As both an avid reader and someone with a passing interest in style and fashion, I think that Textbook is a pretty awesome site. It’s a blog that takes fictional literary characters and imagines how they would dress today.
Some of my favorites:
Jay Gatsby -- F. Scott Fitzgerald’s The Great Gatsby
Count Dracula -- Bram Stoker’s Dracula
Elizabeth Bennett -- Jane Austen’s Pride and Prejudice
A few other great posts:
Aphrodite -- Greek Goddess of Love
Daenerys Targaryen -- George R.R. Martin’s A Song of Ice and Fire
Dorian Gray -- Oscar Wilde’s The Picture of Dorian Gray
Edmond Dantes -- Alexandre Dumas’ The Count of Monte Cristo
Howard Roark -- Ayn Rand’s The Fountainhead
Hurricane Irene
Lucrezia Borgia -- Daughter of Rodrigo Borgia, Pope Alexander VI (Wikipedia Link)
Pokémon
