As the temperatures get warmer, it’s a clear sign that summer is just around the corner. Before you know it, you’ll be reaching for shorts instead of pants or jeans.
Chances are, you’ve already started doing so… and that’s probably what brought you here, looking for shorts outfits for men.
Hello, and welcome. I’m Alessia, the writer and founder behind Italy with an Italian.
If you’ve been on a style journey—trying to elevate your everyday outfits and maybe taking inspiration from Italian style—you might be wondering whether wearing shorts is actually a good idea.
In this post, we’re answering that question. I’ll also share 14 shorts outfits that tick all the right boxes:
✔ inspired by Italian style
✔ easy and comfortable, perfect for hot days
✔ put together without feeling overdressed.
Table of Contents
14 Shorts Outfits for Men (And How to Wear Them Well)
Let me share the first four outfit ideas. Have a look and see what stands out to you.
Do you agree that all of them feel dressed up, even the last one that’s the most casual of all four?
What do you think makes them feel and look that way?
When it comes to the first three outfits, it’s like we’ve taken a tailored outfit and chopped the pants into shorts. Can you see it?
That’s the power of tailored style, even when you’re not wearing a suit. You can read more about that here.
If you like what you see, here’s how to recreate it.
How to make your shorts outfits look more tailored:
- Choose tailored shorts, bermuda style, longer, with central pleats
- Make sure they fit well, not tight and not too oversized.
- You can go with both thicker pants fabrics, and linen.
- Add a belt, and a pair of dressier shoes, like loafers. Ideally, you want to match the color and fabric of the two.
- Wear them with a shirt or a polo shirt. Roll up the sleeves, for that very Italian vibe.
- Make sure every item is clean, pressed, and looks high-quality.
- Add a nice watch and a pair of sunglasses.
- Follow a classic color palette for that very old money, refined style.
Shorts Outfits For The Evenings
If you want shorts outfit ideas for dinner time, outfit three above is one of my favorites. Let me share four more.
Outfit three feels the most casual of them all because of the footwear choice. I would advise on swapping it for loafers, especially for the evening. However, if you’re having a very casual evening by the sea, it can still work.
On the other hand, this last outfit is the most dressy. I am still not sure how I feel about styling a blazer with shorts for men, but this outfit does look good, and it could be a good way to add a layer when it might get chilli in the evening.
But it’s only a look I would advise for a coastal, seaside luxury holiday. Wearing a shorts and blazer in the city wouldn’t make much sense in my opinion.
Men’s Shorts Looks For Different Styles
In this last section, I want to show you how you can dress up shorts and make them feel put together, while also keeping in line with your preferred style. Let’s see them.
Body conscious
If you’re someone who works hard in the gym, and wants your outfits to showcase that, this is the only outfit in this post that feels a little more fitting. I personally don’t like that look, but this is still doing it elegantly. The shorts are not too short, and the tshirt is not too tight.
Casual & Cool
If you prefer a more casual cool style, you likely want to wear jeans shorts. Here’s how I would imagine a young Milanese man wearing them for a relaxed night out in the cool Navigli area. There’s the casual element, but the shirt and that nice classic watch give this look a more curated feel.
Roman Man Shorts Look
You’ve likely noticed how Roman style is a lot different than Milanese. The latter is more elegant and curated, while in Rome, Italians tend to dress a little more relaxed while still ticking the key Italian style boxes.
This is an outfit I can see a Roman or even Southern Italian man wear in Summer, when he wants to look good without trying too hard. I’d prefer it if that shirt had one more button done up. I don’t like a man that shows too much chest; I find that tacky. But other than that, this outfit could be a great in between look, not too casual and not too dressy.
Preppy The Italian Way
Shorts outfits have the potential to feel very preppy when done right. In this last section, I want to show you a few ways to combine that style with the Italian aesthetic.
What makes these look preppy?
- The lighter color palette, as well as the white and dark nautical-style pairing.
- The pin-stripes give a preppy vibe.
- Pairing shorts with a long sleeve knit, or an open shirt it’s very coastal preppy, and can also feel old money.
- The fabric choice does that too – I am referring to the linen shorts and the crochet polo.
The fit, the tailored elements, and the loafers give these looks that Italian aesthetic we know and love.
Should You Pack Shorts For Italy or Europe?
