Milan Is Peak Luxury—Here’s Everything I Packed to Look Like a Local

Close your eyes and picture the perfect vacation—where are you? For me, there’s no denying the allure of one destination: Milan, Italy. Often referred to as one of the economic hubs of Italy, the city on the surface may seem less exciting compared to the more “Instagram-friendly” cities in the south—e.g., Positano, Florence, or Rome. However, I’d argue that there’s so much to love about this metropolis that meets the eye, or at least that’s the opinion I’ve formed after spending four days exploring the destination on a press trip. From endless art galleries to some of the world’s best restaurants, there’s no shortage of incredible things Milan has to offer.

But possibly the best thing about this destination isn’t necessarily its touristy sites but rather its creative community. After all, Milan is renowned as the world’s design capital—hello, it hosts one of the biggest fashion weeks! But beyond big luxury houses, there’s a wave of smaller brands pushing the boundaries of design in new ways. Surprisingly, one of those brands is OtterBox. (Yes, I’m talking about the tech accessory brand.) While it was founded in Fort Collins, Colorado, it recently partnered with Desserto, a Milan-based sustainable textile producer, to create a collection of cactus-leather phone cases. It’s one of those collaborations that seem unconventional yet capture so much of the innovation that’s a central part of Milanese culture.

Plus, if we’re being honest, we’re in an era when the tech accessories you pack for a trip are just as essential (if not more so) as the clothes you choose to wear—especially if you’re planning on having the most TikTok-worthy trip in Italy. Therefore, when I got the opportunity to travel to Milan to learn more about OtterBox, I said, “Andiamo.” Ahead, I’m sharing a full breakdown of everything I packed (from purses to phone chargers) for the trip with OtterBox to Milan, along with a comprehensive itinerary of where we stayed and what we ate, shopped, and did—just in case you feel inspired to book your own trip.

Day 1

Confession: I’m pretty picky when it comes to traveling. I’m meticulous about planning every aspect of the trip, from picking the hotel to creating a PowerPoint for what to pack. Admittedly, I was a bit nervous about going on a press trip, but the moment I landed in Milan, I was immediately impressed by OtterBox and its press team’s planning. Not only did they arrange for a driver to pick me up from the airport—side note: It’s worth arranging a driver over taking the train because it can be overwhelming to navigate after a long flight—but the hotel, Aethos Milan, was perfection. Nestled in the city center, the boutique hotel boasts 32 rooms, each with its own theme (mine happened to be sports-centric), making it unique.

On top of the eccentric design, unlike other hotels in Europe with little communal space, Aethos has ample room to hang out with locals and travelers, which sets it apart. The hotel has a chic little café, a restaurant, and even a buzzy nightlife venue attached called Doping Bar (which was quite popping at night, BTW). The hotel’s prime location in the city, paired with its playful interiors, passed my picky expectations with flying colors from the jump. It was such a comfortable place to stay that upon my arrival, I found myself quickly relaxing. I decided to rest for a bit by doing a little post-flight skincare routine, charging my phone (with my OtterBox adapter, obviously), and taking a quick nap. After feeling rejuvenated, I decided to steam my ensemble, spritz my signature perfume, and set out to explore the surrounding area before my evening plans with the OtterBox team.

WEARING: Prada Symbole Sunglasses ($517); vintage earrings and blazer; Aritzia skirt; Steve Madden Dreaming Flats ($90)

Although I’d visited Milan twice before, I’d never realized that the city was built with a series of water canals, not dissimilar to those in Venice. That fact became apparent quickly, as the waterways were right by the hotel. The neighborhood, often referred to as the Navigli District, is quite charming. All the canals are surrounded by a series of small shops and tiny trattorias that don’t feel as tourist-trappy as those in other parts of town. It’s a great area to meander without making formal plans. I’d recommend wearing something comfortable but chic to fit in with the crowd.

