What To Wear In Milan In October: Real Outfits I Wore

So, you’re going to Milan in the Fall! That’s wonderful.

Hello and welcome—I’m glad you’re here. You could have stopped at Googling “Italy October Outfits,” but you took the extra step, looking for what to wear in Milan in October, and you’ll be thanking yourself for it later.

Milan’s weather in October can be a little temperamental, to say the least. The outfits you’d wear in Bolzano or Florence during the same week might completely differ from those in Milan. And it’s not just the style that changes, but also the number and types of layers.

But don’t worry—I’m here to explain it all and give you plenty of outfit inspiration.

Let’s begin!

How Is Milan In October

By now, you might be scratching your head, wondering what Milan is like in October.

My earlier comment about the temperamental weather wasn’t meant to scare you or put you off from visiting—far from it. I just want to make sure you’re well-prepared. I get it—I’m usually pretty good at figuring out the weather and what to pack, but Milan was a different story.

Even though I checked the weather forecast and watched the webcams daily during the two-week countdown to my departure, I still couldn’t decide what to pack.

Here’s why: one minute, it was raining, and the next, it was sunny. Temperatures weren’t too bad, but from the webcam, people looked like they were dressed for winter.

It was the opposite of what I remember packing for Italy in October 2023, when I visited the Dolomites and Florence. You can see what I wore last year here.

Milan October Weather

Just three weeks before we arrived, Milan and other areas in the Lombardy region experienced serious flooding due to heavy rains and overflowing rivers.

Luckily, that only lasted a couple of days. Yet, the rain continued in the following weeks, so I prepared myself to see Milan mostly in the rain.

This turned out to be one of my rainiest holidays—right up there with London in December and Budapest in April.

It rained at least six days out of the nine we spent in Milan, but it wasn’t all bad. It was raining when we arrived and for most of the next day, but with an umbrella, we managed just fine.

We had a nice weekend – free of rain but mostly cloudy. Then the rain came back strong on Monday, and we had to spend most of the day in our Airbnb—it was pouring!

We finally made it out at 3 p.m. and had a lovely evening near the Duomo. It was still drizzling, but nothing we couldn’t handle with an umbrella.

Tuesday brought light rain, while Wednesday was mostly sunny.

On Thursday, it rained heavily until 10 a.m., but then it turned into the sunniest and warmest day of our trip. Unfortunately, we had to cancel our day trip to Verona because of a weather alert—the rain there was even heavier than in Milan.

We lucked out on our final day, which was another sunny and warm one.

This should give you a clear picture of what to expect when visiting Milan and the Lombardy region in October.

Of course, no October is the same. Last year, the weather was about a month behind, and it still felt like summer in October. This year, the weather seems more in sync with the seasons.

Nonetheless, if you’re visiting Milan in October, expect it to be quite chilly for October in Italy, as well as cloudy and rainy. But don’t worry—you’ll likely enjoy a few sunny days, too!

What Are People Wearing In Milan In Fall

Before I share what I wore in Milan in October, I want to let you know about a separate article I’ve written on Milan Fashion for Fall and Winter. In it, I share all the looks that inspired me and the styles I managed to capture during my stay. I wished I had a camera in my eye that could snap a picture every time something caught my attention!

While that isn’t possible, I did my best to capture the essence of what the locals were wearing. Check it out here: Milan Winter Fashion: 2024/25 Street Style.

My Milan Outfits For October

Last year I shared my Italy October outfits and that post went viral on Pinterest. I am glad many found it helpful, so I thought this year I would share more location-specific outfits from my Milan Fall trip.

If you’d like an inside look at my process for choosing these outfits, you can read my Fall Italian Capsule Wardrobe post.

Many of these outfits were inspired during that process. I also had to factor in the rainy and cold weather, plus that time of the month.

I went with a black, brown, beige, denim, and gray palette. All the pieces fit well together, making it easy to swap if the weather required it. However, I wore my outfits exactly as I planned.

If you’d like to know my process for planning and packing my Italy outfits, you can find it all in my Italy Packing List & System.

Day 1 Outfit

If you’ve read my other Italian fashion posts, you know I emphasize that us Italians love wearing black, no matter the season.

Black is a safe choice during that time of the month and when it’s wet outside. But it also makes me feel elegant and put together.

For the first day I opted for an all-black outfit with a houndstooth blazer. Would you believe it if I told you that blazer is from Shein? It was a bargain and it looks much more expensive than it is.

This is what I wore to explore Brera, which as I had envisaged became my favorite neighborhood in Milan.

Outfit details:
Black cigarette trousers from Zara
Black Intimissimi thermal
Black Shein scarf
Houndstooth blazer from Shein
Black leather loafers from Aldo
Black Longchamp bag in medium

Day 2 Outfit

Looking back at the pictures, this was my favorite outfit, so much so that I packed that jacket specifically for this one outfit. While I love a monochrome look, I adore an all-black outfit.

I wore this for my shopping day in Milan. It was more of a window-shopping kind of day, as I was capturing content and making notes to share on the blog. But my husband bought a black overshirt from Zara, while I eyed a few pairs of loafers which I didn’t end up picking.

