Someone asked me this question today. That's what I get for trying to help someone out with their wardobe. Anyway yes personally thinking about what should I wear or if I am giving advice to another what should they wear I tend to think of certain aspects of fashion that's a stylish inspiration for me.
It can come from anywhere such as street style on various blogs i.e The Satorialist, Altamira NYC, garance dore

Personal blogs are comforting because you see fashion enthusiasts take pictures of themselves revealing their outfits to the world.

Movies is another great inspiration for me. No matter how time passes movies can come and go however some movies are truly timeless.

Sometimes emerging from those movies come style icons, actresses that exudes grace, a personality to match and fabulous clothes.

So, what inspires you?