End of Summer outfits in Milan doesn’t mean the heat has ended — it just means the wardrobe starts hinting at what’s next.
Nobody’s reaching for wool in 28-degree heat, but you’ll notice the palette shifting darker, linen swapped for slightly heavier cotton, a pair of sandals traded for loafers worn sockless. It’s subtle, it’s still weather-appropriate, and it’s surprisingly easy to copy.
If you’re looking to get more wear out of your Summer wardrobe, or you want a head start on bringing in Fall, here are 10 ways Milan is striking that balance right now, with real looks spotted on the street for each.
PS: If this is your first time on my blog, hello and welcome. I’m Alessia, the writer and founder behind Italy with an Italian. I hope you enjoy this post, and feel free to come join my Italian newsletter – Buona Settimana. It’s like chatting with an Italian friend!
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1. Wearing Long Sleeves Rolled Up, in Light Fabrics
The Milanese women that work in an office, especially in top positions or strict corporate settings, wear these throughout Summer. But for all the others, bringing this back feels very good. It means the weather is starting to feel breezy enough to endure the longer sleeves, and if you love Italian style you know that this wardrobe piece is essential for creating the most beautiful timeless outfits – from tucking it into midi A line skirts, to styling it with pants, and why not even jeans, to wearing it loose over a tank top for a modern minimalist look.
Here are two looks I spotted, one is very bright and white, and the other one is darker and moody. Which one would you wear?
Layering a Light Over The Shoulder Sweater
Let’s face it. Most of us wear it because of the styling, not so much the warmth. However, if you pay attention you’ll realize that that little piece covering your shoulder and back does something to the temperature of your outfit. So in reality it’s also a practical way to dress for the transitioning season, especially since you’re basically found a stylish way to take your jumper with you without having to carry it!
This is an unmistakably Italian look, one that might feel a little overdone since everyone is doing it. That’s why I want to show you three different looks I spotted in Milan, and honestly it wasn’t that easy, because most of them were actually tourists. These three looks aren’t.
The first it’s probably the best one to copy if you’re traveling to Italy or Europe this end of Summer/early Fall. It allows you to pack your Summer dresses and elevated flip flops. Thong sandals were really in this Summer. And by packing a few light jumpers, you’ll quickly take your outfit from hot Summer to breezy September and October days.
Look 2 is for cooler modern women, who love playing on the timeless Italian style vibe by swapping the fabrics and the proportions for an edgy look. If you don’t want to do a skirt, I can easily envision this worn with the same colored denim but in the form of a wide leg pair of jeans.
Finally, is this very chic look that belongs on a very sophisticated Milanese woman in her 30s, 40s, or even older than that (if you’re surprised read this: Ageless Style). She could be going to her creative workplace, or running errands (yes many Milanese women look like this to run errands, and we should get inspired and do the same, because that’s likely the life we’re dreaming about, is it?). This looks like a set with a modern take on the midi skirt, which comes with a matching jumper or shirt.
Side note: if you’re fascinated by the way she is dressing up a plain, slightly oversized, grey tee, I am there with you. Read this next: How to Style a White Tshirt The Italian Way
Starting to Wear Loafers Again
If there’s one thing the Milanese never put away in Summer it’s these, because while they are far apart and rare, this is the perfect option for Summer rainy days. It’s also great if you prefer a stylish closed footwear option when traveling and sightseeing, especially if you’re going further North in Europe where the weather is cool and breezy.
Other than that, loafers are the perfect transition shoe, maybe it’s because you can wear them without socks (in reality, most Italians, including me, wear them with invisible ones!) unless they are espadrilles style and they haven’t got sensitive feet like mine.
The sock part is an important detail, because the last thing you want to do when it’s still hot is go out wearing clearly visible socks, that might be ok for Winter (especially if you match or contrast your sock) but a little weird for September, unless it’s an element of your cool styling.
Think about all the ways you can wear loafers this time of the year – with your dresses, both Summer and transitioning ones (think of a short sleeve shift dress, or a long sleeve shirt style), with jeans and a Summer top, with a suit layered with a sleeveless camisole.
Read this for more ideas: How To Style Loafers Like An Italian Woman: 35 Outfit Ideas
Wearing Light Blazers
Is there anything more chic than a blazer worn over the shoulders? Probably not, but that’s not very practical when your blazer needs to warm you up. This is why right now is the time to do this. You’re using your blazer for extra warmth but most importantly for extra styling.
Let’s see three different ways Milanese women are doing it.
The first is layering it over a very Summery silk dress. I love the monotone look, and I also appreciate that the color palette is completely opposite to the season we’re moving into, yet the blazer and shoes make it feel appropriate.
The second is a perfect office end of Summer outfit. You’re wearing light colors, and then topping the outfit with that very classic pumpkin color blazer and a matching neck scarf. Very chic but also practical.
Outfit 3 is the more modern of the three, perfect for younger women who have a timeless style, but one that works at any age, with the right fit and accessories. Would you wear this to travel or to grab a coffee with a friend?
