To sharpen your typographic eye, first look at the big picture, the macro view.
What is your initial impression? Is it dynamic or quiet?
Does it engage you and how does it engage you?
Is there a focal point? Is there clear hierarchy of information?
You also have to look at the details, the micro view and ask yourself is the color of the type even?
What about alignment? Is there hanging punctuation?
Have proper smart quotes been used? Has the display type been kerned well?
I look at typography all of the time. it is the first thing I see when I look at anything
that has type, a sign, a menu, a package, a building, a T-shirt, a wine bottle, a cereal box, or a book cover.
I get a first impression.
I look at details, I deconstruct it, I think about the choices the designer made and the
possible reasons behind those choices. And of course I think about redesigning it.
That is what designers do, we can't help ourselves.
I want you to see typography everywhere like I do and to really think about what you are seeing.
That is the best way to educate your typographic eye.
Just keep looking, imagine what was in the designer's mind.
Think critically about the designer's choices and think about what you might do differently
to improve on it if you have the chance. Don't take anything for granted.
In everything you see someone made typographic choices, some good, some great, some bad.
The more you look, the more you will see and the more you will learn.
Believe it or not, you can learn just as much from bad examples as from good examples.
Collect good examples of type usage that you see, maybe even make a note of what you liked about it.
These can be springboards for your own design projects, inspiration is all around you.
I'm constantly amazed at the inventive uses of typography that I see every day.
The saying there is nothing new under the sun is true in a sense, but everything can
be reinvented and can be re-imagined with a twist or a new point of view.
And of course, there are so many new typefaces to try, more than you could ever use in a lifetime.
Keep educating your typographic eye, type is everywhere.
If you develop a habit of thinking about all of the type you see in your daily life, that's a great start.