This is easier to do if you notice what your own brain is thinking when you look at an outfit for the first time.
An image like the one below contains a ton of information that a viewer processes almost instantaneously, and largely unconsciously. All of this information will register to the viewer's conscious mind as one, two, or perhaps three main emotions or ideas.
What I come up with isn't necessarily a single word; in this case, it's a single feeling or concept -- something like "polished/expensive/pulled-together."
That impression tells me that this outfit has a lot of Classic.
(If I challenge myself to identify which details are creating this response in my mind, I come up with these: the structured, expensive-looking bag; the gold jewelry; the neutral color scheme. But I'm not starting with the details and working outward to the Classic impression; I'm starting with the Classic impression, and only then figuring out which details are creating that impression.)
I then ask myself, Is Classic the only impression I'm getting? What else do I immediately notice?
Or, put another way: Is this a completely Classic outfit?
Baggy + elongated + oversized = Natural. So, this outfit has Natural and Classic.
I'll go back one more time and ask myself, Is this completely a Natural Classic outfit?
If I look at this outfit through the lens of Natural Classic -- "The Prep "-- there's one more element that stands out: sexiness.
Check out the cleavage, the high heel, the peep toe effect. Those aren't preppy; those are sexy.
So, I call this ensemble Romantic-Natural-Classic.. Also known as "Alluring L.L. Bean," or "Sexy Prep," or "Today's Southern Belle."
I'll double-check this determination by asking myself, "Is this outfit refined (Classic)? Is this outfit comfortable (Natural)? Is this outfit sexy (Romantic)?"
Yes, yes, yes.
I may take an extra moment to rule out the other four essences by asking myself, "Is this outfit otherworldly (Ethereal)? Is it innocent (Ingenue)? Is it avant-garde (Dramatic)? Is it playful (Gamine)?"
No, no, no, no.
* * *
I find selfies really helpful; for me, and perhaps for many of you, it's very difficult to see a mirror image objectively. If I'm not sure what impression my ensemble creates, I take a selfie, sit down, open the picture on my phone, and ask myself, "What's the first thing I think when I look at this woman?"
I'm an Ethereal Natural. Here I am in a top I recently bought and returned. I loved the top when I first saw it, and I wanted it to be right for me, but a little voice in my head told me something was off. I was only able to identify what was wrong after I took a selfie of the top and went through the mental exercise I describe above: "What's the first thing I notice?"
"Loose and comfortable" -- that's Natural. Check.
"Delicate and kind of Renaissance-y" -- that's Ethereal. Check
Oh, I see it: There is sweetness, a preciousness, a childlike quality. That is Ingenue. And Ingenue is what's not working for me.
(I do have a tiny bit of Ingenue: enough for a single delicate necklace, as you see here, but not enough for a strongly Ingenue top.)
Does an ensemble ever send more than three main messages? Occasionally, but it's very, very rare. The only time I ever encounter this is in some haute couture designs. Some designers are expert at sending multiple messages simultaneously in a single outfit. I can't remember encountering that effect in an outfit put together by a regular woman.
So, if you're not sure whether an ensemble is creating the effect you want to create, take a picture of yourself in it and ask yourself, "What's the first thing I think?"