I wanted to wear something that leaned a bit more classic for my walk, so I opted for an all-black ensemble with a few contemporary touches. I styled my vintage nipped-waist black blazer with a now-sold-out satin balloon skirt from Aritzia, mesh ballet flats from Steve Madden, vintage clip-on earrings, a stretchy headband, and a pistachio-green shoulder bag from Freja New York. What I loved about this look was that it felt more aligned with the formality we see on the Milanese fashion scene, but it was still comfortable enough to meander through the streets on a semi-cloudy day. Plus, I typically try to keep the first outfit on a trip a bit more “boring” because there’s nothing worse than feeling uncomfortable after a long flight.

After I walked around the neighborhood, I headed back to the hotel to freshen up for drinks and dinner with the OtterBox team. Rather than changing my entire outfit again, I decided to swap out my shoes for a pair of embellished ballet flats from Steve Madden that would give the ensemble an evening feel while being comfortable enough to walk to our dinner reservation. Admittedly, I was nervous about what the group of fellow travelers would be like, but upon meeting to grab an aperitif in the hotel’s bar, we immediately bonded over the fact we were all wearing ballet flats from Steve Madden. (It wasn’t planned.)

Those flats came in handy because we walked for about 15 minutes to our dinner spot for the evening, Langosteria Bistrot. The fine-dining restaurant is known for its seafood, which was delicious, for the record, but I was most blown away by the tea that the waiter spilled: Rihanna had eaten there a few weeks prior. Although they wouldn’t dish on what she ordered, after trying a few things on the menu, I’d say that the red tuna tartare and calamarata pasta were the highlights of the meal—everyone at the table took out their phones to take pictures of the dishes. It was the ideal dinner to kick off the trip.

Day 2

Following a successful first evening in Milan, I didn’t think it could get much better, but my second day started off at the spa. OtterBox booked us an appointment at one of the city’s top-rated wellness centers: QC Termemilano. First off, I have to say that it’s unlike any other spa I’ve ever had the privilege of seeing. Upon stepping in from the bustling streets of Milan, you’re met with an environment that’s enveloping to the senses. Every aspect of the space itself is thought out impeccably—from the bright entryway featuring high ceilings and mosaic tile floors to the Italian-themed rooms throughout the spa. It was particularly the latter that impressed me, as before my massage, we meandered through each of the rooms, which featured everything from scenic saunas to hot springs and even rain rooms.

The spa was so stunning that I was grateful I chose to wear a more fashion-forward swimsuit for the morning. I packed my pretty one-piece suit from Same Los Angeles. It wasn’t planned, but it serendipitously ended up matching my favorite room in the spa, the sauna, entitled Roseto Gran Milan, which was covered in hand-painted roses that are native to Milan. Since the rosette bust of my suit matched the vibe of the room, I had to take out my phone to snap a picture. Honestly, at that moment, I was thankful that my OtterBox case protected my phone while I proceeded to do a photo shoot in this particularly hot room, as it could have been a whole disaster. After getting the ‘gram, I headed to my massage, which was arguably one of the best I’ve had in my life. Despite being only 25 minutes, the massage made me weep on the table (in a good way). It was the perfect way to start a morning in Milan, no doubt.

WEARING: OtterBox Symmetry Series Clear Case ($40); Tory Burch Earrings; Tove Ceres Dress in Blue; Jenny Bird Ola Gold Bangle ($248) and Silver Bangle ($248); Freja New York Caroline Bag ($258)

Feeling fully relaxed, I was able to then focus on the purpose of my Milan trip: to learn about the launch of OtterBox’s newest collection. Knowing I’d spend much of the afternoon at a showroom, I wore a straightforward look. I landed on this incredible dress from Tove, which is now sold out, but I managed to find it on The RealReal. Since the dress itself is quite minimalist besides the bright-cobalt shade, I decided to let the accessories be the focus of the look by stacking on the jewelry—specifically my favorite hoops from Tory Burch’s S/S 23 collection and a few stacked bangles from Jenny Bird. The look was the perfect choice for the day, as it allowed me to spend the afternoon learning about OtterBox’s newest collection without thinking about potential fashion mishaps.

