The following represent a sample of some of the people who I think get it right when it comes to casual dressing. The styles are quite wide-ranging, from Sookie Stackhouse to Alexa Chung, but whether their style is more prim and proper or thrown-together cool, they all manage to wear clothes that suit their personality, look comfortable, but also look stylish.
Michelle Williams has such a fantastic mix of the classic and contemporary. She can wear something like a crisp shirt tucked into white capri-length jeans, but she also has a distinctly modern vibe. Maybe living in Brooklyn helps.
Natalie Portman has a wonderfully relaxed style of dressing, which always seems event appropriate and comfortable, but not sloppy.
Anna Paquin as Sookie Stackhouse has a charming retro style that manages to be both innocent and sexy.
And some other inspiring dressers…
I don’t normally like shorts that much, but with the cardigan and accessories, Rachel Bilson makes them look feminine and polished, while still casual.
Alexa Chung’s tom-boy style, dressed up with accessories and bed hair, makes her style feel youthful and fun. She never looks like she’s tried too hard.
Kirsten Dunst in a Boy by Band of Outsiders campaign. The colours and style and quite strong and almost masculine, but with the pencil skirt and heels, the look is all woman. You could wear all these pieces in such a variety of ways.