How To Style A Denim Shirt Like An Italian Woman

We’ve seen how Italian women wear blue jeans, but what about a denim shirt?

Today, I’ll show you the same outfits I spotted in Milan, while sharing my style notes along the way.

So, if you’re about to grab yours for the transitional months, come take a look at how to style a denim shirt like an Italian woman. And don’t forget to add your own personal touch when you recreate these looks!

PS: If you want to know more about the personal style part, read this next:
How To Find Your Style & Dress More Like You

PS: This post includes affiliate links. If you click and purchase, I may receive a small commission at no extra cost to you. I only recommend products I have or would personally buy.

Pair It With Tailored Pieces For Work

I want to start with the least expected Italian style suggestion. If your work dress code allows it, try layering your denim shirt under your work outfits.

In the example from Milan, you can see the woman is doing it with a blazer and a short tailored skirt and heels. The combination shows personality but also femininity. The best part about it is that you have so much room for combining it with different colors and prints.

Here are more denim shirt + work outfit pairing ideas:

Under a full matching suit; you can wear it with heels or loafers.
With the classic pencil skirt and either flats or heels.
With wide leg pants and a cardigan.
Under a pullover worn with cigarette pants.
Under a knit vest and tailored pants.

Finishing Tips:

Make sure your denim shirt looks considered, though. These tips hold for most of the next style suggestions, but especially for work.

The right shade matters. The darker deeper colors tend to look dressier.
Avoid too many embellishments, embroidery, and too much distress.
Steam it.
Fit also matters, and you want it to fit you well, especially for an office outfit.
Button up the sleeves and the neckline to add more structure and make it more put together.

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Layer It Under A Coat

Whether you want to wear it this way for work, running errands, a travel day outfit, or any other fall or winter going out day, layering your denim shirt under a coat immediately gives a clear vibe to your outfit – structure and polish.

It also looks cold weather appropriate, tailored, and sophisticated depending on the rest of the outfit. This first look I spotted in Milan certainly does all of that, especially with those accessories.

The second look has a completely different aesthetic. The coat is shorter and the pants and shoe choice is less dressy. The baggy chunky look on the bottom paired with the more structured top says cool but put together. The woman could be going to work or university, or even just running errands. It’s clear that’s her style.

Wear It Under a Sweater

If you’re ready to wear your denim shirt but it’s too early for a coat, try layering yours under a sweater or a jumper.

This look might be a little warmer because of the thick cable knit sweater but it can work just as well under a thinner cashmere silk blend.

It’s the perfect example of what adding your personality to your outfit does. Every garment choice here is a personal style led decision, from the choice of a leather skirt, to the silhouette and length of that skirt, and the color pairings. And while that might be obvious, because every outfit involves several choices, it’s when you pair things slightly unexpectedly that your personality shines through the clothes you wear, and your clothes are no longer just clothes.

So if you like this outfit idea, don’t just stop there. You can swap the colors, add a print, change the leather for a different fabric, and play with your accessories.

Shop Medium-Wash Denim Shirts

Try Double Denim

You probably wouldn’t expect an Italian would tell you to try double denim. Yet, I have shared so many gorgeous double denim outfits from Milan, so I can’t not mention it in this post.

If you want to see those looks, check out this other style guide:
15 Blue Jeans Outfits From Milan – Effortless & Chic

When it comes to this, you can take it in different directions and wear it for different occasions. Let’s see how the four outfits I am about to show you do it.

Outfit one looks like an outfit you could wear on a cosy November day for the office.
Outfit two is very similar but a little more stylish, perfect for a shopping day or a cafe and errands kind of day.
Outfit three is ideal for both busy mums, women who love their casual comfy days but still want it to look intentional.
The last one is definitely growing on me, even though I don’t like the cowboy boots. Those colors are really stunning together.

Which one would you wear?

I’d choose outfit two but I would swap the mock neck for a white t-shirt or shirt, and the cowboy boots for brown loafers. I’d also be tempted to swap the color of the coat to black or even red.

Browse Dark Wash Denim Shirts

Swap A White Shirt For Your Denim One

Speaking of white shirts, the easiest way to wear more of your denim shirt this fall is to see how Italian women wear their white shirts, and try swapping it for a denim one.