Until this trip, I didn’t know much about the history of OtterBox. However, I learned that while the brand started by making element-proof boxes to protect outdoorsy people’s electronics, it’s expanded way beyond that in the last 26 years. The brand has become beloved among everyone from the tech-obsessed to the outdoorsy because it offers endurance-tested phone cases, power devices, and other accessories. While most might not necessarily think of this brand as a fashion brand, by all accounts, it’s begun to branch into the territory. That’s most apparent in the recent collaboration with the sustainable textile producer Desserto. Understanding that the fashion and tech industries have the largest impact on the environment on a global scale, OtterBox set out to create a collection of phone cases that addressed those issues, and its Symmetry Series Cactus Leather Cases do just that.

While in Desserto’s Milan showroom, I learned that cactus leather is the most sustainable material during production because, unlike other textiles, cacti require the least amount of water and don’t damage the agricultural landscape like other crops. Plus, making the material requires less water and energy. On top of that, the brands worked together for years to develop a version of the leather that would live up to the durability associated with OtterBox’s tech accessories. So every aspect of these cases is designed to be sustainable in the long haul. Overall, I found it incredibly fascinating to learn how these cases came to fruition; it made me appreciate how things are made. But that sentiment was even further emphasized when OtterBox arranged for a local jewelry maker (behind the brand PLV Milano) to teach us how to make our own beaded pieces. We spent a few hours crafting our own necklaces, belly chains, and phone charms, all with cactus leather string. It was indeed an informative afternoon.

After the showroom, I returned to the hotel to change for the evening. Arguably our itinerary for this second evening was the swankiest, as we were taking a cocktail-making class at the historic bar Camparino in Galleria. Situated across from the Duomo inside the Galleria Vittorio Emanuele II, the saloon is not only one of the most famous in the world, but it’s beloved among the Milanese for its history (and happy hour). It’s referred to as the birthplace of Milano’s spirit of choice, Campari, because it was first served in that very spot in 1915. The bar is quite beautiful, as it boasts lofty ceilings covered in hand-painted mosaics, antique chandeliers, and an old wooden standing bar.

However, what draws a crowd isn’t the chic interiors so much as the cocktails—a fact that became apparent to me when we headed upstairs to the second floor, which houses the spot’s swanky restaurant extension. Compared to the vibe downstairs (aka the Bar di Passo), the upstairs is far more contemporary, with pops of red velvet on bar stools, pop art, and good music bumping in the background. Upstairs, or what’s referred to as Sala Spiritello, was the perfect place to have an entire masterclass on how to craft cocktails—all of which we gleefully recorded with our hands glued to the outside edges of our OtterBox cases. After a successful lesson, I can safely say that whether you don’t drink often (like me) or are a craft cocktail connoisseur, visiting Camparino in Galleria is a nonnegotiable for any trip to Milan.

Even if you don’t like to drink, everyone has to eat. Luckily, Camparino has you covered for that too. After our aperitivo masterclass, we sat down at our table, which was situated in the back corner against a wall of Campari bottles—it was a vibe, to say the least. Our courses were just as good as the craft cocktails, as there was a great mix of delicious options, including the tartare and cannelloni pasta. But the one dish I’ll spend the rest of my life thinking about was the tiramisu; it was heavenly. I also should note that the restaurant is a spot to be seen—we caught wind of a rumor that before we showed up, royalty had been casually hanging out upstairs, so you know it’s cool. Overall, if you can snag a reservation, you’ll undoubtedly have one of the most luxurious dinners of your life at Camparino. (I know I did.)

