Reddit mentions of adidas Originals Men's Stan Smith Leather Sneaker, Core White/Core White/Dark Blue, 4

Pants stick out the most to me.

IMO black jeans are some of the most versatile pants you can get.

I'd get a pair of those. I personally love these, but if that's too skinny/too much, I've heard great things about Levi's 511.

Next, like a lot of other people have said, a minimal white sneaker is king. For your price point, look in to Van's Sk8 Hi for a really casual/skater look, Stan Smith's in White/Blue for a more simple look (reading back over this, I realized you were in Italy - Stan Smiths are so fucking popular it's ridiculous. As are the Adidas Gazelles. Not bad options if you want to fit in, but keep in mind you'll be wearing what everyone else is wearing). Honorable mentions are the Converse Chuck Taylor II Highs and Lows. These might be hard to find on amazon.it but make sure you're getting the Converse Chuck Taylor II - they updated the sole and it's one of the most comfortable sneakers you can get. Durable and iconic as well.

You said you're in Italy, so I reckon you're not -too- worried about heavy outerwear.

Honestly, I'd skimp on the watch if I were you - it's an accessory and IMO not nearly as important as the other staples. If you do get a watch, Timex watches are fairly popular among MFA users and pretty cheap on amazon.

Polo 3 isn't actually that large. Nor is 5. Orange is a hard color to pull off though, so I'd personally avoid wearing that.

Lots of Americans dislike polos but I spent this summer in Italy and polos were super popular so just keep doing that I guess.

I will say, all of your shirts are wrinkled. Like straight up all of them. After taking your clothes out of the dryer, hang them up. Maybe buy some hangers if you don't currently own any. Hanging them up cuts the wrinkles down so much.

If the product is available in Italy, these Gildan shirts are great quality for the money. They're not amazing but you get a lot of options. There are several options there for different packages, but I'd stick to toned down options. When most people start caring about how they dress, they don't really know how to incorporate/coordinate color properly. Low-saturation is easy to coordinate. Black/blue/greys/whites/earthtones. For example, there's a deal going on for people in the U.S. right now to mix and match tops. You can see it here. I think these outfits are done really well overall, but as you can see the colors are really muted.

A large part of looking good is in the hair - your hair in the last 2 pictures looks super good. If you need product to do that, I'd use part of the $500 to get that. Keep that shit up.

Also look into cologne - Amazon is a pretty decent place to get them. I personally love Bvlgari Man Extreme and I get it through Amazon. Consider stopping by a Sephora or something and testing out colognes to find one you like - you can typically find it on Amazon for about $60 for 3 Oz.

I'd also stay away from V-necks as much as possible. Might just be me, but I really hate them.

I'd also consider no-show socks. I realize you're in Milan, so if you want to go all in on the Milan look, I'd suggest the following:

Simple, well-fitting shirts.
Black skinny jeans, pinrolled.
White sneakers - Stan Smiths and Superstars are ubiquitous in Milan.
No-show socks.

Your one suit is great. Make sure you have a dress belt that matches the shoes you wear with your suit. A suit without a belt is hard to pull off.

When shopping on amazon - be sure to avoid shit like this. Cheap, chinese made, won't look anything like the product pictures. This sums it up pretty well. Buy stuff from brands you've heard of - you've heard of them for a reason. That being said, only buy shoes from shoe companies and clothes from clothes companies. Tommy Hillfiger and Calvin Klein and the like make decent clothes but terrible, terrible shoes.

I looked through jackets on amazon.it and this was the best I could come up with - not cheap by any means, but it'll be good quality and bombers are super ubiquitous, esp in Milan. Unfortunately, it's still about $90 but jackets get expensive quickly. It would be smart to get a simple sweatshirt or hoodie. This can be layered under the bomber for a cold night. I'd stray away from a zip up hoodie, as your bomber already has the edit zipper***.

I also just remembered that Cheap Monday is super popular in Europe - This is a great option. Low vans are also good shoes to consider.

That's uhhh... all that comes to mind. It's super disorganized and I threw a lot at ya so have fun with that. Super jealous that you get to go to school in Milan. Have tons of fun dude.