How to Dress Like an Italian: Fall and Winter Edition

Slim fit jacket, hat and booties (Photo: Nicoletta Reggio of the Italian fashion blog Scent of Obsession).
Slim fit jacket, hat and booties (Photo: Nicoletta Reggio of the Italian fashion blog Scent of Obsession).
Sunglasses, leather jacket and neutral colors on Scent of Obsession‘s Nicoletta Reggio

Sunglasses, leather jacket and neutral colors on Scent of Obsession‘s Nicoletta Reggio: the perfect Italian autumn look

Fashion in Italy is serious business—so it’s no surprise that lots of travelers often ask us how to dress like an Italian while they’re here! While you certainly don’t have to dress like a local when you’re visiting, and while you should definitely wear what you’re comfortable in, immersing yourself in the culture can be part of the fun. And that means dressing (and shopping!) like the locals do.

In the fall and winter, the Italian dress code entails bundling up with lots of layers. In fact, one thing foreigners often comment on is how Italians often start wearing heavier clothing around October, regardless of whether the weather’s actually still quite warm and mild… simply because it’s time for the cambio di stagione (change of seasons)!

When dressing for the weather, remember that the climate varies depending on where you’re going. It’ll be relatively mild in Naples and the south, getting colder as you head north—and it’s often downright bone-chilling in the dead of winter in Milan.

Here are our top tips for effortlessly chic Italian style for both men and women in the colder months. And for the most up-to-date Italian fashions, don’t forget to check out our Italian style page on Pinterest!

(Coming in the spring instead? Here’s our guide to Italian fashion in spring!).

Pile on the neutral colors

What to wear in Italy

Jeans and a sweater is a great casual, but fashionable, look

Classic neutrals like black, gray, brown and camel pop up more than usual in the colder months; you’ll also see Italians using these neutrals as a background for a “pop” of a bolder, darker color, like burgundy or forest green.

Meanwhile, the “no white after Labor Day” rule in Italy doesn’t exist: Locals love winter white, especially for jeans and sweaters.

Jeans can be chic—but colored pants are popular, too.

In Italy, jeans are popular. They’re considered a bit on the casual side, but as elsewhere, a beautifully-fitting pair of jeans can always be dressed up with great boots or heels, a nice blouse, and layered jewelry, which is a combination you’ll see on many Italian women.

Men, too, wear jeans, although it’s generally seen as a more informal way to dress, and not something you’ll see most men wearing while they’re out to a nice dinner or elegant drinks.

As much as you’ll see blue and gray denim washes in Italy, you’ll also see lots of colors. Colored trousers remain popular throughout the fall and winter months, with colors ranging from dark green to taupe.

Don’t leave home without your sunglasses

That’s right: Sunglasses are all the rage, even in the winter! Italians don’t leave home without a pair of stylish pair of large, dark sunglasses, a great way to pull any outfit together… and add a level of glamorous mystery.

Think timeless outerwear: a trench or blazer when the weather’s warmer, a classic overcoat when it cools down

Italian fashion in winter

Stylish men in the streets of Florence. Photo by TRÈS BIEN (Flickr)

When the weather’s crisp, but not freezing, try out a timeless trench coat, blazer or khaki jacket. (Tailoring always is key!). As the temperatures dip more, pack a slim-cut tailored overcoat (Italians can be spotted in both single- and double-breasted coats); a more recent trend has been a down jacket with a fur-lined hood, a great way to keep toasty when it’s freezing!

Italian fashion in winter

Classic jackets on a rainy day in Venice. Photo by Robert Trm (Flickr)

Don’t go anywhere without your leather or suede boots (or booties)

Best of Italian fashion in winter

The perfect winter Italian look: a slim-fit jacket, hat, colored pants and booties (Photo: Nicoletta Reggio of the Italian fashion blog Scent of Obsession).