WEARING: Jenny Bird Nouveaux Puff Earrings ($138); Haus Labs by Lady Gaga PhD Hybrid Lip Glaze Plumping Gloss ($26); Bottega Veneta Fluid Metal Dress; Sonia Rykiel Domino Vinyl Mini Bag; Khaite Seneca Wedges

Last, I’d be remiss if I didn’t mention what I wore for the evening, because the beautiful space inspired me to do a full photo shoot (naturally). If there’s any place to get all dressed up for a dinner in Milan, it’s Camparino, hands down. Because I knew that going into the evening, I landed on wearing my Bottega Veneta burgundy suede dress. The moment I spotted this dress in Matthieu Blazy’s S/S 23 show, I was obsessed, but I never thought I’d be able to own it until I found it on The RealReal. Because it was such an incredible find, I knew I had to pack it for this trip, but I wanted to ensure the styling allowed the piece to shine. I landed on keeping the rest of my look minimal by pairing it with gold sculptural earrings from Jenny Bird, a black crescent mini bag from Sonia Rykiel, strappy wedge sandals from Khaite, and a swipe of red lip gloss. My only regret for the evening was that I didn’t have a matching phone case from OtterBox to go with the look. Nevertheless, it was an incredibly stylish evening.

Day 3

At this point, I didn’t think that this trip could get even better, but day three proved me wrong. For the day, OtterBox organized a day trip from Milan to Lake Como, which, for the record, is about an hour’s drive from the center of the city. It’s a relatively easy place to plan a day excursion to. I’d recommend packing appropriately for the day. Since I knew we’d be taking boats around Lake Como, I made sure that I brought along my OtterBox portable charger to take pictures throughout the day, along with light layers, snacks, and sunscreen. That being said, logistically, there are so many tours you can book in the region, but I recommend the boat tour we took with Vaporina. We all got to ride around Lake Como in idyllic wooden boats as our tour guide told us about the area’s history, showed us celebrity houses, and made various stops throughout the day. As someone who’s gone on her fair share of travel tours, this was one of the best experiences I’ve ever had.

WEARING: Jenny Bird Chunky Doune Hoops ($138); Prada Symbole Sunglasses ($517); Reformation Malika Linen Top ($148); Free People Emilia Full Skirt ($98); Freja New York Mini Chrystie Pistachio Bag ($268); Steve Madden Dreaming Mesh Mary Janes ($90); Sézane Gaspard Cardigan ($120)

As mentioned before, when taking a day trip to Lake Como, it’s essential to plan accordingly, and that includes your outfit. I knew I needed to pick something that was pragmatic enough to wear throughout the day while still being picture-ready, as I wouldn’t forgo getting the shot! I landed on wearing an all-black outfit with pops of pistachio green; it’s a color pairing that exudes effortless elegance, IMHO. But I knew with the look, I’d need to be able to style some of the pieces I already packed—i.e., my Steve Madden Mesh Ballet Flats, Freja New York Shoulder Bag, Jenny Bird Chunky Duone Hoops, and my Prada sunglasses—in a new way. I paired them with a black linen halter top from Reformation, a black full skirt from Free People, and a light black cardigan from Sézane. (Although, I didn’t need it because it was the perfect sunny day.) I added a small green rosette pin along with an Italian-inspired printed phone case from OtterBox. Overall, the look was perfect for the day, as it was incredibly comfortable and secured me so many compliments as we explored Lake Como.

The first part of our day was all about exploring the lake by boat until lunchtime (in true Italian fashion). If you’ve ever found yourself following along as influencers spend their summers in Italy, then you’ve likely already seen the viral alfresco spot Giacomo al Lago. Located at the historic Grand Hotel Tremezzo, the restaurant boasts an incredible patio adorned with orange and white umbrellas that overlooks the glistening lake and vibrant mountain vistas—no words can adequately explain the beauty of this place, so I won’t try further. However, I will note that because it’s become such a hot spot, it can be nearly impossible to book a table in the peak of summer, so consider that while you’re planning. Nevertheless, if you do manage to nab a table, you won’t regret it, as the restaurant offers some of the freshest seafood in the area. Although, they do offer other dishes, too! My favorite one happened to be their take on the classic Italian dish cacio e pepe: stuffed tortelli with lobster on top, prepare tableside. Don’t tell me if you don’t order this dish, because I don’t want to hear it.

