I wear my hair and makeup like this pretty much everyday. I'm actually shocked I could find a picture almost exactly like my hair. lol
I've always thought my hair looked nice, but a week ago a woman came into my work and said my hair looked way too formal. Her face implied she thought it wasn't a good look. It was weird, but it made me paranoid.
If you wore your hair like that while doing oil changes on cars or working as a painter, maybe it would be too formal. I can't think of any situation outside of fairly dirty jobs where it would be inappropriate.