Whether you’re going to Italy this fall or simply switching up your seasonal wardrobe, and trying to think of outfits you can actually wear, this guide is for you.
I’ve put together 14 fall outfits for men all seen in Milan to give you plenty of ideas to work with. All of these are casual to smart casual. Just keep in mind that they represent the type of casual that works in Italy.
What this means for you is that it might be a little smarter than what you’re used to, but that’s a good thing. It’s going to push you to keep dressing better. After all, what’s the point in putting in the effort if it doesn’t result in better outfits?
If you love any of these looks, you’ll also find options to shop them.
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14 Fall Outfits For Men To Try This Season
Here they are, broken down by piece, so you can find exactly the look you’re after.
White Pants
Let’s start with white pants. Although the rule of not wearing white pants beyond Spring and Summer is no longer a thing in Italy, you’ll find less and less people wear them during the Winter months. If you also like avoiding white pants this time of the year, it makes sense to get your last wear out before it starts raining and getting muddy.
The three I spotted in Milan are all smart with a casual Italian feel, the kind that feels polished but relaxed. They are also very different.
The first feels a little more classic, even old money, though the palette is a touch brighter than the classic one. It’s the type of shades I’d imagine an Italian would wear on the riviera, but it works as well in the city. You can wear it on a date or for a smart casual work situation.
Outfit two is the one which feels the most old money. It also presents that signature Italian no-sock style, which I know can be a hit or miss with men. So if you like this outfit enough to recreate a similar one, don’t let that small detail stop you. You can wear a sock or longer pants.
Outfit three has a very dapper Roman vibe. If you lean towards that more casual modern Italian man style that Romans do well, and don’t really feel at home in classic old money outfits, this might be the perfect way to smarten your white pants. Wear them with a matching blazer and t-shirt. The fit is key here. The blazer needs to be double-breasted, fit well, but not tight, and needs to be buttoned.
Fall note: What makes these three outfits perfect for fall? They are perfectly layered, and they showcase how fall outfits, especially when the season has just begun, don’t need to fit within the standard color palette. Longer sleeves, layering, and contrast are a good starting point.
Shop White Jeans
Jeans Outfits
Let’s talk about jeans now. Have a look at the three outfits I chose to share with you because they have that fall vibe you’re looking for. Two of these feature a brown outerwear layer. This gives you the perfect example on how you can introduce fall colors in small doses.
Outfit one is pairing a brown blazer with a pumpkin-colored tshirt, and while those colors are very autumnal, this outfit doesn’t feel like a cliché ’. I think it’s thanks to both the lighter shade of denim and the fit of the clothes. Again, I can see the style leans more towards the Roman man style as opposed to the classic Milanese.
Outfit two is a little more casual than the usual Italian men style, but not all Italian men like wearing tailored pants all the time. This is an outfit they might wear to travel or on a relaxed day out. The layering, the color pairing, and the fit of the outfit still feels considered.
The third one looks like a double denim moment, but it’s not. Do you like it?
More Italian men jeans outfits: Men’s Jeans Outfits Italians Actually Wear
Shop Brown Fall Jackets
Suede and Corduroy
If you’re asking yourself which pieces you should invest in that feel seasonal but not obnoxiously so, consider these two fabrics.
The best part is that if you invest in these now, you can keep wearing them throughout Winter, and depending on their color, likely also in Spring.
Italians love them this time of the year.
Here are four great examples.
The first one is a full-on corduroy suit in a classic camel. It’s the only suit I am showing you today because it fits the smart casual dress code. It doesn’t feel too dressy, and it’s the combination of the fabric, the colors and that roll neck that tones it down. So, if you have a fall occasion you need to dress for (not a wedding, unless it’s really casual), maybe this could be the way to dress for that. Feel free to change the color palette.
The next outfit has a cooler vibe, and this one fits both the Roman and Milanese cool men style. It’s also the perfect example of how to wear all brown. The jacket is the corduroy piece here.
This is the classic old-style Italian man outfit you’d wear to work that doesn’t feature a suit, and not even a blazer. It’s the perfect office outfit, but of course, you can make it work outside the office too, if you like this classic polished style. The jacket is the suede piece.
Finally, there’s this outfit featuring a pair of taupe corduroy pants. They are styled with a white shirt and a cream leather jacket. This outfit fits the old money palette beautifully, and if the cream leather jacket feels a little old, try a waterproof one. Whether it’s a bomber style or a square cut, it gives you that smarter look while keeping it practical.
Leather Jackets
If you’re wondering how to wear a leather jacket in a cool, casual way, these outfits fit that vibe. The jackets are also very different, so if you still haven’t invested in one, or are looking to buy a second one, this will help you understand which way to go. Do you like the vintage one (the boxy brown one) or the one that feels a little more contemporary and minimalist (the blazer style)?
Both looks show sneakers and elements of tailoring. Look one includes a shirt, while look two includes tailored pants. Both have a second piece that feels a little more casual – the relaxed-fit trousers in the first and the t-shirt in the second. They are great examples on how to dress casually with a little more intention.
Shackets and Jumpers
A shacket is not the most Italian thing, but modern Italian men are embracing it. Here’s how they style it.
I couldn’t end this men’s fall outfits post without mentioning jumpers. You know Italian men love them for layering, and there’s no better season to do it. If you like that style and want to give it a go, these outfits either include a jumper or could easily take one, if layered properly. I am referring to outfit two under the white pants section and outfit three under suede and corduroy.
The jumper outfit I’d like to show you caught my eye for its simplicity, but it somehow works. It’s a simple jumper worn over the shoulder, almost like a scarf, over a very basic office outfit. That might even be a uniform.
More Italian Men’s Guides
And there you have it, the 14 fall outfits for men I promised you with my usual commentary, which is meant to get your imagination going. The point is for you to run with it, and that’s how you create outfits that make you feel good, comfortable, and handsome.
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Italian Outfits For Men That Always Look Good
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Thank you so much for reading.
A presto,
Alessia