After filling up on seafood, we returned to our boats to head to a nearby small town called Bellagio. Although it’s a bit more touristy than other parts of Lake Como, its charming storefronts, cobbled streets, and incredible views make it worth dealing with the crowds. The shopping was noteworthy, as the island is filled with quite a few small vendors selling hats, bags, jewelry, and even pasta. But one of the best shops was Tessabit, a boutique with a curation of all the designer brands you’d want to wear on a trip to Italy—think Loewe, Pucci, and Jacquemus.

Even if you don’t end up splurging on an item here, window shopping alone will make you feel like you own your very own villa on Lake Como. And if that’s not enough to satisfy you, you can always book a tour of the Villa del Balbianello (where they’ve filmed multiple blockbuster films). Although you can meander about the property freely, if you want to go inside the villa itself, I’d recommend it booking a private tour. We learned quite a bit about the property. Plus, we got to pretend we lived in that part of the world for a tiny bit.

Day 4

WEARING: Jenny Bird Chunky Doune Hoops ($138); Prada Symbole Sunglasses ($517); Reformation Top; Aritzia Bubble Skirt; Steve Madden Dreaming Mesh Mary Janes ($90); Freja New York Caroline Bag ($258).

After spending most of the third day of the trip away at Lake Como, it was nice to return to Milan. The itinerary for the last day was about finishing some of the things we hadn’t gotten around to yet, whether that meant seeing specific sites or doing a little shopping. Since I knew that much of the day would be spent away from the hotel, choosing an outfit that allowed me to move effortlessly around the city while maintaining an air of elegance was imperative. I decided to pair my beloved white bubble skirt from Aritiza with the now sold-out off-the-shoulder rosette top from Reformation. I finished the look with the other accessories I had worn throughout the trip, including my favorite shoulder bag and shoes.

I wore my Freja New York Caroline bag more times than I could count on the trip, because its minimal shape, long strap, and spacious interior made it easy to carry while walking around Milan. But the best purchase for the trip had to be my Steve Madden Dreaming Mesh Mary Jane Flats—which definitely saved my feet on this trip. On the last day, I spent more than twelve hours out and about, but never once did my feet hurt. They made enjoying everything I did on the last day a walk in the park or, in this case, through cobbled Milanese streets.

Once my outfit was sorted, I could focus on my plans for the first part of the day, which included a guided walking tour of old-school “botteghe” pastry shops. Usually, I wouldn’t say I like walking tours, but the OtterBox team researched to find a former New Yorker and food writer, Elizabeth Thacker Jones, who was willing to show us around the city. Witnessing Milan from the perspective of an expat turned local allowed us to hit up all the off-the-radar spots. We began the tour at Pasticceria Marchesi, which was founded by no other than Mother Miuccia Bianchi Prada herself. The café nestles hidden above the crowds of tourists at The Galleria Vittorio Emanuele II, its spacious pistachio-green interior offering guests the chance to sit at a table or stand like a local (we do the latter, for the record).

After getting our fill of pastries and caffeine, we set out to see the rest of the city by walking through various neighborhoods to learn the history of the town—including the Quadrilatero D’Oro and Brera district—until we decide to grab gelato before our next tour. We ended our tour in the most unassuming market, Peck; it’s the place you imagine Italian nonnas going to to get their groceries. You wouldn’t expect to have incredible gelato, yet every girl in our group was giddy with joy because it was that good. Ultimately, exploring Milan through creamy delights is the best way to cosplay as a local.

Decidedly full for the time being, we went to visit Duomo’s terraces. I should preface this by saying that in the few times, I’ve visited Milan, I’ve always gone out of my way to avoid doing things that are too touristy, but because our group was so fun, I decided to go (no regrets, either). If you’re anything like me, it’s worth making an exception to the rule of avoiding “tourist traps” to see the top of the Duomo because it’s incredible. The key to enjoying this excursion lies in the planning, as you’ll want to book your tickets to the top beforehand to pick an optimal time (editor’s note: they’re different tickets from the ones to get inside the Church).