Wearing More Pants
This one is really easy. If you’re the type of woman who only wears dresses, skirts, and shorts come Summer, swapping back to pants will immediately make your outfit feel end of Summer, even if everything else you’re wearing stays exactly the same.
Here’s a perfect example: rust-colored suede wide leg trousers, paired with a navy floral short sleeve shirt tucked in, a thin white belt, and white mules to keep the look feeling like Summer hasn’t fully left yet. The suede is really doing the work here — it’s the one detail nudging the outfit into Fall territory, even though the print, the bare ankles, and the cropped sleeve all still red as warm weather. One fabric swap, and the whole thing shifts.
Read this for inspiration: Wide Leg Pants Outfits: Italian Looks For Every Season
Adding That Neck Scarf
No matter how chic it looks wearing a silk scarf, even the lightest and thinnest fabric, is not something very practical in 30 degrees celsius weather. Do you agree, or do you still wear yours? Most Italian women don’t, unless they are going from ac to ac, and dressing up for a very special occasion.
Well, end of Summer is the perfect time to bring that beloved accessory back. And I even wrote an entire post on how to style a scarf like an Italian woman, not just around your neck.
Since now is the time to make the most of yours, go read this next: How To Style A Scarf Like An Italian Woman
I spotted a very similar look to one I shared in that post which I’d like to show you as my example. I love how the woman has layered it over the vest, which she is styling with tailored casual pants and a pair of sneakers. It just shows that practical travel outfits can be as chic as you want them to be. It’s all about the details, and the fit!
Wearing Light Knits, even Short Sleeved
What’s the first thing you reach for when the weather starts feeling a little chilly? For me, and many of my readers is short sleeve knits like these.
This is one of those pieces I suggest you invest in because it won’t only keep you warm but will also carry you from season to season. I wear mine under trench coats and blazer in Spring and Fall, and on their own at the beginning and end of Summer. And they also work great layered under chunky jumpers, maybe slightly itchy ones, during the colder months.
You can style this with any bottom, from jeans, to cigarette pants, midi skirts, and even pencil ones. You can even wear them with shorts for a very end of Summer look.
Here’s are two looks I spotted in Milan, and it shows us that our outfits can be very simple, but one detail alone can make them so unique. In this case, it’s the short knit’s bright yellow color. Outfit two is a little more simple bot the accessories really make it look well thought out.
Bringing Back Jeans and Denim
Are you one of those women who gets excited to wear jeans again after Summer? I definitely am, especially when it comes to my favorite pair of lightweight wide leg jeans. There’s something incredibly special about that little transition. It signals we’re nearly ready for the falling leaves, and the warm lattes.
It doesn’t have to be just denim pants though. Any type of denim fits here. It could be you’re dreaming of wearing that denim shirt. And that’s exactly the look I spotted in Milan.
Or you might swap your linen pants for a lighter colored jeans, and wear it like this Milanese woman did.
And don’t forget the denim skirt outfit I showed you earlier on.
Mixing Summer and Fall pieces
This is the simplest way to transition, similar to the act of layering a jumper over your shoulders, except here you’re actually wearing both pieces instead of just draping one over your shoulder. Think bermuda shorts paired with a long sleeve shirt, or a short Summer dress worn under a knit vest, no tights involved yet.
The look I spotted in Milan is exactly that last combination: a blazer worn over a short dress, with bare legs and no tights in sight. It’s such a small swap, but pairing a structured piece like a blazer with something as Summery as a bare-legged dress is what makes it read as transitional rather than fully cold-weather. Tights would have tipped it into Fall outright. Lleaving them off keeps it grounded in the season you’re still in.
Bringing a Few Fall Pieces Into Your Outfits
Whether it’s suede bags, light leather jackets, or a little bit of burgundy and dark tan — this is what most people do, and it’s for a good reason.
It smartly helps you to slowly transition your color palette into Fall and it also satisfies that urge of getting into your Fall wardrobe even when you still haven’t gone through your entire switchover.
This is why I want to end with seven outfits I spotted in Milan doing exactly this.
Having said that, not everyone suits warm Fall colors. If you’re not sure if you, here’s an easy way to discover it. Read this next: Simplified Color Analysis For Clothes + Steps To Do Yours
Going To Italy Soon?
End of Summer in Milan isn’t about overhauling your wardrobe overnight — these ten swaps prove that a few small, deliberate choices are enough to carry you from Summer into Fall while the heat is still hanging around.
I truly hope you found this post about end of Summer outfits useful. I really enjoyed doing the research and writing it. So thank you for reading my blog, as it gives me the opportunity to continue doing more of it.
One more thing if you’re traveling to Italy soon: unlike Summer, when it’s hot pretty much everywhere in the country, where you’re actually headed starts to matter a lot more this time of year, weather-wise. I’ve put together region-specific guides for exactly this — check out my What To Wear In Italy In September and What To Wear In Italy In October guides for more useful tips depending on where you’re going.
If you want to support me, please give this post a heart and share it with your friends who love fashion and personal style.
And don’t forget about the invitation I mentioned earlier to join Buona Settimana, my weekly newsletter that lands in your inbox every Sunday. See you there!
A presto,
Alessia
