Whether you’re planning a trip to Milan this fall or winter, or want a peek into how Italy’s most stylish city dresses for the season, I’m glad you’re here! While exploring the streets, I captured 17 beautiful looks, and I’m excited to share them with you as we dive into the world of Milan street style.
PS: Even though it’s mostly me chatting here, you can now find me on TikTok @… – say hello, and let’s talk all things Italian fashion over there!
If you’re curious about my style, I’ve also shared my Milan outfits in a separate post. As a petite lover of minimalist, monochrome, and classic looks, I blend Italian fashion elements with pieces I love. That’s what I plan to showcase on TikTok, alongside Italian food, and snippets from Italy.
Now, let’s see what the Milanese are wearing this fall. Shall we?
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Milan Street Style: 17 Looks To Recreate
Milan is a cold city, which means that once October begins you will see people in their outerwear. So while you are not going to see the whole outfit, I suggest you focus on these details:
- The type of outerwear they are wearing.
- The trousers or tights peeking underneath.
- The shoes they are pairing those with.
- The color combinations.
- The bag they are wearing.
That’s going to be helpful whether you need help packing for Milan, another cold European city, or want some inspiration for the cold rainy outfits you will be wearing this season.
Rain Coat Looks from Milan Streets
The Milanese are accustomed to rain, especially this time of the year. Look at how many raincoats looks I captured.
Although the length and color might differ, they have one thing in common – they are not trench coats.
The locals seem to prefer Mac coats. I think that’s because it’s stylish but in a more effortless way, which ties back to the sprezzatura concept.
Another practical reason I can think of is that it’s easier to wear over blazers, both for work and the weekend. And we all know Italians, me included, love to wear them, but you can’t fit those under a fitted trench coat!
Look at the outfits below and consider this information:
- All three women look local.
- These pictures were taken on three different days: Sunday, Tuesday, and Thursday.
- The first woman seems to be shopping.
- The second is likely out of work.
- The third might be out for a passeggiata with a friend – the woman in front of her, or going to a meeting, who knows.
All three jackets seem light and baggy enough to leave room for a blazer, and I am pretty sure the lady in look number two is wearing one.
What do you think?
That overall look is classic, from the color combination to the choice of shoes and bag.
PS: Speaking of color combos, navy and black is a color combo I saw a lot in Milan, among both women and men.
This last look is more of a waxed rain jacket but it has a similar style to the ones above.
Belted Coats Looks In Milan
Even though trench coats might not be as popular in Milan, among the locals, I saw many tourists wearing them, including myself.
The look I captured below, I am not sure whether it’s a tourist or a local (if I had to guess, I’d say she’s French), follows that navy street style element I shared earlier.
I also noticed that the younger generation in Milan prefers baggier looks, which is in line with the cool trend that has been going on for a while.
That shows even through the way they choose to wear their outerwear. Look at the young lady below. Rather than cinching it in, she’s purposely decided to leave it open with the belt hanging at the back. Of course, she has the height for it. If someone like me were to do that, you would only see my face peeking out of the coat.
Do People Wear Jeans in Milan?
Of course, they do!
I think there’s a big misunderstanding about Italy and jeans.
It’s not that Italians don’t wear jeans, but they wear them differently. I think there’s room for a discussion about this in a separate post.
For now, you should notice that all the looks I captured featured some sort of tailored jeans. See below.
By tailored I mean this. They are either cropped to show some leg, or they are long enough to cover the shoe.
They also wear them with a structured piece, like a blazer, or a stylish mac coat.
Look at this look for instance. The woman above is wearing a fitted but straight-leg pair of jeans, which I managed to spot only by zooming really in. She paired it with a navy blazer, and opted to belt it following the trend I am seeing throughout the shops. The color match is impeccable, thanks to the very dark jeans wash.
Those who wear jeans without a blazer or a longer coat, like the lady below, tend to have a very unique and cool style.
Milan Street Style Looks Featuring Skirts
As expected, I didn’t see many locals wearing skirts, and when I did it was almost always a midi length. Long skirts are certainly more stylish, especially if you have the legs for them. It’s also more practical and warm for the cold rainy season.
Another thing I noticed is that whenever the outfit featured tights, it was nearly always a very intricate and interesting pair. See the look below.
PS: If you want to buy your tights in Italy, I suggest Calzedonia. That’s where I buy all my socks too.
Most of those women wearing skirts without tights paired them with loafers. See the look below.
All Black Outfits In Milan
I am surprised I didn’t spot any more all-black outfits since I love them so much. However, the ones I captured are gorgeous.
The lady below is wearing a pleated black skirt, showing a little leg over her black boots. She finished the look with a belted black coat, which she wore open. I like how she chose to break the all-black look with another classic color, a white bag.
Look number two shows a mature lady wearing cropped tailored trousers under a wool coat. She finished the look elegantly with black pointed flats, black sunglasses and a black Louis Vuitton bag.
Milan Street Style Featuring Colored Looks
I must say I didn’t see many locals wearing a pop of color, unlike last April in Rome. It must be the season or the cooler vibes, but I didn’t mind it at all, since I fit right in.
I do however have three colored looks to share with you. The first two have a common aspect.
Can you see they are both monochrome?
That’s exactly how I would do a pop of color, to keep it elegant and classic.
I must say that green is not my favorite color, especially these shades, but both women styled it wonderfully.
The first is a true monochrome look, accentuated by the black over-the-shoulder sweater that finishes it beautifully.
The second look is more of a complementary color combination, as the jacket has both khaki and gold hues. It’s not a style I would go for, colored denim and a vintage-looking jacket, but it works.
Also, I am not sure if that’s suede. If it is, she is right on trend.
The third-colored look from Milan streets is my favorite. I am not sure I will feel comfortable wearing it, because I don’t like wearing bright-colored pants, but I am tempted, maybe I will give it a go next Spring. What I like about it is that only one element is colored, and all the rest is very classic and muted.
If I can see well, those pink trousers are corduroy.
More Milan Street Fashion
I hope you enjoyed this little chit-chat about Milan street fashion in October. I had fun capturing the looks and sharing them with you.
You can find a similar style section in this article: What To Wear In Italy in October, where I featured both Northern Italy and Florence street style.
Don’t forget to check out my Milan Outfits here.
And if you’d like to see the Milan street-style videos I captured, you can find them on my TikTok @.. Come say ciao.
For those trying to create more Italian looks or being fascinated about how Italian women dress, I suggest these two articles:
20 Must-Have Italian Wardrobe Pieces To Dress Like An Italian Woman
How To Dress Like An Italian Woman (coming next week)
Before you go, please give this post a heart and share it with a friend. Your support means a lot!
Stay elegant.
Ciao,
Alessia.
