Today, we’re doing something a little different.
Rather than just showing you denim shirt outfits for men I spotted in Milan, I’m mixing those with a few ways I’d style them myself, for my husband or for you.
All are very Italian and put together, but in a more effortless way. The idea: outfits for a man who likes classic and modern mixed together, and wants comfortable smart casual pieces for weekends, travel, and everything in between.
Table of Contents
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Shop Italian-Style Denim Shirts
10 Ways To Wear A Denim Shirt Like An Italian Man
Let’s get straight into the outfit ideas. I will make a note for those that I spotted in Milan under the image.
1. Wear It Under A Blazer
All of the outfits I spotted in Milan, except for one, followed this exact formula. So if you love your blazers, smart casual tailored Italian style, or want an idea to dress up your denim shirt, start here.
There are so many ways you could do it. So, even if you’re thinking that a blazer is too dressy, there are some outfits that are actually not. Have a look.
I’d say only the last outfit feels a little dressier, even if it features the double denim look. And that’s mainly because of the dark color palette and the dressier brown loafers.
If you look at the other three outfits, the shoes are all on the casual side. And that’s the first detail that’s going to help dress down your blazer and denim shirt outfit.
The first outfit is great for Spring, or even the end of Summer. The color palette is very old money Summer but in a realistic approachable way. If you’d like to dress this one a little more, just swap the shoes for a nicer pair of leather loafers – brown or navy.
The second one with the tweed blazer is perfect for fall. It’s also great if you have a more casual and slightly rugged style. This can be your dressier outfit. It’s still double denim, but it’s nice enough for a dressier meeting, a date, or anywhere you want to look more put together but still yourself.
Outfit three is the most casual because of the sneakers, but the dressier blazer, worn buttoned up balances the shoes beautifully. I get that this look is not for everyone, but it’s likely for you if you’re someone who wears blazers every day, and wants to wear them a little more casually over the weekend or on a leisure trip.
Finally, the last look is a great idea if you love double denim, and want to try dressing it up with a blazer, perhaps for date night, but also for a business meeting, provided it’s a more creative casual situation.
Here’s a bonus idea that just came to my mind as I write this:
If you like more creative and modern outfits, try wearing a denim shirt under a suit with a smart casual shoe, like a loafer or even a less dressy oxford shoe. I would skip the tie for this one, but feel free to try it anyway.
2. Try a Denim Shirt with a Tie
I know I just told you to skip the tie but this is different. You’re not wearing a blazer here, and this outfit formula has an intellectual and quirky vibe. It’s smart, but a little colorful. It includes tailoring and classic pieces with a few unique details, like the contrast between the colors and the print on the tie.
This is smart enough for an office or a daytime date night, and definitely perfect if you’re your own boss and want to dress up.
The key here is to create contrast and to play with the tie, but it also needs to tie together with the outfit.
3. Pair It with Baggy Pants
If your style leans towards a more cool Milanese guy, this is probably the one you’ll feel most comfortable copying. All you have to do is contrast your denim shirt with a pair of black baggy pants, and pair it with a cool pair of sneakers, or even vintage ones. The two styles really go well together.
The shirt worn over the trousers rather than tucked in is perfect here. Though, I’ve seen cool Milanese guys with their shirts (denim and not) tucked in too. The key is to opt for more oversized shirts and to wear them layered over a tshirt.
4. Style Your Denim Shirt with Tailored Pants
We’ve already seen these in many of the looks I’ve already shared, but I’d like to emphasize it, because it’s the easiest way you can style your denim shirt like an Italian.
It might not be the most popular way to wear it in Milan, but it surely is the easiest to recreate.
Here’s why: for this formula you don’t need a blazer. All you need is a nice pair of tailored pants, which you likely have, and if you don’t, here’s one that’s very Italian.
Of course, you’ll need the right pair of shoes, and a belt or not, depending on the style of the pants.
You can choose to layer a white or a black tshirt, if you’re going for black pants, but of course black is not the only color option. You can do white, sand, even mocha, khaki, and brown; any color you like will likely go with the right shade of denim shirt.
