What do you wear on a rainy day in fall?
I went looking for the answer in one of the rainiest cities in Italy – you guessed it, Milan.
I’ve curated a collection of rainy day outfits Milanese women wear in the cosy season, to inspire you to stay warm, waterproof, but without giving up that chic factor you likely love if you’re here.
Let’s see them.
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My Observations on Milanese Style in the Rain
Before I start showing you the outfits, I’d like to share a summary of my findings.
The first thing that surprised me is how Italian women are not afraid of wearing high heels in the rain, not even stilettos, and that’s also true for older women.
I think the first thing you want from your outfit in this type of weather is to be comfortable and safe. But I do get where the Italian women are coming from — they’re used to wearing high heels all day, and many of them feel comfortable enough to walk in the rain.
On top of that, it’s also very likely they’re only walking a short path from the car to wherever they need to go, and pavements in Milan are pretty smooth. You definitely wouldn’t want to walk in high heels on Brera’s cobbled stones!
Having said that, don’t worry, I’ve only chosen to show you the outfits that feature more appropriate shoes, because I know most of you won’t be wearing heels in the rain.
Another observation relates to more delicate fabrics like suede. I grew up hearing my parents say you can’t wear suede in the rain, or it will get ruined. Nowadays, suede and leather protectors are very common, so that explains why so many Milanese ladies looked unbothered with their wet suede boots and bags.
As for the type of garments most worn, as I envisaged, there were many trench coats, and long jackets and coats, way more leather than I expected, and of course boots of all types.
I also spotted a few outfits with sneakers, especially on Italians coming out of the train station or with a more casual look.
But the one thing I’d like to highlight is that Milanese sure have a corner of their wardrobe dedicated to rainy days. In fact, I kept seeing the most gorgeous raincoats; some had a trench coat silhouette, others were waterproof mac coats in unique colors.
Finally, as expected, most outfits I saw were as usual — chic, put together, and well thought out. So, we can conclude that no matter the weather conditions, Milanese and Italians still care about their appearance, even more than comfort.
Let’s get into the looks.
Trench Coat Outfits
We’re starting with trench coats. I have three examples to share.
First outfit: Cigarette pants with a nice crop so we can see the beautiful leather boots underneath, a cosy oversized sweater, and the classic trench coat. We can also spot a tonal scarf and a matching brown leather tote. The woman has definitely chosen a more classic casual outfit, but still very chic.
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Second outfit: This feels both very put together and very creative. It’s classic on top and casual on the bottom with those folded jeans hems and the very stylish sneakers. It’s definitely an Italian woman wearing it, and we get that from the matching bag and shoe. Underneath, she’s layering a classic white shirt and light blue scarf with a bit of tan to tie in those accessories.
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Third outfit: This is the one of the three I would want to wear. It’s the most minimal, chicest, and high contrast, which works well with my color season.
Don’t know your color season?
Find out here: Simplified Color Analysis Guide + Steps To Do Yours
I also love the cinched waist. We can’t see the outfit underneath, so I’ll tell you what I would wear: it’s clear she’s got something tucked into her boots, which makes me think it’s probably a pair of tights (Italian women don’t often tuck their trousers or jeans into their boots), paired with a black midi dress, or a skirt and a cashmere knit.
Mac Coats
Let’s move to the mac coats. I only have two to show you, but the first packs a punch.
Outfit 1: This is definitely my favorite rainy day outfit, not because I would wear it myself. I certainly don’t suit that green shade, and that long skirt would swamp me. But I love how the woman is having fun playing with different layers, making it look chic but cosy, stylish but comfortable, and also rainproof. And she even added a pop of color!
Shop Similar Rain Jacket
Outfit 2: I spotted this on a middle-aged woman out and about with her husband. They were both dressed casual but very tastefully. I was truly tempted to show you her partner’s look, but I’m going to reserve that for my men’s guides. Here’s hers.
It’s a tonal beige look featuring a pair of wide straight-leg jeans, designer sneakers, and a brown bucket bag. We can’t see her top. It’s perfect for a quick errand in the rain, or to grab a coffee, but even as a travel outfit. Perhaps she’s an Italian woman visiting Milan.
Leather Jackets In The Rain
The next set of outfits is all about leather jackets. I’m sharing three.
Outfit 1: We’re starting with another outfit perfect for women over 50, though I don’t see why a younger woman wouldn’t want to wear it too. It’s classy, with a good mix of vintage and edgy. Don’t you think so?
That suede skirt is gorgeous, and so is that vintage leather jacket. The bag and the booties finish the outfit impeccably, which doesn’t surprise me. Over the years, I’ve spotted plenty of chic older Milanese women.