You can start this fun exercise here: How To Style A White Shirt Like An Italian Woman

This swap immediately adds an interesting twist to an outfit, along with color and texture. It takes it from classic to a little more unique and quirky, but you can also make it edgy, feminine, colorful, with just a few changes.

Here’s what I mean. The outfit below was inspired by a woman in Milan wearing it with a classic white shirt. I honestly believe that the swap made the look so much better, less flat and boring, both in terms of color palette and also seasonality. This is the kind of outfit that fits right at the end of Summer or midway through Spring.

So, go ahead and find the look in that post I shared you love the most, and try it with a denim shirt instead. I think all of these looks have the potential to look stunning after that swap: 3, 4, 5, 6, 11, 13, and 17.

Wear A Lighter Wash For Spring

And as we’ve mentioned Spring, here’s are two great ways to wear your denim shirt:

Opt for a lighter wash
Wear it with lighter colors, like in the previous section and the next one. Don’t stop there – try it with white, pastels, and all your favorite lighter neutrals. But don’t be afraid to add some contrast, just like in the example below.

Pair It With Beige Pants (in Your Style)

Beige or khaki pants with a jeans shirt is a very common outfit among men, but us women can do it too. So, I wanted to show you how Italian women style it that way. I have two outfits to share, and they are both very different – both casual, but one is more classic (although still modern) while the other is cool and creative.

Love the Idea of a Belted Denim Shirt/Jacket?

Shop oversized denim shirt here and here

I’m certain most of you will be drawn towards look number one, and that happens to be a great inspiration for your travel days. Can you see how an outfit so casual (not only is there a denim shirt, but also sneakers!!) can look so curated and sophisticated?

Here are all the factors contributing to that:

The old money color palette helps.
The camouflage sneakers (hidden under the slightly wide leg pants and almost matching them)
The feminine silhouette of the denim shirt with that cinch in belt detail.
The way the woman is holding her bag, under her arms, is very chic which therefore gives that feel to the rest of the outfits.
And the tailored pants, of course.

More on the Italian Tailored Effect here:
Tailored Style Explained: The Italian Way To Dress Chic

Add Some Color

If beige and denim sound too boring for you, no worries, you can add some color. Here’s how Italian women do it, while still keeping it considered.

The woman in example one has layered it under a mustard light jacket. The cropped pants / long shorts also add more color to the outfit than if the pants reached the ankles. On top of that, we can see more color from the nail polish and the shoulder bag.

The second one is a broken double denim look because of the addition of a black jumper on top. So far everything is dark, but the color comes on top, and because it’s the first thing you see it’s enough to make it pop. The terracotta leather jacket, maroon boots, and tan bag are bringing that color. Of course, you could also swap that black jumper for a complementary color like green, or a neighboring warm hue like mustard.

If that’s too much, you can add color with your shoes, your bag, a neck scarf, or just the jumper. That works as well.

Try Styling It With Leather

My final style suggestion based on the outfits I spotted in Milan is to pair your denim shirt with leather. Black would be my first choice, but honestly, this eggplant plum color is stunning paired with the lighter shade of denim.

This is not the first outfit I share about the leather + denim combination, and each time it works so well. It especially does when you pair the right shade of blue with the right color of leather for your skintone.

If you have doubts about that, read this next:
Simplified Color Analysis For Clothes + Steps To Do Yours

Can you see the woman is wearing the outfit with sneakers?

That gives you another casual but elevated denim shirt outfit idea for fall, which shows it doesn’t have to be always a simple blue jeans and trench coat (although that’s gorgeous), and certainly not leggings and a sweatshirt, not if you want to dress like an Italian woman would.

Loving The Cozy Italian Style?

So, did I make you want to pull that denim shirt out of the closet a little earlier? I hope the outfits did.

In case you’re wondering which did it for me, it’s the coat look, but I’d need to do it with a different coat color, as that tan is not a good one for me. I am glad I didn’t pull the plug on that coat color before I learned about my color season. You can find yours with that color analysis guide I shared in the previous section.

Since I have given you plenty more to read along the way, I am going to share just one more that fits the seasonal cozy vibe of September, which is when I am writing this. Here it comes:

11 Ways Italian Women Wear Comfy Fall Outfits

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Thank you for reading and sharing.

A presto,
Alessia