I've had about four Russell and Bromley bags over the years but I don't know if that counts. I suppose the first "proper" designer handbag that I bought was a Mulberry Jayde in Kenya Darwin Oak a couple of years ago.
my first designer bag was given to me by my aunt; an LV monogram large noe
i think the first designer bag i actually bought for myself was a little black Gucci monogram pochette.
My first designer bag ever was a Bottega Veneta noce (walnut) Montaigne. I went straight from never having spent over $200 on a bag to doing that... I'm still not sure exactly what happened!