From Prada to COS—Here's Everything I Packed and Wore for Milan Fashion Week

I'm usually a staunch supporter of traveling with only one carry-on suitcase. Checking luggage is a risk, especially for someone whose sartorial possessions are akin to children (don't come for me, please), so unless it's absolutely necessary, keeping my travel companions by my side at all times is essential to flying stress-free. Attending Milan Fashion Week, however, is the exception. Between shows, dinners, presentations, and parties, I already needed a lot of outfits. Add in the idea that I won't have my closet to fall back on if something I thought I wanted to wear didn't click the day of, and you can probably see why ample options were important. In the end, I picked out two pieces of luggage: Tumi's International Carry-On and Rolling Trunk, both in aluminum for maximum protection.

Luggage Details

But you didn't click into this story to read about my luggage (or maybe you did). You came for outfits, of which there were many. Ahead of my trip, I do what I always do before fashion week: add photos of every cool item I own into a Google folder that I then reference to create a plethora of worthy outfits. That way, while I pack and get dressed, I'm not panicking about what to wear. There are a million things to think about during fashion week—my own outfits shouldn't be one of them.

Below, see exactly what I wore during Milan Fashion Week to Gucci, Max Mara, and more.

Day One: Gucci

Milan Fashion Week started off with a bang at Gucci's F/W 25 show, the Italian brand's first since news broke that Sabato de Sarno would be stepping down as creative director. For my first Gucci show, I wore an easy blue button-down shirt tucked into a red velvet Blazé Milano midi skirt. The color combination felt very Gucci to me, especially with the velvet. Since it was raining and slightly chilly in Milan this day, I added a pair of tights to keep me warm, as well as a pair of chunky-heeled, round-toe pumps I recently got at Massimo Dutti. They're so comfortable and great for walking between shows. To finish off the look, I wore all black accessories, including Khaite x Oliver Peoples wire-rim sunglasses and my 1995 Re-Edition Prada bag.

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Day One: Dinner at Ristorante Berton

I flew to Milan with the luxury watch brand IWC for an event it held in the Italian fashion capital ahead of fashion week, so in the evening, we had a welcome dinner at the fine-dining restaurant Ristorante Berton. The food was incredible, as was the company. For the dinner, I wore an Altuzarra dress from the brand's F/W 24 collection that I've loved ever since it debuted on the runway. The fabric is really thick and luxurious, making it fit in all the right places. I also wore it during New York Fashion Week and didn't care at all that I was repeating outfits—it's that good. With it, I added a burgundy patent-leather Bulgari bag and black patent-leather Ferragamo boots.

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Day Two: Antonio Marras, Diesel, and Brunello Cucinelli

Day two's calendar included a mix of shows, presentations, and cocktail events. Oh, and shopping—we stopped by an old Céline pop-up at the boutique at Modes. For the day, which started at 10 a.m. and ended around 1 a.m., I kept my look pretty simple and easy, opting for a navy blue sweater, vintage Tom Ford for Gucci leather pencil skirt, and the only coat I brought on the trip, a chocolate-brown car coat that I scored at a recent Fforme sample sale. I've been loving pairing pencil skirts with tall boots, especially slim-fitting ones like these vintage Jimmy Choo suede stiletto boots. Finally, I tied in my navy sweater with my navy nubuck-leather Alaïa Le Teckel shoulder bag that surprisingly fits so much.

Day Three: Max Mara, Blumarine, Emporio Armani

When in Milan, one must wear Prada, and that's not just me being dramatic. It's practically the law. For day three then, I really had no choice but to bring out the baby-pink satin miniskirt from the S/S 22 collection that I scored at a truly unbelievable price at an outlet mall outside of Barcelona last summer. Since it wasn't actually miniskirt weather yet in Milan, I paired the skirt with a black Proenza Schouler sporty jacket, taking cues from Prada's S/S 25 collection, where formal skirts and dresses were "wrongly" styled alongside technical outerwear. Lastly, I threw on a gray cashmere J.Crew sweater, black Prada handbag, and slingback Prada wedges that are shockingly easy to walk in.

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Day Four: Sportmax, Moschino, Missoni

Whenever I can wear a piece by the brand showing, I'm going to, which is how I ended up in this cream, split-hem midi skirt by Sportmax that I recently ordered from Cettire after months of searching for the slightly different black-and-white version. (I'm still on the hunt for that one if you've seen it—my DMs are very much open.) I repurposed the navy blue cashmere polo I wore in an earlier outfit, tucking it into the skirt and adding a pair of brown Calzedonia tights, my Alaïa bag, and Massimo Dutti pumps. It's crazy what changing a skirt can do to make an outfit feel completely new and different.

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Day Five: Ferrari, Prada Re-See

By day five, I hadn't worn two of my favorite wardrobe items that were packed, so I knew they had to make their debut. Plus, I was going backstage at the Ferrari show, and as a die-hard member of the Tifosi, it was important that I support the team's colors (minus scarlet red). As a result, I chose to pair a black Carven sculpted tunic that I bought at the brand's store in Paris during the Olympics with a bright-yellow satin Prada skirt from the same outlet-shopping trip (and collection) as the above pink skirt. I accessorized with the same black Prada accessories as I mentioned earlier, as well as my Cartier Tank Must that I wore every day throughout Milan Fashion Week.