Things People Always Ask Me About Italy: What To Wear?

I don’t need to say this because everyone already knows that fashion is incredibly important in Italy. I’ve noticed that Italian Fashion gives a lot of tourists noticable anxiety and whenever my friends or family come to visit they always send me at least one email asking, “What should I wear!?”

Your approach to fashion here will obviously depend on whether or not you want to outwardly display your nationality, or you want to blend in. Almost always, style is what tells everyone that you’re American (or foreign in general). It’s not the blonde hair or the blue eyes, it’s the patterned, purple floral dress that you’re rocking in April with your flip flops. Seriously.

Italian style varies depending on where you are, and a person’s particular style, though there are always some similarities. We’ll start with Florence because that’s where I live. First thing, get rid of all of your bright, bright colors. Don’t bring your floral dresses, your bright pink tank tops, or your bright purple sweaters unless your goals is to stand out immediately. Muted colors, natural colors, win in Florence. In the summer you’ll see a lot of Olive green, gray, and tan mixed with skinny jeans, and in the winter you won’t see anything but black, brown and gray (more or less). There is not a huge difference in age, people both twenty-five and fifty wear similar things. For example, my husbands mom is almost sixty and when she goes out she often wears skinny black slacks, high heeled ankle boots, a blouse, scarf, and peacoat. All black. In the night she’ll often wear a skin-tight cleavage showing, knee-length dress, high heels, and a little jacket to cover her arms.

Also, hugely in style is anything that is, “un po’ particolare,” which means a little particular. A sweater with buttons running up the side, an asymetrical shirt, anything that is “particular” or “a little strange” is often good. Badly fitting jeans, a t-shirt, and running shoes are never stylish, not even if you’re sixty.

And remember, layers, layers, layers, even in the summer, and make sure your bag matches your shoes. Yes, I’m serious. Yes, people do pay attention to that. I don’t know why. Stop yelling at me!

A  casual summer outfit for a woman in 20’s and 30’s might look like this: 


Short shorts, slouchy boots, oversized blouse, sweater, scarf, big sunglasses.


Light denim skinny jeans, white sneakers (or leather sandals), long, flowy shirt, scarf, huge sunglasses.

Notice how no skin is showing, I'm not wearing any bright colors, and I appear to be high.

Notice how no skin is showing, I’m not wearing any bright colors, and I appear to be high.

People do not wear flip flops unless they are at a pool. They do not go bare armed or legged until June/July (wear tights under your shorts and with dresses). You also won’t see women wearing tight tank tops and booty shorts. Even in the middle of summer, people often cover their arms (including men), with a cardigan, or light jacket.


Tight skinny jeans, high heels (always, ALWAYS bring a pair of ballet flats with you in your purse), stylish blouse. If you hate heels you can wear a stylish flat shoe that is not a running shoe. I know that we Americans love our comfortable running shoes but leave them at home next to your treadmill.

Summer For Men:

Leave your basketball attire at home, you don’t need to be “prepared” for sports here. Leave your jerseys and your basketball shorts, and basketball shoes, actually, you know what? Burn that shit. Go shopping, and buy yourself something that says, “sexy 007 agent,” then, pack some fitted t-shirts, a cardigan, a scarf, and jeans that do not fall off of your ass. Bring some loafers and converse which are always fashionable here in the summer, or any other stylish sneaker that is not a running shoe. p.s. I fucking hate white running shoes on everyone. Even on old people.  They make your feet look massive and for some reason remind me of moon excursions or dentistry.

Winter For Men:

Bring a shirt with a collar, a v-neck sweater to go over it, and slacks for dinner. In the day, fitted jeans that do not fall off of your ass, a sweater (not a sweatshirt), scarf, and a black coat. Suede shoes, black boots, or dress shoes are worn both day and night. Yes, I’m serious.

If you are a visual person and you want more ideas you can visit some examples here: Awesome clothes I pinned on pinterest. 

37 thoughts on “Things People Always Ask Me About Italy: What To Wear?

  1. The only thing that makes me sad about this is that while I have appropriate clothing set aside for my trip… I discounted my RED pea coat. Guess I need to get the pockets fixed on my brown leather Kenneth Cole coat before I leave after all…

  2. Everything in the dress code your wrote is so true. I was always amazed at the ladies wearing the skinny five inch heels on the uneven streets of Rome. My feet were killing me after a couple hours and I had on thick heel boots. I miss Italy.

    • It took me two years to learn how to walk in high heels on the streets. I think that the secret is slow movements. Italian people walk very slowly (if they are having a stroll at night) whereas we Americans run. If you walk as slowly as possible it works. Unless you’re drunk, then you just fall a lot and look like an idiot (which is basically most days for me).

  3. i’m touring Italy with my school this April and am trying to figure out what to pack! i’m going from Milan to Venice to Florence to Siena to Assisi to Rome to Pompeii then back to Rome before going home! I also live in Rhode Island so i’m kinda use to cold weather, Help!

