I Packed for 5 Trips in One Suitcase—20 Versatile Items I Wore in Every Place

October was simultaneously one of the best and most exhausting months of my entire life. It started with 10 days in Italy and Switzerland, where I traveled with my single carry-on suitcase from Ligurian Sea towns to Milan to Lake Lugano. It was 80° by the water, calling for bikinis, cover-ups, and billowy skirts and dresses. Meanwhile, in the cities, I needed lightweight outerwear for the chilly early mornings and evenings spent café and restaurant hopping as well as comfortable walking shoes that still fit in with the chic nature of my surroundings. Packing everything for the dueling settings was a bit like playing Tetris with the limited amount of space I had in my suitcase. Plus, I needed room for shopping. 

A handful of days after I returned home to New York, I left again for a week—first to Chicago, where it was already pretty much winter, and then to Austin, where it neared 100° every day. Somehow, I managed to keep most of the contents of my Italy suitcase intact, only switching out the swimsuits for two coats and adding a few Western pieces to fit the local Texan aesthetic. 

In total, I hit five locations, from Austin to Lugano, with pretty much the exact same items, give or take a few. Below, see which pieces worked for them all, despite the changing weather, occasions, and dress codes. 

I very rarely fly anywhere without a pair of 501s. That's practically a rule in my household. After all, they can so easily be dressed up and down and are comfortable enough to fly in. Mine are vintage, but the new pair below is just as good, especially after they've been worn a few dozen times. In both Milan and Austin, I paired them with a semi-sheer white button-down shirt from Me+Em that's been a staple in my wardrobe ever since I got it last year. I always add a belt to the combo, usually a black-and-gold one from J.Crew, but sometimes, I change it up and accessorize with kitten-heel mules and my Bottega Veneta Andiamo bag, one of two bags that came with me to all five locations. 

For the Grand Prix in Austin, my plan was to really play into the Western aesthetic that's been buzzing around the fashion world of late. Therefore, when I stopped home in between vacations, I threw in these lizard-print mules and my cream-colored cowboy hat from Cafe Society. Otherwise, I pretty much copied and pasted my packed items from Italy. 

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I got this voluminous white cotton skirt this summer and haven't run out of ways to wear it yet. It's dressy enough that I can style it for the nicest of restaurants in Milan with some heels and a simple black top. Meanwhile, when I throw it on with a bikini and ballet flats, it's perfect for the rocky beaches on the Ligurian Sea. 

But I didn't stop there. When I headed to Austin a few weeks later, it made for a stellar Western look when paired with a black fitted vest and cowboy boots. The possibilities really are endless. 

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Call it my Chicago roots, but I never go anywhere without some form of outerwear, no matter what the predicted weather is. Usually, I'm leaving from somewhere slightly chillier, so I wear it on the plane. For this round of travel, I brought along my new Toteme scarf-coat. 

The editor-favorite coat ended up being the perfect blanket alternative on my overnight flight to Milan as well as a great Western touch in Austin and protector from the wind in Chicago. 

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I've been on far too many trips when I've wanted to go somewhere nicer, usually a restaurant, and not had a dress nice enough to wear to it. Now, I always pack something semiformal that rolls up nicely and doesn't take up too much space just in case I want to dress up for something. This time around, I went with a high-neck LBD from Bernadette, which is made of lightweight but crisp taffeta that doesn't wrinkle ever. 

I wore it to Fondazione Prada, the Prada museum in Milan, with a green COS sweater to dress it down. I then rewore it in Chicago for dinner with friends and again in Austin when we ate at Driskill Grill after the sprint race. It's one of the oldest restaurants in Austin and has a really cool, elegant energy inside, so I thought I'd dress for the occasion. 

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The same Me+Em button-down made multiple appearances around Italy, but instead of with jeans, I paired it with these sand-colored COS trousers that are loose and low-rise, making them perfect for train and plane travel, which we did a lot of on this journey. With this outfit, I wore it unbuttoned with some type of tank, usually my go-to Madewell Brightside Tank, and the same belt, shoes, and bag as the jeans look. 

These trousers are selling out quickly, but if your size is still available, snatch up a pair ASAP. They don't wrinkle at all and are beyond comfortable. If you're like me and don't like to travel in sweatpants or anything overly casual, these are the ideal bottoms for you. 

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I bought this Tory Burch tunic when it went on sale ahead of the brand's New York Fashion Week show to wear to the event, and the day before the show, I went back for the matching skirt. Little did I know the set would be perfect as separates on my Italy trip, where I wore the tunic alone with a trench coat to shop around Milan and the skirt with a Dissh halter top for a day trip to Portofino from Camogli. 

I thought the tunic was the star of the show, and in some ways, it is, but this skirt is just as great on its own. It features subtle red and blue stripes on the oat-colored fabric and a high slit on one side. As a bonus, it rolls up well for compact packing and unrolls without any sign that it spent hours inside my suitcase. 

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