Fashion is a timeless and cyclical form of art. Anyone can match and look decent, but you have to have a certain eye to have real style. Everyone has to wear clothes, so you might as well be stylish while doing it, right? Well these documentaries will show you that many others think so as well.

Bill Cunningham: New York

Bill is a street photographer, best known for his work in The New York Times Magazine. He had a modest up bringing; with his love of fashion starting as a young child when he noticed the hats women wore to church. Bill is highly respected in the fashion industry for having a great eye and knowing what is “in” at that particular time. In the documentary he says, “Fashion is the armor to face the reality of everyday life.” He cares for the clothes, the color, the cut— not the fame or lack of, of the person wearing it. Bill merely wants to document the evolution of everyday style, whether in the street or charity galas.


Fashion legend, Iris Apfel, is known for her tremendous collection of clothes (she has apartments dedicated to just clothing) and note-worthy style. She says she has “no rules” for her style, and what she wears. Iris is a fashion innovator, not scared to do different things and stand out. The documentary tells of how she has been collecting and haggling with sellers since she was young.

Iris is a businesswoman, interior designer, and most importantly a fashion icon, always wearing her trademark big round sunglasses. This documentary takes you through the extraordinary life of a true maverick.

Advanced Style

Ari Cohen Seth created this documentary, influenced from his blog Advanced Style, showing the glamorous fashion and style of women over 50 years old. This documentary proves that with age, things can get better. Following the lives of seven stylish women, you see how nothing deters the women from getting up everyday and indulging in their true passion: fashion. Proving that glamour and old age aren’t mutually exclusive, these women take to the street to showcase their unique style.

If you like fashion or true style you will love and respect these documentaries. Fashion can mean anything, as long as you believe in yourself and take risks. And don’t worry, fashion is ever evolving, so if that hat you love so much isn’t cool right now, if you keep it around, it might just be cool again in a few years.