QFW - 1 : Devil Wears Kolhapuri

Starting today, we present a 4-post series of posts on Fashion! Each post will have 5 questions like this one. Each question's points are given next to it. I'll maintain a scoreboard for this one. Get cracking guys!

PS: With Google's reverse image search all the more powerful than Tineye now, I hope you wont ruin the feeling and not reverse search these images. 

1.  See image. Which famous former first lady inspired these sunglasses? [ 10 Points]

2. Identify the shoe brand. The color says it all. [10 Points]

3.  He featured in Boom in 2003 and True West in 2002. He also played a cameo in Fashion. ID this gay fashion designer, who is based out of Colvale, Goa. [5 points]

4.  Connect these hitherto unknown geniuses. [15 points]

5. There is something bizarre in terms of clothing in this image. This clothing company uses this concept to sell its products and has turned into a $40 million company! Id this brand. [20 Points]