s by design. Why waste precious energy in decision fatigue during a vacation? Here are all the ways I perfected my traveling capsule wardrobe.
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Airport To Sightsee Look
A seven-hour flight is never a pleasant experience. So, dressing for one is a nightmare. Still, this time around I settled for a simple T-shirt and joggers that I later styled with a dark denim jacket and sunglasses as I stepped off the plane straight to sightseeing.
Chic Sightseeing Outfit
When faced with a day of walking around 19th century palaces in Portugal, a velvet bow was the best accessory to dress like a real life storybook character. Still, I was a tourist first, which made me keep my outfit simple, pairing a brown blazer with dark denim and sneakers.
The Train Ride Outfit
Remember what I said about seven-hour flights? Well, three-hour train rides are no walk in the park either. This is why I decided to wear the same black joggers, only this time I styled it with a long-sleeve striped shirt and leather jacket for an edgier look.
The Tourist-Core Outfit
Airport dads were the main inspiration for this outfit, which I’m dubbing “tourist-core.” For a day of exploring in Cascais, Portugal, I chose to wear the long-sleeved shirt from the previous outfit with dark wash denim and a black blazer. For additional styling (and warmth!) I wore a gray sweater over my shoulders, which I promptly put on as the day’s temperature dropped.