I make a lot of simple single executable applications for various things at home and at work. Icons always seem to be a problem for me I am not a designer. Like most I can do a little here and there with photoshop, gimp and paint.net. However I should not be trusted if things need to look “good”.
The question is how do you deal with icons for small (often one day) projects that just need something unique. Nothing flashy just enough that the user can associate it with its use and find it quickly on a desktop. Even something like the Gravatar fractal based icons would be a good starting point.
I’m aware that when asked about free icons the big box of knowledge comes back with many results but I want to know what my peer (and superior) developers do in these kinds of situations.
If it’s icon-making software you use and you’re enough of a designer that it doesn’t look awful that’s great, but may not be doable for me.
Do you ever buy icons? What is a reputable site for commercial products and where would you steer clear of?
Lastly what types of licenses do you look out for when using free icons found around the net?
First off, a disclaimer – I’m not an application developer, but a (amateur, technically speaking, since I’m not getting paid for this) web designer/developer. I use a lot of icons in my projects, but since I’m on a budget of $0.00, I have a fairly large collection of icons obtained from the internet, so I feel that I should have some say on this matter.
Automatically Generating your Icons
Automatically generated icons are a big no-no for me. Unless your application is a fractal generator, the generated icons usually won’t fit the application. You’re better off sticking to the plain
or 
if you’re using this.
Free Icons
Free icons are pretty good if you don’t need anything too fancy. You didn’t mention anything about whether the projects are commercial in nature, because legality is a big factor in determining what you can use. Also remember that in Vista/Windows 7 icons can go as big as 256×256 – icons of that size are not usually available for free icons.
In terms of legality, options for using free icons for commercial software is a lot less, than say, a freeware/FOSS project. Look carefully at the licenses: Creative Commons
is a fairly popular choice these days, but there are others. Usually attribution is required, which usually means acknowledging them in the “About” section or the “README” file.
Sources for Free Icons
Like I said, I know of a lot, but these are the ones that I feel you should look at first.
Designing your own
Well, I can’t say how good the icons are without actually looking at your icons, but there are certain things to keep in mind, specifically the Windows Icon Design Guideline published by Microsoft.
There are far too many if you want a complete list, but these are the good ones