If you are planning to visit the Cathedral and the weather is hot - think of taking some light shirt that does not take much room in your bag: you will need one at the entrance of the Cathedral as people are not allowed inside with bare shoulder.
Toiletries and Medical Supplies: Pretty much anything can be purchased in Milan upon arrival.
Miscellaneous: Take your ATM card - there are many cash machines, so your card will not let you down.
SUMMER Milan is very humid in the summer so try to take as many cotton or 'breatheable' clothes as possible.
Toiletries and Medical Supplies: Strong deodorant!!! The tubes and the buses tend to pong in the summer, so dont add to it!
I would reccomend bringin industrial supplies of mosquito reppellant, Milan is renowned for the mosquitos, especially in the Navigli area. In fact most of the restaurants and bars stock their own but dont risk it - these beasties are monsters and dont take any prisoners!
WARM clothes!! and layers, they dont seem to understand central heating, as they keep it so hot you feel like melting whereas outside it is so cold you feel like it is entering in your bones!
also remember if you really want to fit in you will have to bring a pair of shades, even if it is Winter!!
An UMBRELLA is the most important thing to bring to this town- The weather is changing all the time - and its raining a lot!
Comfortable walking shoes are a must - the has to be a lot of walking in this city, mainly because of the shopping but also because its faster to get around by foot in the area around the walking street Corso Vittorio Emanuele.
Bring with you a lot of money, above all, if you're a woman and like shopping. Does anyone know a woman who doesn't like it? Uhmm, rethoric question, indeed.
Well, as you know, , near the Duomo ,and to be more precise, in the so called 'Quadrilatero d'oro=Golden Quadrilateral' --Via Montenapoleone, Via Manzoni, Via della Spiga and Via S. Andrea-- there are the showrooms of the most important Italian stylists such as: Armani, Coveri, Versace, Krizia. An ideal place for your shopping, isn't it?
Luggage and bags:
Bring luggage that has wheels! And if you can, try not to bring too much. In other words, if you want to SAVE money, by NOT taking a taxi from/to Malpensa airport (like i HAD to), bring bags that you are able to carry alone. Money will be saved by leaving form Cadorna train station, and taking the Malpensa express for 45 minutes right to the airport! Trust me....i could have purchased two new pairs of shoes with the money i spent on taxis!*****Make sure that you don't forget to bring a good-sized backpack (for those NON-backpackers) for weekend getaways from the city.
Clothing/Shoes/Weather Gear: SHOES....hmm...I don't understand how women in heels do not sprain their ankles every single day!??!?! The sidewalks are NOT pedestrian friendly! In that case, wear comfortable, and FLAT shoes. otherwise, take great caution in heels!
UMBRELLA!!! Start out brining a cheap one. Then, depending on how long you are staying, you will need to buy another cheap umbrella after the first one breaks! Don't worry, as soon as it rains, there are umbrella vendors on every street corner!
Toiletries and Medical Supplies: Italy is not a third world country, so don't feel lik eyou have to bring everythign from home. They have shampoos....although conditioners seem harder to find. As for medication, bring your tylenol/asprin/advil from home, it's just easier this way. Pharmacies in Italy are very different than in Canada; everything is pretty much behind the counter, which to me was very annoying.
Photo Equipment: Brings LOTS of film. Film tends to be more expensive here than in North America.
Camping/Beach/Outdoor Gear: Bring TOWELS!!!! The Italians seem to use bed cloth-type pieces of fabric as their towels. If you like those big fuzzy towels, bring your own!
The weather is usually quite humid in the summer and a little bit more cold than rest of south Italy in the winter. You can easily survive with standard coats and light t-shirts ... and after all you can buy almost everything if you left something at home ;-)
Miscellaneous: Bring with you tons of money ;-)