What I packed for two months in Portugal

This is my general go-to Winter packing list for a long trip. I usually pack half of what is on this list for a week back East during colder months.

We just got back from spending two months in Portugal, and one of the most common questions I got was:
“How did you decide what to pack for such a long trip?”

We were there through the end of winter and into the beginning of spring. The climate reminded us a lot of the Bay Area—mild, changeable, and sometimes rainy—so layers were key. We wanted to look a bit more stylish day-to-day, so we ditched the big puffy jackets (you know the ones Americans are famous for) in favor of lightweight outerwear and raincoats. That turned out to be perfect—it rained a lot!

As the trip went on, the weather warmed up. By the time we left, the 70s had arrived and started to tease us with the feeling of early summer. We were able to shed some layers and still feel put together. I can confidently say we nailed our packing strategy. Lenny did great too—he packed a similar wardrobe, just with a few more button-downs and fewer sweaters. If you're interested in what he brings, let me know—I'm happy to put together a "his list" for next time.

I packed everything into a 21” suitcase (the kind that can be carried on or checked). We chose to check ours this time since we also had carry-ons as well as camera gear. I don’t use packing cubes (Lenny does)—I rely on the old roll-and-tuck method. I stuff socks into shoes and boots, and used my carry-on (my new favorite, the ReNew Transit Bag) for t-shirts and fragile souvenirs like Portuguese ceramics.

Be warned - I am all about Black and White. That's a solid travel philosophy—black and white is timeless, versatile, and effortlessly chic. I can layer, mix textures, or add a bold accessory (like a scarf) if I ever want to switch it up, but otherwise it’s a no-fail palette that works in any setting from day to night.

Here’s What I Packed (In Addition to the Usual Travel Essentials):

Bottoms

• 2 pairs of blue jeans (wore the heavier wide-legged ones on the plane)

• 1 pair black corduroy jeans

• 1 pair lightweight chinos (Target find—now own them in every color!)

• 1 pair white wide-legged jeans

• 1 long black silk skirt (great with sneakers, sandals, or layered up)

Tops

• 1 long-sleeved black t-shirt (my travel shirt)

• 1 washable black silk shirt (wrinkle-resistant MVP)

• 3 white short-sleeved t-shirts

• 3 black short-sleeved t-shirts

• 1 ecru short-sleeved t-shirt (cute with white jeans)

• 2 white tank tops (layering)

• 2 black tank tops (layering)

Sweaters

• 1 black v-neck cashmere sweater

• 1 black crew neck cashmere sweater

• 1 grey lightweight wool-blend crew neck sweater

• 1 black cashmere cardigan

Other Clothing

• 1 swimsuit (always bring one—you never know!)

• 1 swimsuit cover-up

• 1 rain jacket

• 1 lightweight cotton jacket (wore on the plane)

• 2 nightgowns

• 1 pair yoga pants

• 1 yoga bra top

Undergarments

• 7 pairs of underwear

• 4 bras (2 beige, 2 black)

• 2 pairs boot socks

• 2 pairs low-cut sneaker socks

Shoes

• 1 pair black Converse sneakers

• 1 pair black Allbirds sneakers

• 1 pair Sezane dress boots (didn’t end up wearing—weather)

• 1 pair espadrilles (ditto—too rainy)

• 1 pair Chelsea boots (wore them flying—bulky but super comfortable)

Extras

• 2 travel books (came home with two more—still fit in the suitcase!)

What I’d Do Differently:

Honestly, not much. We had a washer in our apartment and did laundry weekly, so the capsule wardrobe approach worked beautifully.

Next time, if it’s still winter, I’d leave the dress boots and espadrilles behind—I didn’t wear them once.

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What Do You Pack for a Long Trip?
I love hearing other people’s packing strategies and space-saving tricks. Let’s swap notes!