Secondly, you’ll want to wear a comfortable outfit; specifically, pay attention to what shoes you wear because there are a lot of steps. While there’s an elevator, mobility can be a challenge while you’re up there, so that’s worth considering. Also, it’s a rooftop, so please bring sunglasses and layer on the sunscreen if you plan on staying up there for a while. Lastly, my final suggestion for making the most of this activity is to lean into the tourist vibes by taking lots of pictures. Get creative with the angles! The worst thing that could happen is that you accidentally drop your phone, but if you’ve got an OtterBox case that’s been drop-tested, you’ll be fine.

Following our time at the Duomo, we decided that we had to do some last-minute shopping. Because when in Milano, amirite? Coming out of the historic church, we started our journey by walking directly across the plaza to the city’s largest mall, the Galleria Vittorio Emanuele II. While most might come to this spot for the incredible architecture, it’s worth doing some window-shopping as it has some of the world’s best luxury brands there—ahem, Bottega Veneta, Fendi, Gucci, and Prada. After a fair amount of browsing, we returned to the shopping area our tour guide showed us earlier (Quadrilatero D’Oro) to hit up a few stores. With the former, it can be hard to know which second-hand shops are worth visiting in Milan, but there was one place we stopped out as we were meandering about the city that’s worth adding to your radar: Cavalli e Nastri. The shop had a cute space with an excellent curation of vintage bags, jewelry, and apparel, all in good condition.

After scouring through the vintage store, we decided to hit up a few other stores, most notably the consignment store, DMAG. I learned about this hidden gem from my lovely colleague, Eliza Huber, who suggested I visit it immediately upon arrival. When I began sharing the news about this store, everyone in the group was begging to go; it turned into a whole thing. We spent hours pillaging through designer bags, shoes, and clothes at both locations in the city—I can only describe the scene as a group of girls being feral. We were so engrossed in the shopping experience that we realized we were almost late to our dinner plans for the night. Be warned, if you go here, you may have a hard time leaving.

Despite running late from our shopping exercise, since it was our last supper, I had to slip into one last ensemble before we left the hotel. Knowing we would do a cooking class with Foodspot, I wanted my outfit to serve. I landed on styling a two-tone strapless dress from Aritiza with an oversized bubble necklace and black ballet flats; it was a spicy combo but still sweet. It was the perfect ensemble for the evening as it was comfortable enough to wear while navigating the kitchen but still chic enough to enjoy the space’s sophisticated dinner table setup.

As someone who’s taken cooking classes before, I found this one the most fun I’ve ever taken. We learned from a local chef, Tommaso Fara, who walked us through how to make various traditional Milanese dishes, including pizza, risotto, and tiramisu. Unlike some classes where the instructor might be talking at you, it was completely interactive, allowing each of us to contribute to the cooking process—let’s just say the girls keep setting up their OtterBox tripods to record the entire time! The experience was the perfect way to end the trip, as it embodied what Milanese culture is all about: eating great food in great surroundings with great people.

Departure

WEARING: Jenny Bird Chunky Doune Hoops ($138); Prada Symbole Sunglasses ($517); ASOS Satin Coat; Ninety Percent Dress; Steve Madden Dreaming Mesh Rhinestone Mary Janes ($90); Freja New York Caroline Bag ($258).

By the end of the trip, I was not ready to leave Milan. I had to will myself to get on the plane by wearing a chic outfit to rally my spirits. For the flight, I wore a gray dress from Ninety Percent, a long black satin coat from ASOS, and my Steve Madden ballet flats. I always like to be a little dressed up at the airport, but I also wanted to bring back some of that stylish Milanese energy home. The outfit helped a little, but returning was still quite hard. It’s hard to come back from vacation, even more so when you’ve just been on one of the best trips of your life (this was that for me). A part of what made this Milan trip so great was because of the incredibly well-planned four-day itinerary by OtterBox—which I’d recommend anyone visiting Milan recreate on their own terms. But mostly, it had to do with the fact that at every point of the trip, I was able to learn something new. Whether it was finding out where to shop, the history of the city, or the sustainable textile industry, Milan taught me so much. I’ve learned that while we may not be able to stay on vacation forever, the memories we take home with us are as durable as an OtterBox case.