Looking for outfit ideas to wear right now? You’re in the right place.
Hi, I’m Alessia — founder and writer of Italy with an Italian.
Today, I’m kicking off a new series on Italian street style, where I’ll share real looks Italians are wearing this season — mostly women, sometimes men too.
These outfits are meant to inspire your current wardrobe and help you capture that easy Italian style. You can always save your favorites to recreate later.
If you enjoy this first post, give it a heart and share it with a friend — that way, I’ll know you’d love to see more of these!
Let the inspiration roll.
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Table of Contents
What’s Trending in Italy Right Now?
Before I start sharing the looks, I’d like to tell you what seems to be trending right now on Italian streets.
I have never seen so much double denim, and it’s not only tourists who are wearing it!
In terms of color palettes, the most obvious include camel, greens, greys, white, and one of the Pantone colors for next year – a golden, mustard pastel shade. You can find more about that in this post – Italian Spring Summer 2026 Fashion Trends.
Surprisingly, I haven’t seen as much burgundy, but it might still be early for those deeper richer reds.
Tan was the most popular color of shoes and accessories, along with deep browns, and the usual black and beige.
Speaking of shoes, Italians have started wearing their boots, and very few are still wearing sandals. Of course, I am referring to streets from the fashion capital. Things will likely be different if you take a look at what people are wearing in Amalfi or Taormina. Although, I hear that the Amalfi Coast has been particularly cooler this season.
Italian Street Style: 25 Outfit Ideas To Copy
The outfits that follow include a mix of current seasonal outfits that caught my eye for different reasons. Some are unique, others are classics done really well. I will also share one I didn’t like as much. The looks are mostly women’s outfits, but I will also sprinkle a few men’s ones.
Enjoy!
Transitional Outfits for October
I am starting with the most appropriate outfits for this time of the year. These are perfect, if you like me, live somewhere where fall feels more like the end of Summer rather than the beginning of Winter.
The first one is perfect if you are not ready to say goodbye to your favorite white Summer dress. You can wear it under a blazer, cinch it with a dark brown belt, and pair it with dark brown shoes and a matching purse. It’s a classic look with a touch of edge thanks to the belt over the blazer.
Are you still wearing short sleeves and not ready to say goodbye to your favorite yellow pieces? I love this romantic look with the puffy A line skirt, and a matching short sleeve knit.
However, what I think makes it stand out are the accessories. The white loafers and the darker yellow bag dress it down beautifully, making it a great morning outfit to wear, especially if you like that more feminine romantic vibe.
I already mentioned how I saw a lot of white on Italian streets this month, especially trousers. Here’s a great example on how to style white so it feels fall-appropriate. Add a classic khaki trench coat, and pair it with a pin striped white and green shirt to tie in the look. Because the latter is not your usual pin striped shirt color, it makes the outfit immediately more interesting.
Take a look at this classic man’s outfit. It features classic pieces and an equally timeless color palette. However, the lighter fabrics paired with a slightly higher trousers crop give this look a very end of Summer feel.
This next one is perfect for the office but also a night out with friends. A classic black pencil skirt, paired with a white camisole, and all black accessories. The piece that makes it feel and look transitional is that light fabric and light colored pin striped blazer. It might be linen.
I must say this is not an outfit I would wear myself. It feels a little too masculine and I don’t personally like those trousers. However, I think the colors and pattern combination work really well.
Let me remind you that this post is about me sharing real outfits from Italian streets, so you can practice spotting what you like and don’t like, and choose the looks you want to inspire you. It’s also a great example of how to make an outfit look more masculine, if that’s your vibe.
Here’s how Italian men are wearing white trousers this season. It’s very transitional, paired with a dusty blue tshirt, and a casual navy blue jacket. Three clothing pieces plus a pair of beautiful shoes create a classic smart casual look that’s very Italian but also so easy to recreate. Feel free to share it with your partner. He can always switch the colors!
Let’s see how men are wearing burgundy during fall. I love how this gentleman paired it with black trousers and a classic white tshirt. The black shoes, dark brown belt, keep the look classic but that jacket brings a unique touch that feels seasonal, but not overdone.
How Italians Are Wearing Leather This Fall
Something else I saw a lot of but forgot to share it above is leather. Italians love wearing leather in Fall and Winter, but it’s usually easier done in the transitional months, because let’s face it – leather isn’t the best outerwear fabric for staying warm.
In this case, the lady was wearing black leather wide leg long bermuda shorts. She paired it with a cream high neck knit and a checked black and white blazer. I think she also nailed the accessories, black low heeled boots, and a bright orange purse to inject a little color; after all, it’s pumpkin season!
Leather on leather is not a look I would have thought I’d love this much, yet it’s done impeccably. It’s the silhouette and tailoring of the two main pieces that make it look so beautiful. Also the fact that the leather is different but still pairs beautifully shows that this outfit was well thought out. The taupe knit and beige pumps pair well without overwhelming the final outfit.
Here’s one of the few burgundy outfits I saw, considering this is one of the most popular colors of this season. It’s simple, casual, yet chic. I love how that peplum style leather jacket adds a lot of femininity to a rather masculine piece. It’s even more stunning when combined with that beautiful rich color.