Italian women love their sky-high heels… but we understand that not everyone walks gracefully in them on cobblestoned streets! To blend in without sacrificing comfort, look for leather and suede boots and shoes. For women, a variety of styles, from heeled, knee-high boots to riding boots, are popular. (For that extra European touch, wear your boots over your pants, the better to show off that beautiful leather!). This season, short, stitched leather booties, paired with pants, are also very trendy at the moment.

Remember to be sure to pack a pair of waterproof or water-resistant shoes, too. You won’t want to have to run back to the hotel to change during snowy and rainy days!

Pile on the accessories, especially a beautiful bag and scarf

A carry-all bag is a must for travelers—and to blend in with the locals, try a large leather cross-body or shoulder bag for a daytime look. That advice goes for not only women, but men! Italian men aren’t afraid to carry a small bag or briefcase during the day to store items like cameras and books. (Fanny packs are rarely used in Italy, and even backpacks are usually used by students only).

Hats, scarves and gloves not only add a cozy and sophisticated touch to any look, but also help you keep warm with fabrics like wool and cashmere. A pair of well-fitting leather gloves lend elegance to any outfit. Don’t be afraid to  try all three together for a stylish, and functional, look on a cold day.

Finally, pile on the jewelry to spice up any outfit with both subtle and statement pieces, like gold or gemstones.

What are your must-haves for stylish travel in Italy? Let us know in the comments!

54 Comments

  • sandra says:

    I love all your tips! I wish we dressed more like this in So Cal.

    • Rekasharma says:

      I am unable to read articles online very often, but I’m glad I did today. It is a nicely informative article in fashion, traditional & costume jewelry ranges, I have ever read. Thank you.

  • Sam says:

    Fanny packs are pretty common in the Veneto region. I see them all over the place.

  • Isabelle says:

    I was in Italy for 2 weeks in September and found your fashion advice spot on. The women, young and old, all dressed beautifully and had gorgeous hairstyles. Any idea where I can look for photos of Italian hairstyles for women so I can get my hair styled like them? An internet search wasn’t much help

  • Grace says:

    What does one dress for in the middle of September in Naples- summer or autumn? Do we dust the boots and bring them along?

    • Walks of Italy says:

      Ciao Grace, we think it may be a bit too warm for boots in September in Naples. Bring lots of layers as it tends to be warm during the day and cool at night. Buon viaggio!

  • Barbra says:

    What about Rome in mid-October?

    • Walks of Italy says:

      Ciao Barbra, weather in Rome in the fall tends to vary, so we’d suggest packing layers from t-shirts to sweaters and a light jacket. Let us know if you have any questions!

  • Louise says:

    We are going to Italy Sept 8 – 20th and are wondering what to wear, will it still be summer. We are going to Florence, Sorrento & Rome.

    • Walks of Italy says:

      Ciao Louise, the weather is still quite warm in September, especially in Southern Italy. We suggest packing lots of layers (skirts, pants, sweaters, short sleeve tops, etc.) as it tends to get cooler in the evening. Let us know if you have any questions!

  • Elizabeth says:

    I will be in Rome from the end of November until mid December. What is the weather like and how should I dress? I have heard it is rainy and around 45 degrees Fahrenheit.

    • Walks of Italy says:

      Ciao Elizabeth, weather tends to vary throughout the fall and winter from warm, sunny days to rain. We suggest packing lots of layers (scarves, sweaters, t-shirts, hats, etc.), a warm coat and boots. Let us know if you have any questions!

  • Donna says:

    Hello! I will be in Venice, and Pordenone area end of September and 1st week of October- what do you suggest that I take for casual dress? Will be sightseeing and casual dining. Thank you!