    • I would pack as light as humanly possible. Start by going to your local LUSH store and buy their toothy tabs toothpaste, their shampoo and conditioner bars and a body bar, and body lotion bar. It sounds nuts but trust me, your life will be easier only traveling with solids (and their products are awesome). It’s the only stuff I ever use when I travel because it’s so much easier and nicer.

      The second thing is bring:
      Slippers (marble flooring is freezing).
      Comfortable flat boots that can be worn in the evening.
      Comfortable day shoes of whatever your style or preference (but nobody wears running shoes unless they are running, heads up. Ankle boots will be best in April cause it rains a lot).
      Cardigan. Cute coat. Cute scarves. One dress for evening. Tights. Leggins or skinny jeans. One sweater. And t-shirts. Bring things that all match each other. Black and neutrals are always “in” in Italy. Bright pinks and pastels are not.

      I just wrote a post about how to dress for spring students. Check that out, too.🙂 It might help. Also, give up on curling irons and straighteners. The humidy in April will make it almost impossible for your hair to hold anything anyway. Women don’t go hair crazy in Italy anyhow, hair is normally worn naturally.

      The WORST thing you can do is overpack. You’ll be miserable. It’s not a “hauling things around” friendly country. Back light.

  4. I’m going to Italy (Rome/Venice/Milan) in February and I’m not sure what to pack because I heard it’s wet and cold. Plus I come from Singapore so I’m not used to the cold weather. Please help!

    • Annie, yes, it’s very humid and chilly that time of year. Pack a lot of clothes that can be layered. At night you’ll need a sweater and a coat. Boots are best because it does rain a lot that time of year. An umbrella is a must. Pack for cold rainy weather. But, sometimes it can be sunny during the day so make sure you bring a few lighter day outfits just in case. Black is the usual color in the winter in Italy. Everyone wears dark colors and tons of black. But of course you can wear whatever you like.

  5. I’m rather depressed after reading this… I’m a quite colorful person, so this is bad news for me :))
    I somehow expected to be more freedom and colour in Italy.
    I’ll be visiting Florence… sooo… I guess my patterned leggings… Lime green dress… (not neon, and lightweight, flowy cotton, so, while not transparent at all, not 100% opaque either so the colour doesn’t make your eyes twist haha) or colorful-with-citrus-fruits-pattern sneakers have no place there? :)) (all of those not together lol!)
    But aren’t you melting if all your skin is covered (in may) ? Is short sleeve ok in may? What about tank tops?
    sorry for the questions bombardment :))

    • Hello love! You can totally wear whatever you want! Florentines wear color in the summer but, usually, they’ll only wear one bright thing with other things less colorful like black. Short sleeves and tank tops are fine but they don’t wear the super skin right ones. Usually very loose shirts, often layered and over-sized, with leggins or shorts.🙂

      • Oh! That’s perfect then!😀 Chillax-loose shirts / blouses / tops are my jam!
        I was already picturing myself looking like a neon sign in a sea of grey and brown hahaha :)) Now I feel better :))
        Thank you so so much for the reply & advice!

  6. I’m African American and when I travel I usually wear my hair in sengalese twists or cornrowed in the front and wavy hair weaved in. I have lots of black clothing, but I will definitely stand out. I’m also 57 so I will be wearing comfortable loafers/flats, any tips for me to know to avoid any problems?

      • Ah! Well, if I’m being honest there is still some racism in Italy but it’s related more to nationality than skin color. They’re very anti immigrants right now. But, if you’re from the US or a first world country people will be warm and friendly. Except for the people who hate Americans. They’re assholes to everyone. Most Italians are decent people though, just like anywhere.

  7. My partner and 12 year old son will be going to Italy this May. We are flying into Rome from Toronto and then going to Sorrento, Venice, Cinque Terre and Florence. We’re in our early 50’s and high heels are not something I even wear at home. I wear a lot of tights with loose shirts/tops and I was going to wear my comfy yet dressy sandals (flat), but I guess I should also pack a closed shoe? Now for Amalfi Coast and Cinque Terre I was going to pack running shoes or Keen’s (sandals) for hiking. Is that too “Canadian?” And can you get away with wearing shorts there as well? Weather wise I imagine it can be fairly warm in mid to late May? Thankfully, I have a lot of black and gray clothes🙂

    • In May shorts are totally fine. The locals will usually still wear shorts with tights under until June. I’d recommend a closed shoe of some kind because it can still be quite rainy inMay and your poor feet will get soaked. If you have ankle high boots, or booties, I’d bring them. They’ll keep your feet much more dry than sneakers. For amalfi coast running shoes are totally fine. Again though, depends on the weather. Italy can be rainy til June. Sneakers will soak your feet. There are a lot of hills though so sneakers will be the most comfortable.😉

  8. Hi M.E.!

    I am going to be in Italy in late May and I am wondering if bringing my Louis Vuitton bag is a good idea or not. They are my go to bags, cross body or back pack, I’m torn. We are going to be going to the typical tourist spots but are staying in 5 star hotels.

