Most Helpful Guy
I first look at her face. Does she smile? Does she appear to be happy?
Is her face overly made-up? I don't care for girls who wear a TON of makeup; some is fine, but I don't like the Barbie or Beauty Pagent look.
I will look at her hair; I like longer hair, but at least I want to make sure she doesn't have that short, old-lady, "I've given up" haircut.
Then will look at her clothes and her body. Does she have some style? Is she comfortable? I appreciate a bit of style, but I don't want someone who is totally style over substance. If we're going to be walking all day, don't wear 5" high heels that kill your feet; that kind of thing. Simple is best.
I really don't care about shoe styles or accessories or any of that; that stuff is mostly "lost in the noise." I will notice her overall body shape, and her clothes in a basic sense, but mostly I'll notice if something is BAD, as in, ill-fitting or totally inappropriate for the situation. If I don't really notice anything, then chances are everything is fine.
Really, 90% of my attention is going to be focused on her personality and attitude, and most of the remaining 10% will be looking at her appearance to see what it says ABOUT her personality and attitude.
On one hand, I (and most men) appreciate all the work girls do to look good for us, but often it's overdone, and sometimes WAY overdone, when most guys would prefer a simpler look. We aren't talking about special events, when it's natural to "dress up" some, we're talking day-to-day.
To me, a girl in a simple cotton sun dress is hotter than any cocktail dress or evening gown.