Why is this very Italian?
It’s simple. It’s because the tailored pants, and the dressier shoes (even loafers), add that touch of tailoring that balances the more casual denim shirt.
As to how to wear it, you can tuck it or not, but it will give you a different effect. It’s also important the fit and length of the jeans shirt goes with the fit of the pants.
PS: Have you noticed how this and the previous outfit have the exact same color palette but look completely different? That’s what style and fit can do to an outfit, so don’t overlook those details.
5. Layer It Under a Mac Coat
Are you thinking what I am thinking? The outfit is nearly the same, again. It is. But also, it’s not.
The fit of the trousers, the shoes, the style of the shirt, and the styling are completely different. And those aspects create a different outfit.
What I want to emphasize here is that you can take an outfit you normally wear – black pants with a dark denim shirt, and add a mac coat to change it up completely. It dresses it up, it gives it a very seasonal (mostly fall) vibe, and it feels very London and Milan.
You can do the same with a different style of jacket or coat, but the effect will also be different.
6. Denim Shirt and Suede Jacket
And that’s precisely the example I’d like to give you. While the previous outfit was a modern classic Milanese look, this is more classic Italian with the suede jacket. It’s no longer black and denim, as we’ve moved to navy pants and shoes.
This should give you another idea. If you always dress up your denim shirt with a pair of black pants, try navy trousers instead.
Also, if you only have one darker denim shirt, buy a second one in a lighter wash, and perhaps also a third one in a lighter fabric. You’ll find all these options below and linked in the edit at the beginning of this post.
Shop Light wash denim shirt
Shop Cotton denim shirt
7. Try It with White Pants
If you want to turn the black and denim shirt outfit into the perfect Summer look, swap the black pants for white. I would suggest opting for pants and not jeans, as I don’t think the double denim works as well with white jeans. It loses the classic old money gentleman vibe.
Focus on nailing the accessories. Dark deep browns give a very quiet luxury Italian vibe, whereas sand shoes create a more modern effortless feel.
While this is perfect for the Italian riviera – think Trieste, Portofino, Genoa, it’s as good for the city.
8. Style It Under a Pullover or Sweater
Italians love wearing their shirts under a cashmere knit, for fall and Winter. They wear them on their own, under a blazer, a jacket, and even a coat.
This is the idea I am suggesting, but instead of a regular blue or white shirt, you can wear your denim shirt.
That’s going to add a more unique vibe, more contrast and color, and also make the outfit less classic, which I know many men appreciate.
You can see two different outfit ideas below, one with just a v neck sweater, and the other with a pullover and blazer. They have different styles, but they both work.
Which one do you like best?
I personally prefer number one, because number 2 is a little too classic for my taste, but it all depends on your style.
9. Add an Over the Shoulder Sweater
If you take outfit formula 4 and add an over the shoulder sweater, the result is an outfit that feels even more Italian, but also a little preppy.
It’s really that simple, but it’s important to nail the color palette.
You don’t want to go too matchy matchy with your sweater, but you equally want it to go with the look.
In the example, we’re seeing a tan sweater. It’s a neutral that goes with all the other colors, but it’s also close to the cream trousers, and in the same color family as brown. But it also contrasts beautifully against the dark denim shirt, so it’s a win win.
10. Layer It Under a Cardigan
Finally, if you have a more casual cosy style, you can also layer your jeans shirt under a cardigan. I like the zipper style this has, but buttons would also work.
This outfit feels intentional, put together, but comfortable enough for a long day at work. It’s great for the office but also a teacher position, and you can always wear a mac coat or a parka over it.
More Italian Men Fashion
There you have it, 10 Italian-style outfit ideas with denim shirts for men.
So, did you find one or two to copy?
If you’d like more outfit ideas, with jeans or something else, you can continue your search below:
Men’s Jeans Outfits Italians Actually Wear
The Italian Guide To Mens Loafers
Fall Outfits For Men You’ll See In Milan (Casual To Smart Casual)
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A presto,
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