Bearing in mind there are brothers on the forum of all ages, backgrounds, countries of origin etc. I'm curious about when those first Ivy moments might have occurred...
For me, leaving aside any early suedehead affiliations, I'd say it was when I was 18, back in 1977, and getting fed up with listening to the punk stuff of the era. I'd started listening to people like Muddy Waters, Chuck Berry and Robert Johnson before then - mostly on my jazz-blues loving father's advice - so there was a leaning away from white music into black (I'd dipped my toe into the waters of Motown and Northern while still at school). We started going to see more movies: Brando, Dean etc. and somebody started handing round the Bosworth biography of Monty Clift. That's when I first saw those magical words 'Brooks Brothers'... Around the same time, I guess, I picked up my Dad's copy of 'Blue Note Album Covers' and began looking at the suits...
Around that same time, late 1970s, as a young teen I got some hand-me-downs from our neighbours' son: bottle green knit, tan 5 pocket cords, brown desert boots.
That was a defining moment. There was nothing subcultural about it, it just felt like I wore 'proper clothes' for the first time.
1961.
I was about 18 and a rather shy kid, not liking to be the centre of attention but wanting to somehow be different. I was a jazz enthusiast and got introduced to the style by a couple of guys I knew in NW London who were also keen on Clifford Brown etc. I`d been going through various looks culminating in Cecil Gee leather jacket, 501s (or plain Levis as they were then) and cuban heeled boots from Anello and Davide. However, finding the IL look was a kind of epiphany for me. Adopting it meant that I could be different without standing out, I could wear it for work and I could be completely comfortable, particularly in the summer when, in those days, it was impossible to get lightweight suits etc. I also liked the informality of the style, so at odds with both British tailoring and the Italian styles which were coming in and so, in a way subtly subversive.
As a result, I spent the 60s and much of the 70s in suits and ties and with short hair instead of Loons ,tie-dye and shoulder length locks.