  9. I will be traveling to Italy in July 2016. I don’t want to stand out as an American. Can you tell me the current trends this summer for jeans (skinny, cropped? both?) dresses (daytime), sandals (type), flats (ballet?)? Are neutral colors still recommended? I plan to travel very light. I am in my 50’s and like to dress stylish (classic styles) and chic (not “old” but at the same time age appropriate)

  10. Will be in Italy for a few weeks May/June. My husband and I are in our early mid 50’s and we will be traveling with our two college aged girls. We will be in Rome, Positano, Portofino, Venice and Florence and surrounding areas. What are your suggestions for packing light (very hard for me to do), yet fashionable?

    I have seen conflicting information regarding shoes/boots/sneakers, shorts, jeans/no jeans, dress pants, skirts, dresses, short sleeves/sleeveless,etc. I live in the midwest and go from boot/booties to open toed shoes. My girls wear birkenstocks or sneakers for walking. They also wear shorter shorts. We will be walking A LOT!

    So, what does one wear during the day vs evening? . Need a packing list and as much info as possible! :)!

    • The days are much more casual than the evenings. Fashion also differs greatly between each city and every individual person. With that being said, it really just comes down to making an effort. Short shorts and Birkenstocks are fine for the girls for the day. In evenings, they’ll want to bring a few dresses. Zara is always a great place to start since A LOT of Italians shop there. It’s a super popular store in Italy. Your husband will want to check out Zara as well. And, he should bring at least one nice shirt or two for evening with some lightweight casual slacks. T-shirts (or like a cute pollo) and shorts are fine for the day. Black is always a fashionable color in Italy for evening for everyone. You’ll want to bring a few cute dresses for evening with a pair of walkable nice shoes (booties are perfect). May is still chilly at night in Florence and Venice. I go with booties in the evening with simple black dresses and during the day jeans with comfortable leather flats or converse with a lot of layers. It will be warm but frequently cool and rainy during that time. I’ll put together a post for you with some examples.🙂

    • Oh, and for your girls, Italian women often don’t go Bare legged until June/July. Also it will be a little chilly in May. It’s popular to wear tights under shorts. Make sure they layer a lot. Skinny jeans might be more ideal for May.

  11. This is such an awesome post & so glad i found it. We leave this Friday for Naples/Sorrento/Rome/Amalfi Coast. Can’t wait and your post has really helped so thank you!🙂

  12. So happy I found your blog. We will be in Venice, Florence and Rome the last two weeks of September. Will white skinny jeans be ok or will it be better to wear black? Thanks so much for any advice.

    • White jeans or colored jeans (green, salmon, red) are always fashionable in the summer months. However, Italy can be a little rough on white pants. Wine, pasta sauce, etc. So maybe throw a tide pen or something in your purse in case of a minor accident.😉

  13. Hello. So glad I stumbled upon this post while doing a search on “what to wear in Italy”. My friend and I will be the last week of March. I see that it can be chilly with sunny days and possible rain? Your opinion on what to pack for end of March? We will be in Venice,Florence and Rome. Thank you

  14. Oh my goodness, I’m so excited to go to Italy and during the summer! I’m a teenager but I love fashion and I’m going with my equally stylish European and American mom so I’m pumped! Although I love heels and can walk in there anywhere, I sprained my ankle, and my doctor recommended only sneakers no flats. I want to look stylish but I don’t know what to do? And I also I’m really self conscious about my short hair, I recently had it shaved and I’m not sure if it’s a real cultural norm. Any advice about what to do about shoes and hair covers?

  15. Hello,I haven’t read any posts referencing the weather in the Fall, specifally late Sept/Oct. We are landing in Rome then heading south. Will it be too warm for short boots? Or too cool for a dress?
    Thank you.

    • September and October are usually warm in the day but cool at night. They wear short boots all summer😉 Dresses should be fine. Keep in mind that they don’t wear super short or super tight dresses unless they’re going clubbing. Also, shorts should be fine but being black tights to wear under them if it cools down.🙂

  16. Hi…. Great site! What do yo suggest for the end of Sept. to the middle of Oct. for traveling between Venice, Florence, Orvieto and Rome? I was planning on bringing the following in black.. 1 pair of capris, 2 black slacks, 1 black dress. Warmer colored different tops for alone or layering, a jean jacket and a couple cardigans. Scarves/shawls/ lots of accessories. Do I need to bring a black rain/trench coat? Am I on the right track?
    Appreciate your advice?
    Thanks, Jody

  17. Hi. I have been invited to a “drinks/cocktail party” “casual attire” event. What should I wear? Are pants ok or should I wear a dress? Thank you.

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