The man to the second right is my great uncle Bernard - the one holding an old-fashioned megaphone. Our family photo album is full of photographs of him with his friends horsing around. He was evidently a popular and outgoing man in his youth. We estimate this picture was taken in the 1930s, before he joined the Air Force and fought in World War 2. He travelled widely and even on holiday his signature style was present: a striped polo shirt and blazer with pocket square, and baggy trousers tucked into socks. I especially love that Bernard and his friend are wearing mary-jane sandals since it is a typically feminine style, but looking at this photo I can imagine them coming back as a menswear trend. 
The photo I´m sending is a family photo from the 1960´s, back when my grandparents lived in Venezuela (Caracas) and runned a hotel called "Hotel Portugal" (so much for originality :P)The man on the further right corner is actually my late grandfather when he was about 30 years old! The other men are probably guests staying at his hotel, he loved to show them around town!
I find interesting their attire while riding their bikes and their overall look, which contains elements which are returning to mainstream fashion such as the pocket squares, hats and pins.
PS: I believe the 2nd man from the right is truly squint-eyed and not doing it for fun :
Recently i inherited around 50 albums full of photos from my grandparents, one of which had this photo.On the far right of this photo is my great grandad, Frederick A Rowley, and some of his friends.
I never knew him, but i think this photo just sums up the kind of man i picture him as.
Sadly i have no idea what time era this photo comes from, i would guess around 20's, as he married my great grandmother in 1919.
I don't know if he had a sense of style, but i think this picture just sums up the time, and the fashion.
I love this photo, and all the others i have of him.
He was a working man, but had such grace.
I'm very attached to my past, and i think this just shows why.
I hope you love it as much as i do.