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Known as the land of history, art, mouth-watering cuisine, and impeccable fashion, Italy truly is a dream travel destination. Whether you’re wandering through the ancient ruins of Rome, sailing along the Amalfi Coast, enjoying the beautiful rolling hills of Tuscany, or exploring Milan – the fashion capital of the country – dressing well is a fun way of elevating your vacation experience and making the most out of your time abroad.
It’s no secret that many Italian men have mastered the art of combining elegance, simplicity, and quality into their everyday attire. While there are certain regions where dressing up might make you stand out (rather than the other way around!), strolling through Italy seems like the perfect opportunity to feel like your best version and choose some nice pieces to accompany you.
Whether you’re dressing for the man in your life, or you’re a man who wants to elevate his vacation style, here, we’ll get into everything you need to know to put together classic, stylish looks for your Italian vacation, including some outfit inspo!
From understanding the essence of Italian fashion to packing efficiently for different seasons, I’ve got you covered. Consider this your ultimate guide to looking effortlessly chic and staying comfortable while enjoying la dolce vita.
What to Wear in Italy for Guys: Understanding Italian Style
Regardless of gender, Italian style is renowned for its elegance, effortless feel, and overarching simplicity. Clean lines, classic colors, and high-quality materials are some important key elements to take into consideration when putting together your packing list; from Merino wool for the colder times of year to linen for the warmer months, there are tons of great options out there to choose from.
It’s not about breaking the bank, either! Things like well-tailored trousers, well-fitted shirts, a good pair of loafers, and a nice watch go a long way in helping to bring together a ton of different mix-and-match looks. Understanding these basics is really all you need to put together your ideal packing list and look great during your time away.
Seasonal Packing Suggestions
Spring – late March to late June
If you’re planning to be in Italy during the Spring, get ready for mild temperatures and blooming landscapes. When it comes to weather, it’s always best to prepare for unpredictability, meaning layers are your friend.
For casual wear, think lightweight jackets, jeans, and cotton shirts. A classic white shirt paired with linen trousers, for example, is a great option for a day of sightseeing or a casual meal.
For dining out at nicer restaurants, opt for a dress shirt and tailored trousers with either loafers or dress shoes. In general, comfortable shoes are a must all-around, as you’ll likely be doing a lot of walking. Loafers, sneakers, or a good pair of sandals are all you need to switch up your looks and feel prepared for whatever occasion comes your way.
Essential Spring Picks
- Lightweight jackets and/or sweaters
- Cotton shirts
- Tailored trousers
- Linen shorts
- Comfortable shoes (loafers, sneakers, and sandals)
Summer – late June to late September
Summer in Italy can get famously hot, especially in southern regions and coastal towns. Breathable and airy fabrics like linen and cotton are your best bet! Not only do they keep you comfortable, they also look great.
A white linen shirt paired with neutral swimwear and sandals do the trick when you’re spending the day relaxing by the water – and don’t forget your sunglasses!
For evenings, a casual yet sophisticated look can be achieved with linen pants, a button-down, and a lightweight blazer if you feel the need for an added layer.
Essential Summer Picks
- Linen shirts
- Linen shorts
- Leather sandals
- Sunglasses
- Tailored trousers
- Button-down
Autumn – late September to late December
Autumn in Italy is all about layering! Like in any other season, the temperatures can vary, meaning having versatile options is key. For vineyard tours or walking around cities, think cozy sweaters over dress shirts and chinos. For wet or slightly colder weather, a trench coat or leather jacket can add a touch of sophistication and keep you warm during cooler days.
When you’re dressing for more formal dinners or evenings out, opt for a tailored blazer and dress pants.
Essential Autumn Picks
- Sweaters
- Dress shirts
- Chinos and dress pants
- Trench coat or leather jacket
- Loafers
Winter – late December to late March
Just like the summer can lead to incredibly hot days, winter in Italy can get quite chilly, especially if you find yourself in the northern regions and mountainous areas. A good, warm coat is essential, whether you’re hitting the slopes or just exploring what the region has to offer.
Thermal wear can be a great way of staying warm while still prioritizing style – not adding any bulk and being smart about layering are the real expert tricks here.