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Outfit 2: It’s another skirt outfit, and it reminds me of something I noticed but forgot to mention in the summary above: Milanese women seem to prefer wearing skirts with boots over pants. That’s because it’s easier to get the bottom of your pants wet when you’re walking in the rain, or being splashed by cars. The skirt here is again a suede one.
Another note: Milanese love their black hunter-style boots, and we can clearly see they work perfectly with dressier outfits too.
Outfit 3: This final leather jacket outfit shows that you can wear jeans and sneakers, and even a roll neck and a beanie, and still look stylish. The leather coat is the piece that elevates the outfit, for two reasons: the longer coat style immediately dresses things up, hiding most of the casual pieces underneath, and the cinched-in waist makes the look feel more curated and intentional. This is cosy chic rainy day dressing, definitely not frumpy.
Shop Long Leather Coat
Coats for Cold, Wet Days
Next, I’m showing you five rainy day outfits that feature a coat. Not everyone feels the need to wear a waterproof jacket, especially if they’re under an umbrella. The one non-negotiable is the boots. Only one out of five women chose a different type of shoe, and you wouldn’t guess who.
Outfit 1: Here’s another outfit that’s very me — all black, low-heeled boots, and a coat that looks like a trench with a cosy velvet fabric. We can’t see what she’s wearing underneath, but the options are endless, probably a dress or a skirt with tights.
I want to mention how this is exactly how you should style yourself in the colder months and on a rainy day: you want your most interesting garment on top, even if it’s just the fabric, because that’s the one thing that’s going to be most visible. It’s what makes the outfit!
Outfit 2: This is my third favorite. The colors are perfect for my winter season; the look is chic and comfortable, warm and rain-appropriate. I love the matching plum boots, and I have the exact same blazer, which she’s chosen to layer under the coat. I mentioned earlier how much Milanese women (and men) love doing that.
Outfit 3: If you’re looking for the perfect outfit for a bad hair day in the rain, or one to help you protect your fresh blow-dry, save this. It also makes an ideal winter travel outfit. The hat looks edgy, but it’s also giving extra warmth and rain protection.
Outfit 4: This is the one coat look that skips the boots, worn by a woman over 50. She loves her heels and is confident enough to wear them on a rainy day, and I love that. It’s also one of the most stunning rainy day outfits I’ve seen. The grey and that almost light blue go perfectly together. The umbrella is the piece stealing the show. I want that umbrella. From my research, it’s from a luxury Italian umbrella brand called Pasotti, based in Mantua, another beautiful city in the Lombardy region.
Outfit 5: If you like a fur coat moment — Italian women certainly do — there’s no need to put it away on a rainy day. I love how this young woman is wearing hers with a light shirt dress and boots. It’s the perfect mix of contemporary and classic.
Rainy Day Blazer Outfits
Finally, if it’s still early fall when rain hits your city and you’re not quite ready for trench coats and leather jackets, you can always wear a blazer. As long as you have a good pair of boots and an umbrella, you’re good to go.
Have a look at how Milanese are doing it.
Outfit 1: What do you see? I see an outfit that’s smart-casual chic and could be complete as is. Those sneakers and socks give it a very cool “Milan girl goes to work” vibe, but I have a feeling there’s a pair of heels in that white shopping bag.
Either way, this gives you an idea of how to commute to work comfortably in the rain — and if you love the white sneakers-and-socks look, you can leave the heels at home. The blue and red pairing is interesting too, giving a nod to spring/summer while still feeling fall/winter, which makes it ideal for an early fall outfit.
Outfit 2: The last look I have for you is, of course, another all-black one. Is there anything more Italian and rain-safe than wearing all black? I don’t think so.
This could be a regular outfit the woman wears to work, but it could also be a shop sales assistant uniform — many Italian shops have all-black uniforms.
More Fall Outfit Ideas From Milan
So, did you find an outfit or two to recreate next time you wake up on a drizzling or pouring day?
Make sure to share this guide with your girlfriends. It will help them too, and it’s the best way to support my work. Thank you for that.
If you’re ready for all the beautiful layering that this season has to offer, I have plenty of Italian-style guides to inspire you. Pick your next read from this list.
How To Layer Like An Italian This Fall
Fall Office Outfits That Aren’t Basic
How To Style A Leather Jacket Like An Italian Woman
Fall Dresses Worth Adding To Your Closet
Before you go, I’d like to invite you to join Buona Settimana – my Italian newsletter. There are plenty of cosy season emails coming your way, and it’s the best way to chat directly with me about Italian fashion, food, travel, and life. You can write to me and I will reply to every single email, that’s a promise. I hope to see you there.
A presto,
Alessia
