What to Wear in Milan, Italy This Fall

Last week I took a short trip to Milan, Italy with my school’s fashion program! We spent our three days exploring different art galleries, seeing popular tourist attractions, and shopping around the city.

As you probably know, Milan is the fashion capital of the world so I wanted to come dressed and ready! I was a little torn on what to pack as temperatures were going to be in the mid-seventies despite it being the middle of October. To my surprise, I nailed it and am sharing all three outfits with you today. Enjoy!

Color Blocked Moment

After two weeks of living in Italy I quickly learned that trousers are a European’s best friend. It’s rare you catch them in jeans but a pair of trousers… almost always. I got this pair from Princess Polly early in the semester and have been wearing them nonstop. I’ve never had a pair of pants fit me so beautifully along the waist. I wear a 2 and am a 24-inch waist. They come in dozens of colors but cholcate brown is my jam come fall time.

Up top, I wanted to lean into the silk scarf trend. I’m tying mine in half for a cute strapless look. It was a bit brisk in the morning so I popped on a bollero. These are another item that I never wore until I moved to Italy, however they are so common and truly so practical. I’m not usually a fan of mixing brown and black but this scarf made it so easy to do so. I love the way these two hues play off of one another here.

Typically, I’d opt for a pair of chunky heeeled boots with this, and it’d certainly be more of the ~Milano~ vibe, but I knew I’d be on my feet all day so platform sneakers it is!

top // pants // bollero // sneakers // headband // purse 

Tres Chic

You know what they say, you can truly never go wrong with a little black dress. This one is anything but boring with the huge balloon sleeves. This dress was giving “walk of shame” energy so I popped on a Tory Burch belt to cinch the waist and give it some shape. As you can see, it did just the trick!

It was warm enough to forgo tights so I’m rocking the bare legs and throwing on a pair of black leather boots. This city is all about heels so when in doubt, reach for something with a little height. These Steve Madden boots have a higher shaft that elongates and slims the legs in no time. Big fan!

To accessorize I’m layering on gold necklaces, grabbing my favorite leather crossbody, and adding a fun baker-boy cap. Tres chic!

dress // boots // belt // purse  // hat 

Feeling Fall

It’s finally starting to feel a bit like fall. Still warm enough for bare legs but chilly enough for layers. I’m putting my own spin on this transition season starting with a white oversized sweater up top. I’m then front-tucking this into the cutest gingham skort. These are my favorite pieces when on the move—business in the front, party in the back. You truly can’t go wrong!

I’m then popping on my all-time favorite boots regardless of the occasion—the Steve Madden Hutch. These are among the most comfortable shoes in my closet. They have just the right heel height and look good with literally everything… leggings, jeans, skirts, you name it. SO versatile! Of course, I’m adding matching socks to peek out that top and grabbing the new purse that I had handmade in Africa to match!

sweater // skort // socks // boots // headband // purse (handmade in Africa)

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That’s a wrap for this short and sweet outfit guide. I was so happy to be in outfits that could easily transition from daytime sightseeing to evening drinks. I loved Milan and certainly left with some fashion inspiration up my sleeve. I hope this blog post gave you a few outfit ideas. Catch you later this week with some Switzerland looks!

With love, McKenz

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Related Post: Venice, Italy Travel Guide Fall 2022
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