For walking city tours or casual outings during your trip, a combination of thermal layers, a wool sweater, and a warm coat works well. Once you find yourself inside restaurants and shops, it’s easy to remove your top layer and still feel comfortable.
Don’t forget scarves, gloves, and a stylish hat to complete your winter look (and keep your extremities warm!). During this time of year, boots are the most practical footwear choice, providing warmth, comfort, and style at the same time.
Essential Winter Picks
- Warm coat
- Thermal wear
- Wool sweaters
- Scarves and gloves
- Boots
Must-Have Items – For Any Season!
While it’s important to keep the season in mind before you get started on your packing list, certain items are universal and should be a part of your selection regardless of the weather.
High-quality closet staples like T-shirts, shorts, and trousers are the foundation of a versatile and functional wardrobe. Invest in pieces that are comfortable and durable!
In turn, accessories play a significant role in elevating your look; especially when it comes to traveling, bringing just a few of your favorite pieces can go a long way in upgrading even the simplest outfits into a stylish look.
Leather belts, watches, and hats can add a touch of instant polish and elegance to your ensemble. When choosing these items, opt for classic, adaptable colors that can be easily mixed and matched with the other pieces in your wardrobe.
Neutral colors like white, gray, ivory, navy, and beige are all popular choices for their undeniable versatility. A well-fitted blazer in a neutral color can be dressed up or down depending on the occasion. Likewise, a pair of navy, tailored trousers can effortlessly transition from day to night.
When it comes to footwear, sneakers, loafers, and a pair of sandals for those warmer months should cover all bases. If you have specific plans that call for formal shoes, make sure to bring those too!
At the end of the day, comfort is key during travel, especially when your itinerary includes lots of walking (as it probably will). Go for shoes with good support and, if you struggle with pain, consider bringing insoles for extra comfort.
Essential Year-Round Picks
- High-quality basics (T-shirts, button-downs, trousers)
- Neutral color blazer
- Dark tailored trousers
- Leather belt(s)
- Watch
- Sneakers, loafers, formal shoes (if needed)
What to Wear in Italy for Guys: Cultural Considerations
While it is important to note that not all regions in Italy are the same, Italian culture generally places a high value on appearance and dressing appropriately for different occasions. This norm can be seen enforced through different laws and possible fines (wearing swimwear and flip-flops away from the water in certain places can land you a fine of over $500!).
When visiting religious sites, for example, it’s important to follow the dress code for both men and women, which often includes covering shoulders and knees, as well as wearing shoes. While it’s possible that this dress code isn’t enforced in all churches, cathedrals, or similar sites, it’s still important to respect this rule and dress accordingly.
For men, this means staying away from sleeveless tank tops and short shorts for these visits, opting instead for linen pants in the summer and tailored trousers during the colder months.
Of course, the cultural norms surrounding clothing don’t only apply to specific religious sites, but extend to a restaurant experience, for example. Dining out in Italy often calls for a smart casual look; nicer restaurants may expect men to wear a collared shirt and tailored trousers (steer clear of shorts!). Generally, it’s a good rule to avoid overly casual clothes like basketball shorts and graphic tees.
General Do’s and Dont’s of Italian Fashion Etiquette
- Do dress neatly with well-fitted pieces and avoid overly casual attire in public spaces
- Don’t wear athletic wear – unless you’re working out!
- Do pay attention to small details like polished shoes and a well-groomed appearance, especially when attending a special dinner or event
Packing Tips
As we’ve seen so far, packing efficiently for your trip to Italy involves choosing versatile items that can be used to create a wide variety of different outfits.
To get started in actually planning and executing your ideal travel wardrobe, start by writing out everything that you’re bringing with you. Take into account the number of outfits you’ll need, the weather, and any special events or occasions you will attend, as well as other considerations specific to your plans (this may include things like swimwear or snow-appropriate attire).
Rolling your clothes, rather than folding them the way you normally would at home, can be a good way to save space and reduce wrinkles. While it might not be enough to rule out the need for an iron or a steamer upon arrival, certain pieces (like linen ones) are far easier to smooth out when properly & neatly packed.
For those who appreciate organization, packing cubes are another amazing hack to use when putting together your suitcase! If you plan on going shopping abroad, you might also want to think ahead and leave some extra room for your new pieces.