Outfit details:
Black jeans in style 501 from Levi’s
Black knit with buttoned sleeves from Zara
Black Shein scarf
Black Zara cropped jacket
Black Aldo leather loafers 
Black Longchamp bag

Day 3 Outfit

This is the only outfit I regret wearing because I felt so cold in the morning. I wore light tights but my legs were freezing. 

If you, like me, easily get cold, my advice is to opt for ticker tights or skip wearing a dress/skirt in Milan in October.

It was a Sunday and we spent the day in the Duomo area.

Outfit details:
Black A-line dress from Zara
Black Shein cardigan
Skin color tights from Calzedonia
Aldo loafers
Beige trench coat from Stradivarius
Black Longchamp bag

Day 4 Outfit

This was the rainiest day of our trip. It rained heavily all night up till 3 pm in the afternoon. After then, it kept drizzling until nighttime. 

We went out at 3 pm and spent the afternoon and evening enjoying the Duomo area at night. Walking with the umbrella and popping in and out of museums was very romantic, and felt like a true Fall evening in Milan.

Outfit details:
Massimo Dutti jeans
Levi’s white trainers
Zara gray sweater
Shein houndstooth blazer
Longchamp bag
Black Shein scarf

Day 5 Outfit

This was our first day trip from Milan. We went to Como city on Tuesday. It was still cloudy and drizzly, but it gave us a few moments without rain.

If you plan to visit Como, wear comfortable shoes, as this was one of the days we walked the most.

Outfit details:
Black Levi’s jeans 501
Black Tshirt from Mango
Black Shein cardigan
Stradivarius short trench 
Levi’s sneakers
Black Longchamp bag

Day 6 Outfit

Day 6 was another day trip, my favorite one. We went to Bergamo, and spent most of the day in Bergamo Alta. I really recommend a visit, or even spending a weekend there. There’s so much more we could have done.

My day 6 outfit was mostly Shein.

Outfit details:
Shein jeans by Dazy
White thermal Tshirt, also from Shein
Shein houndstooth blazer
La Redoute beige cardigan from Villa
Burberry style scarf
Black Longchamp bag
Levi’s white sneakers

Day 7 Outfit

This was another classic fail-proof outfit I plan on re-wearing, although I’d like to swap the jeans for a better one.

It was a Thursday and we were supposed to visit Verona. I had booked our train tickets, but we decided not to go because Verona had a flood alert. 

Instead, we did the Navigli itinerary I had planned for the next day.

Outfit details:
Shein Dazy jeans
Levi’s white sneakers
Oatmeal knit from Zara
Beige Villa cardigan from La Redoute
Stradivarius short trench
Black Longchamp
Burberry-style scarf

Day 8 Outfit

On our final day, we just repeated our favorite activities – breakfast in our favorite Milan cafe, mooching around the designer shops in Via Montenapoleone, followed by both Galleria and Rinascente.

I went with another smart casual look, and I loved it, especially paired with the loafers.

Outfit details:
Massimo Dutti jeans
Zara cropped striped blue shirt
Stradivarius trench coat
Aldo black loafers
Black Longchamp bag in medium

Milan In October Packing Essentials

If I could do it all again, this is what I’d pack:

1. A classic beige trench coat – long or short.
2. A light black coat – medium length.
3. A classic well-tailored blazer.
4. Two pairs of tailored black trousers. I packed trousers and black jeans, and it was a great choice.
5. Two pairs of jeans – darker and mid-wash.
6. Warm tank tops and longer sleeve light thermal vests.
7. Medium warm fitted sweaters. Baggier sweaters will not keep you as warm!
8. A pair of black boots – booties or mid-calf.
9. A pair of white sneakers.
10. A pair of leather loafers, or you could buy those there.
11. A canvas waterproof bag that’s roomy and goes with all your outfits.
12. Three scarves – one black, one beige, and one with a pop of color.
13. A nice set of earrings and necklace, with your favorite stack of rings.
14. Light long-sleeved pajamas. Even without heating on, the buildings are fairly warm inside.
15. A light rain jacket you can throw on, in case the rain gets really heavy.

In case you didn’t know, I have a full packing list you can use when packing for Italy in the Fall. I also have one for Winter, Spring, and Summer. You can see them here, and also get your free downloadable copy.

Milan In The Fall: Style Mood Board

Before you go, don’t forget to pin this:

If you want to dress like the locals, these are the colors to opt for:

1. Black jackets, coats, trousers and shoes.
2. Brown blazers and accessories.
3. Gray sweaters or coats.
4. Beige trench coats or coats.
5. A touch of burgundy – sweater, scarf, handbag, or tights. 
6. White and creams for layering.
7. Navy and jeans.
8. Dark greens, if they complement your skin tone.
9. Don’t be afraid to add a pop of color.
10. If you wear tights, opt for a patterned pair. They look great with cropped trousers too!

Want More Fashion Content?

If you enjoyed this post, please give it a heart and share it with a friend. It helps my little blog come across more lovely people like you.

And before you go, save these articles for another coffee break read:

The 10 Pillars of Italian Fashion Style

How To Build An Italian-Inspired Capsule Wardrobe

How To Dress Like An Italian Woman

You can browse all my Italian fashion articles here.

A presto,

Alessia.