While there are many types of envelopes, I am just going to focus on the most common choices for envelopes when you are purposely selecting/buying for an event. Otherwise, if this is just for general use, who cares what envelope you use. I always pick the cheapest or just send an email (normally the email because I can attach pictures of lolcats).
In the picture above there are four very different types of envelopes. Starting in the top, right corner and working clockwise, there is a standard postage size, announcement envelope, then a standard postage size, baronial envelope, then a non-standard size, square, announcement envelope (you will be paying extra to mail), and last is a totally non-standard envelope for a gift enclosure (mail at your own risk).
Announcement envelopes are also called A-line or square flaps. They are all this category because of their flap shape and the orientation of the flap along the length of the envelope. When you buy nice envelopes, this is where you have the most options. There is a little variation on how wide the flap is, but generally the flap comes down to almost half the width of the envelope.
I am very curious about why so many envelopes are square flap. Frankly, there are other 'fancy' flap shapes and the paper quality is what makes it a nice envelope. I do have a theory, though. If you think about it, there is less paper used to make an envelope with a flap like this than is used to make one with a big, triangular flap.
These triangular flaps are collectively called 'v' flaps. When it is a small 'v' that goes to the middle (or just shy of the middle) of the envelope, it is a baronial envelope (L). When the 'v' passes the middle of the envelope and almost goes the full width of the envelope, it is called a deep-'v' envelope (R).
Generally, the deep-'v's are considered much fancier than your standard baronial. On a practical note, you do have more room to write your return address on the flap of the deep-'v', but otherwise, it is just 'fancier' because it is more expensive... and it is more expensive because it uses more paper.
To be honest, you don't have many options when you go and buy envelopes. When papers for printing get made into their matching envelopes, there is only one style they get made into. Basically, if you want a deep-'v' envelope in a particular paper and there is only a pack of square flap envelopes on the shelf, you are out of luck.
While you can't pick and choose your flap style, you normally have a wide range of choices in envelope size. Most rectangular envelopes that you see for sale are going to be standard postage (provided they aren't too big/too small or too heavy when it gets filled). The main, non-standard postage, envelope option is the square envelope. The reason the square is extra to mail has to do with what the post office does with its envelopes. When the mail comes in, there is an automated process for the stamping and initial processing. A rectangular envelope has a clear orientation on it's top/bottom and sides whereas a square does not. So the machines cannot process the envelope properly and it needs to be hand-cancelled. Hence, extra postage.
If you put this in the mailbox, it will get delivered but your recipient will be paying the extra postage. Same thing if you put something too big in the mailbox. If you put something too small in (like that gift enclosure from the top of the post), you might not be so lucky. It might not even make it to the recipient. Small things get mashed up and lost. Of course, you can put anything in the mailbox and provided there is enough postage on it, it will be mailed. I have put things smaller than the 3.5x5 in. size requirement in the mail and it worked out just fine.... but it is smaller than what the post office says that you can send. So decide if you feel lucky.
Hope this is a good start to some of the options. There is much more to be said on sizing, materials, and shapes, but let's just leave that riveting page-turner for another day.
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