What to Wear in Italy for Guys: Outfit Inspiration
Here are some of my husband’s looks from our recent time in Italy! We were there in early June, meaning we were able to enjoy amazing average temperatures throughout our trip.
1. striped shirt + khaki shorts + sandals + watch + sunglasses
top (similar) | shorts (similar) | sandals | watch | sunglasses (similar)
This striped terry cloth shirt is a great way of bringing some visual interest to your look while still keeping things simple and classic. If you don’t plan on visiting any religious sites and are enjoying your time in the beautiful coastal towns of Italy, these 6’’ dock shorts are the perfect bottoms.
Flattering, modern, and timeless at the same time, these shorts pair well with a variety of different shirts – both solid and patterned – and make for a great casual but put-together piece.
A pair of good, comfortable leather sandals put you right into the vacation mood you are looking for, keeping your feet comfortable as you take a leisurely stroll and enjoy your day. Adjustable straps make it easy to get a secure, perfect fit.
To elevate your look in just a few seconds, opt for accessories like a watch and some sunglasses. Bringing a subtle but differentiating touch of polish to your look, these accessories make all of the difference in both the look and feel of your outfit.
Ideal for any day outing exploring, this look works beautifully for warm summer days!
2. white t-shirt + sweater + chinos + sunglasses + watch + loafers
shirt | sweater | pants | shoes | watch | sunglasses (similar)
For a nice dinner or even a special lunch, this outfit is the perfect choice. Effortlessly pairing these navy chinos with a simple white t-shirt, this look is as classic as it gets!
Using these versatile pieces, this outfit can also be easily transformed into tons of other variations throughout your trip.
On top, a linen-blend ribbed sweater is a great added layer for both warmth and style, adding a charming touch that seamlessly elevates.
These suede loafers introduce texture and an accent color to this outfit, bringing both balance and – you guessed it! – style to this overall look. Finish it all off with your favorite accessories, a classic watch, and sunglasses if you’re out during the day time.
3. white t-shirt + linen button-down + striped shorts + sandals + sunglasses + watch
t-shirt | button-down | shorts (similar) | sandals | watch | sunglasses (similar)
Spending your time relaxing by the water doesn’t mean leaving your personal style behind – on the contrary! It’s an amazing option to have fun with the pieces you choose.
These affordable shorts feature a great pattern that works perfectly with your best closet staples like this organic cotton white t-shirt, bringing character and charm into this simple, comfortable outfit.
On top, a linen-blend button-down provides a very lightweight extra layer that can both protect you from the sun and elevate your casual beach outfit into something more special.
For shoes, bring out your trusty leather sandals for comfort without compromising on the aesthetic! Finish it off with your accessories to pull it all together.
4. linen button down + linen shorts + sandals + watch + sunglasses
top | shorts (similar) | sandals | watch | sunglasses (similar)
This next look is the perfect example of how the right wardrobe pieces can seamlessly come together to formulate many different yet classic looks. Take your white linen-blend shirt, this time buttoned and worn with the sleeves rolled up for that perfect summer feel.
On the bottom, some navy linen-blend shorts keep you cool while also diversifying the sleek color palette of this outfit. As for shoes and accessories, you know the drill!
Bring out your leather sandals, watch, and sunglasses for a timeless look that will have you looking great and fitting right in (or standing out – in the best way).
Though we didn’t need to deal with cold weather, the principle of putting versatile and classic outfits together remains the same, regardless of the season. Finding interchangeable, timeless pieces is really all you need for amazing outfits and stress-free packing.
What to Wear in Italy for Guys: Bringing it All Together
Dressing well in Italy goes far beyond following the latest fashion trends; in fact, it doesn’t have to be about that at all! At the end of the day, it’s all about embracing a culture that values elegance, quality, and personal style.
Whether you’re visiting during the warm weather of summer or the cooler months of winter, there is an easy, functional, and stylish way to dress during your vacation.
By prioritizing comfort, versatility, and appropriateness for different occasions, you’ll be set to look and feel your best throughout all of the amazing things you have planned during your time away.
Now, if you’re a woman looking for Italian men’s fashion for your partner and now you want some ideas for yourself, here are 35 Italy Outfits That Are the Epitome of European Chic!