If you think leather jackets are not feminine enough for your closet, perhaps you need to find a peplum leather jacket in that style and color.
Calling all the older ladies that think they can’t wear bright colors. Of course you can! Look at how this woman is doing it. You can do the same with orange, yellow, pink, blue, red, etc. Starting with an all black outfit will ease you into wearing some color, and maybe that’s all your classic style needs.
Speaking of pumpkin season, this lady nailed this outfit. She added a seasonal pop of color with those tailored trousers, and then styled the rest in a very classic way – a white button up shirt, dark brown flats, and a matching leather jacket. I love the more casual style of the jacket and how she then added the darker orange purse. Stunning! Could this be your halloween outfit to go into the office?
On that note, I have been wanting a dark brown leather jacket for a while, and I have recently spotted one. I’ll let you know if I end up buying it. Stunning! Could this be your halloween outfit to go into the office?
As I promised you at the beginning, I wanted to share a look that I didn’t like as much. The outfit is not completely wrong, but I don’t like the leggings situation, even though the tonal look helps.
The thing that sends me bananas are those furry loafer mules. You can’t see much of them in that picture but when the shoes were touching the ground, so was the fur. I find that extremely gross, and the same thing applies to any trousers that skim the ground. I mean let the spazzino (street sweeper) do his work!
Fall Blazer Outfits From Milan
This older gentleman’s outfit made me smile, because it reminded me how it’s not just Italian women that know how to dress, but every gender and every age. If you were to switch those trousers to darker navy blue, and those button up shirt and socks to lighter blue, the outfit would still work but it would have less personality. This man clearly loves blue and he’s not afraid to pair different shades together, tying it all in with that classic more formal checked blazer.
Would you like to recreate a double denim look but don’t think you can go that far? If so, have a look at this outfit. It’s a pair of jeans paired with a denim blue colored blazer. The culotte style jeans give the look the perfect transitional vibe and those bright blue pumps add that unique touch to the outfit, while keeping it tonal.
Here’s a more masculine meets Milan cool girl blazer look. The colors are super classic, and so are the fabrics and brown leather shoes. But the oversized fit of the blazer and the baggier trousers make the look feel more modern and slightly edgy. Also, the slightly more open shirt’s neckline gives it a more relaxed vibe.
If you are a man who loves combining smart and casual, you are going to love this outfit. And if you are a woman you might want to share this one with your husband. It’s a great weekend look for those men who want to dress up but still add that personal touch to their outfits.
If you were to remove that maroon red quilted gilet, that outfit would be perfect for the office or a dinner out. Yet, by adding that single piece you immediately make the outfit feel more day appropriate, so much so that you could even wear it to go pick a Christmas tree, provided it’s not too cold.
How Italians Are Wearing Coats
Considering how many layers she is wearing, I’d say this lady must really dislike feeling cold. Nonetheless, she looks stunning. Khaki tailors cropped trousers, a white button up shirt tucked, a classic brown tweed blazer, and an even more classic camel coat over the shoulders.
She accessorised her outfit with simple brown shoes, a classic canvas beige and brown designer bag, and added a little more personality with that pistachio green silk neck scarf. Would you wear this look?
Speaking of adding personality to your outfits, this is definitely one way to do it. Not everyone loves animal print, not everyone would wear this much, so if you do, go ahead and wear more of it! However, keep the rest very classy to balance the bold look that that print creates. This is such a great example on how to do it tastefully.
Another classic outfit with a pop of seasonal color. However, look at it carefully. Do you agree that that neckline and lapel checked detail elevates the look so much? Imagine the same look with an all black trench coat. It would still look nice but it would not have the same level of personality and uniqueness.
Here’s an outfit that I would add to my fall uniform looks. The colors work beautifully, the styling is kept so classic and minimalist, yet the silhouette of each piece is perfection, and those colors are not as popular as if you were to switch the jeans to darker blue and the trench to beige. Do you agree?
Here’s a more unique way to style two denim pieces together – add some animal print. It could be in the form of a coat like the woman styled it, or you could do it with your shoes or purse. Either way it works.
This is probably one of my favorite looks of this bunch. I love the tan accessories paired with that lighter shade of jeans, and that checked trench coat is fantastic. That’s a great way to add some personality to your outfits.
I know a beige trench coat is a classic and much more versatile piece, but if you are someone who loves wearing this style of coats, you might as well invest in a more unique style. Of course, the idea is to keep everything else simple and classic, so that the unique piece can shine without feeling too much.
More Seasonal Italian Fashion
So, how did you like this first post of the Italian street style series?
Remember, to give this post a heart and share it with a friend, if you’d like this series to continue. That shows me you like it. Thank you so much.
Until I write the second post, here are more current Italian fashion posts you can read during your next coffee/tea break.
What To Wear In Italy In November
What To Wear In Italy In Winter
Italian Christmas Outfit Ideas
Before you go, I’d like to invite you to join my newsletter – Buona Settimana. I send one weekly email every Sunday. It’s like having a chat with an Italian friend, where we talk about food (I share my favorite recipes), fashion, travel, and life. You can join via one of the sign up boxes in this post. I hope to see you on Sunday.
Ciao,
Alessia