    • Walks of Italy says:

      Ciao Donna! We definitely suggest lots of warm layers and waterproof jacket and shoes as weather tends to vary during that time between rainy and sunny. Let us know if you have any questions 🙂

  • Juu says:

    Dear sir

    We be going to Italy, in feb traveling from Rome, from south to north Italy covering most of the major city’s.
    We be doing lots of walking & sight seeing.
    I prefer to wear a good running shoe but afraid it might look bad fashion. Is it better to wear my booty.
    As for winter jacket, can I wear a bright pink short down in Italy? Will the color be too stricking ? Or prefer black down .
    Over all, is down jacket common in Italy during winter.
    Thank you

    • Walks of Italy says:

      Ciao! Fashionable running shoes are in season this year, and you may also want to bring your boots if they’re comfortable. Down jackets are in fashion each winter, and we think your pink coat should be just fine. Let us know if you have any questions!

  • Anita says:

    Hello there 🙂 I will be in Rome from the 11th of October and then to Florence a week later. To say I am excited, would be an understatement!
    I am in a quandary over clothes. I plan to invest in a beautiful burgundy leather jacket from Massimo Dutti. Would that be over the top? Also, I love wearing dresses, would it be okay to wear dresses with stockings? Is it a fashion faux pa?

    • Walks of Italy says:

      Ciao Anita! The leather jacket sounds fabulous, and wearing dresses with stockings is not a faux pa as long as it is not too warm outside. Buon viaggio and let us know if you have any questions!

  • Olivia says:

    I will be studying abroad in Florence from late January to the middle of May. Any tips of specific items of clothing to bring? I see there are a lot of layers. Thanks!

  • This is so far the best site that promotes womens fashion online in UK. Designer clothes are so much in demand nowadays. There are many people who will love your website.

  • S says:

    Are riding boots/knee high leather boots out of trend there right now?

    • Walks of Italy says:

      Hi S, definitely not! Some classic styles are here to stay and many women still wear knee high leather boots to protect their feet from a lot of walking and inclement weather!

  • I am sure that after following your tips, any one can dress like Italian.

  • Jane says:

    I will be in Milan, Florence & Rome from Sep 13-16, 16-23, and 23-27, respectively. Would it be okay to start wearing ankle boots there in September? I’m also planning to bring ballet flats and low-heeled sandals for warmer days. Also, what about fedoras? Thanks!

    • Walks of Italy says:

      Hi Jane,

      All of those things sound ok! Italians wear ankle boots practically year round, but by September it’s common practice. That said, it all depends on the weather – September can still be quite warm in Rome and Florence, so other options like your ballet flats are perfect. Also, we’re ok with fedoras 🙂

  • Very good tips for how to wear the latest fashions.

  • Laurelle says:

    I am from Papua New Guinea (literally the tropics) and will be in Italy from the 11th to 27th of December visiting most major cities. Which places or areas in Rome can I do some winter shopping as soon as I arrive?

    • Walks of Italy says:

      Hi Laurelle,

      Rome is filled with shops in every corner and December is a great time to go to get the best winter clothes. For designer clothes, you’ll want Piazza di Spagna, which is filled with designers like Prada, Dolce & Gabbana, Missoni, Versace, as well as Chanel, Louis Vuitton, Jimmy Choo – the list seems endless! For more reasonable prices (though not necessarily cheap) you can go to Via Cola di Rienzo (via means street in Italian), the commercial heart of the Prati neighborhood just north of the Vatican. Otherwise head to Via Nazionale, connecting piazza della Repubblica and largo Magnanapoli, which has plenty of shops where you can shop on a budget and get more value for your money. Have a great trip!

  • Melissa Wells says:

    We are going to Europe on October 26th and will be in Italy a few times between going to other countries. We will be going to the opera in Italy and would like to how one would dress for that in winter?

    • Walks of Italy says:

      Hi Melissa,

      Opera dress code is formal wear, especially in theaters like La Scala in Milan. To get a feel for how formal the opera house you’re going to is, check out its website beforehand. We agree that it’s more difficult in winter, but a pair of thick tights and a long, elegant coat can solve most problems. Inside you can wear a long-sleeved dress or carry a shawl or scarf to cover your arms. The opera in Italy is worth the work!