Let’s start by answering the most common question about shorts and Italian style.
Do Italians wear shorts?
The correct answer is yes and no.
Shorts are more common in Southern Italy, but it all depends on the location and the occasions. For instance, you won’t find Sicilians wearing shorts to the office.
If we look at Milan’s streets, you’ll realize that almost no Milanese men are wearing them in the city. The people wearing shorts are tourists – either foreigners or Southern Italians on vacation.
So, what should you do if visiting Italy?
Should you wear shorts in Italy?
It depends on where you are going, your style, and whether you want to blend in or just feel comfortable.
Start by asking yourself these questions:
- do you want to look like a tourist or a local?
- Do you want to prioritize comfort or how you look?
Even if you answered b to both, that doesn’t mean you can’t wear shorts!
Here’s my opinion as an Italian.
Wearing shorts in Summer In Italy
If you are going to Italy on vacation between mid June and end of August, there’s nothing wrong with packing a pair of shorts. And that holds independently of whether you’re vising Sicily or Milan.
Outside that period, shorts are unnecessary, and wearing them will definitely make you stand out for the wrong reasons.
Shorts in the evening (yay or nay?)
Did you notice I said pack a pair of shorts, not just shorts? That’s precisely the point. Even if you are visiting Italy in the hottest months of the year, you should still pack one or two pairs of pants.
Pants are more suitable for dinner time, especially if you are staying in a fancy hotel or dining at an upscale restaurant, or just want to make the extra effort to look the part, whether that’s to please your partner or to impress the ladies. Ultimately, I say do it for you, because when you know you look good, that boost of confidence makes you enjoy yourself even more.
Where are shorts not allowed in Italy?
The only place I know of is the Vatican, including Saint Peter’s Basilica and the museums. However, many upscale restaurants might also not allow shorts, or might let you in, but you’ll feel very out of place wearing them. That’s why it’s best to put that extra effort when getting dressed.
About wearing shorts in the morning..
When it comes to the morning time, or maybe more casual evenings, I say you can absolutely rock those shorts and look sharp in them, even in Milan.
If Milanese don’t feel right wearing them I cannot blame them. They are likely working, or living their Milanese life, and shorts might not make sense for them.
But that’s different for you, if you’re on vacation and not on a business trip. The important is that you style them in a way that makes you look good, put together, most importantly not sloppy. And that’s precisely what the outfits we saw above can do for you. Just follow the tips I’ve already shared and you will be fine.
What about the rest of Europe?
While Italy, especially the North, is more well known for its sense of style, the same holds for other fashion capitals, including Paris, London, Stockholm, and Copenhagen. I would also add Berlin, Barcelona, and Madrid.
As someone who has travelled extensively through Europe I can tell you that when it comes to wearing shorts, the same holds for Europe. But, again, it all depends on the type of trip you are taking.
If it’s a fun beach holiday, you’ll need a pair of pants or two for dinner time.
If you’re based in a city, you could absolutely wear pants all day every day and be completely fine. After all, isn’t it the top you are wearing the most important part of a hot day outfit. Nail that, in terms of the fabric and colors you wear, and you will feel comfortable.
If you’re here, I can tell you care about the way you look, so your best way forward is to make sure you pack a mix of comfortable, breathing outfits that look put together, including both shorts and pants.
Does my husband wear shorts in Italy or Europe?
I thought answering this question might be really helpful and confirm what I just preached.
My husband rarely wears shorts outside the house. When he does, it’s usually a very hot or casual day. He’s either dressing them up with a shirt and a nice pair of shoes, or keeping it casual with a tshirt and pair of sneakers, especially if he is running errands or maybe washing the car. But that probably happens once every Summer.
If we’re traveling in Italy or within Europe, he only wears shorts in the morning if we are staying somewhere next to the sea. He still makes the effort to dress up his shorts. And in the evening, he wears pants.
If we’re taking a Summer city break, the only shorts outfits coming with us are casual shorts sets that feel like elevated loungewear and are perfect for the airport. He’s usually wearing one set on our way there, and there’s a second set inside his suitcase.
That’s as simple as that!
More Italian Men Style Guides
If you enjoyed the inspiration and tips I shared here, you’ll find more guides below:
Italian Outfits For Men That Always Look Good
Men’s Wedding Guest Outfits For Every Dress Code
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A presto,
Alessia
