How to Make the Perfect Outline?

Funny I do the same thing. Must be the right/left brain type of thing. I use a round/square cutter to trace then pipe.. but there are times I don't outline. I think it's whatever you are comfortable with.

I usually have to rotate my cookies in order to get an even outline. If I don't, my hand eventually gets in my line of sight and I can't see how the icing is dropping onto the cookie.

I don't always outline either - in fact, I often don't outline on rounded shapes where I know I want to do a big-ish border. It's faster not to outline, and often I can get a more uniformly rounded edge when I don't outline. I call the method I use (for flooding w/o outlining) top-coating, and I describe how I do it in detail in both of my books and also in my latest video series, which you can find on my personal website.

If I have circle or square cookies to do, prior to baking the cookies, I get another circle/square cookie a fraction smaller than the cookie I was cutting with and make a light indentation with the smaller cookie cutter...that ensures, most of the time, that I will have a nice, perfect circle.

I have not had the guts to do designs without outlining, so I am no help there.

I also started filling my cookies without outlining first.  I had tried it several times early on - but couldn't get the icing the right consistency.  But once I practiced enough, I got it.  It's much easier, and as Julia said - trying to outline there is always a blind spot and even when I know it's coming - it's hard to adjust for it.  I either end up too high or fall off the edge!  But if you rather outline - when you cut your cookies you can always make an imprint in the dough before you bake and then you have a 'built-in' outline to follow

Yes I find if I want the outline to be as consistent as possible I need to trace a line. I also turn my cookie and don't outline in one motion. I have just started trying to use the 20 second icing sugar belle talks about. I almost always outline then flood!