  • eileen espinoza says:

    I am going to Italy in the end of December how is the weather then and any tips on how to dress?

    • Walks of Italy says:

      Hi Eileen,

      The weather in December completely depends on where in Italy you will be. While the north of Italy will be cold, likely with snow, the south can stay relatively warm all year. Some years in Sicily they take a dip in the sea after Christmas lunch! In any case, we suggest bringing a comfortable pair of boots and a winter coat.

  • Paige says:

    Hello! I will be studying abroad in Florence from the beginning of September to the end of April, and I was wondering what kind of coat I should be getting. Should I be more focused on warmth or water resistance? Thanks!

    • Walks of Italy says:

      Hi Paige,

      It’s hard to say. While Florence tends to stay a bit warmer, the winter can still be quite chilly and some winters it might even snow! That said, it also tends to rain in the autumn and winter. We’d suggest getting a good, warm winter coat and purchasing a sturdy umbrella once you get to Florence!

  • Heather says:

    Hello! Do you have any advice for what to pack for a trip to Naples and the Amalfi coast in early October?
    My research indicates that it will probably still be warm (70s Degree F), but I wanted to double check before I begin my packing list. Should I bring long sleeve shirts or focus on short sleeves with a cardigan? I’m try to fit everything into a carry-on size suitcase so I want to pack light. Also, are there specific colors I should stay away from so I won’t stick out a lot? Right now I have a mixture of all black, all indigo/dark blue, all purple, and one turquoise shirt I was thinking of packing, plus 2 pants, and maybe one skirt. Do you think it would still be too hot for boots? I would appreciate any advice! Thank you!

    • Walks of Italy says:

      Hi Heather,

      Your research seems right to us! While it is still warm in October, the mornings and evenings can get a bit chilly. The best thing to do is to pack similar colors and things you can layer, so that you can mix and match and add or take off items as the day warms up. Italians love boots and you’ll likely see them already in October, but whether or not you’ll be too warm for them depends on how easily hot or cold you are! A pair of low cut boots might be perfect. Let us know if you have any other questions!

  • Lisa says:

    Hello,

    I’m confused as to what to wear for my trip to Europe in late October 2015 till the middle of November 2015.

    I’ll be in Paris from Oct 20th for 7 days, Venice & Rome till November 1st and London and Barcelona till November 15th.

    Can you please help me on what to pack & what to wear in Paris, Venice, Rome, London & Spain? I love your tips! It’s so very helpful!

    Thanks in advance,
    Lisa

    • Walks of Italy says:

      Hi Lisa,

      Unfortunately we’re only experts of Italy, so we can’t advise you on Paris, London or Spain. November is a great time to visit for lower prices and fewer crowds, but it’s also Italy’s rainy season. We recommend bringing warm clothes, impermeable boots and buying an umbrella when you arrive!

  • Rosina Ricci says:

    Fashion in Italy means a lot of things, but as the title suggests, quality, elegance, comfort, and fantasy are its four cornerstones. Without any kind of accessories and designer clothes fashion is incomplete. Italy has a reputation for creating fashion. Italians often start wearing heavier clothing around November. They also prefer sweaters and a light jacket in winter.I always contact to Dressspace for my winter clothes and stylish dresses, they provide me pretty and gorgeous coats, sweaters and dresses at an affordable price

  • Laura Wise says:

    While I’ve never been to Italy, I have been to other parts of Europe. I think as Americans we have this mindset that every Italian we’ll ever encounter in our visit is going to be like all the models on the runway, when in reality, Italians are not that much different than Americans. Except they don’t wear their pajamas or worst attire out in public.

    I leave for Florence next week and plan to dress in neutrals (black, grey, dark green, navy, white) in simple yet trendy pieces. I’ll be wearing a khaki trench coat, so that should hide anything that might be a potential fashion crisis.

    My biggest issue with clothing myself for this trip hasn’t been the clothes, but the shoes. I am down to the wire with deciding on shoes and I am on the fence about my choices. I purchased this pair of New Balance 580 a few weeks back: http://s7d5.scene7.com/is/image/NB/wrt580xb_nb_34_i?$dw_temp_hero_gallery$ What do you think? Too light colored and sporty? I tried them on with my trench coat and honestly didn’t like the combination too much. I am debating on a different pair on the more navy or black color scheme. My next issue is with a black pair of shoes. I have one pair of black flats that I’ve had for years and they’ve sort of stretched out over time, but I think they’ll still do the trick, if I need them. I am considering taking a pair of black Dankso clogs (opened back with a heel strap). How does that sound? Do Italians wear clogs/Dansko, or will I look goofy? I’m beginning to believe that I could honestly wear clown shoes and no one would care, since the moment I open my mouth, they’ll know instantly that I am a tourist (if my blonde hair and blue eyes don’t give that away enough)! Haha! Any tips would be helpful! Thanks!

    • Walks of Italy says:

      Hi Laura,

      You’re right, in many smaller towns Italians dress just as we would – sometimes even in sweatpants! This article is simply for those that would like their clothes to “fit in” while in Italy. That said, the idea of the bella figura exists, and a tourist is more likely to be well received if they’re dressed like they respect themselves. It seems like you have that down! As for shoes, take whatever pair you like the most that are also comfortable. However, we wouldn’t suggest a pair of clogs in November, the weather can be cold and/or wet! Have a great trip!

  • Bianca says:

    For Laura. Blonde hair and blue eyes in north italy are commons. I’ m italian and i’ m blonde like all in my family. My son are blonde and his eyes are blue. We are not in Africa

  • Me says:

    Hi, thanks for this article, it helped me a lot to figure what’s better to pack! I’ll be studying in Milan from September to March, and I’ve already packed several jackets, long-sleeved shirts, and leather boots since I’ve heard it gets pretty cold in the north. Can I also use ballerina flats or is it too cold to use them in the fall? I’ve also packed jeans for comfort, specially for attending classes. I was wondering if I should take my white jeans too or if Italians never wear them for fall/winter? Same for white sneakers (Converse), do Italians use them? Also, this might be kind of a silly question but I was wondering if Italians celebrate Halloween like they do in America, getting dressed up in costumes and stuff, since I have an unused Halloween costume I couldn’t use last year and I would like to use it this year. Thank you so much for your help!

    • Walks of Italy says:

      Hi,

      Great choices so far! Italians love Converse sneakers and you’ll see them everywhere, so that’s a great option to pack and comfortable for all the walking you’ll be doing. September is usually still quite warm, so a pair of ballerina flats is perfectly fine, though you probably won’t use them much past October. White jeans is up to you, but the Milanese tend toward dark colors, especially as the weather gets colder.

      Halloween isn’t officially celebrated in Italy, but you can find many parties or clubs to go to for the event and find a mixed of dressed-up and not dressed up. Here the Halloween costumes still tend toward the scary, as Carnival (usually in February or March) is their time to dress in any style of costume. Hope that helps!

  • Alison says:

    What kind of boots do you recommend? Are combat boots in style?

    • Walks of Italy says:

      Hi Alison,

      We recommend whatever boots you’re most comfortable after a lot of walking! That said, boot fashion in Italy ranges from classic leather tall boots, suede booties and yes, big black combat boots. Hope this helps!

  • Monica says:

    We will be in Rome the first of Nov. 2017. Being from TX ,we love our beautiful leather western style boots. Would these be too much?

    • Walks of Italy says:

      Hi Monica,

      America’s beautiful Western style hasn’t hit Italy much, but our philosophy is to dress comfortable and confident while traveling! Maybe you’ll start a trend 🙂

  • Sarah says:

    I’m planing to visit Italy in the near future, thanks for giving me heads up on the fashion and style statement of the Italians now i’ll pack my bags according to the month i will be going.

Leave a Reply

Your email address will not be published. Required fields are marked *