I posted this about 5 years ago in a similar thread. Here's my long story of the first designer handbag I ever purchased.
In the fall of 2000 my best friend had purchased the Kate Spade "Sam" bag in black nylon. At the time, I thought she was crazy for spending that much money on a bag. However, she was working, while I was a broke student starting my last year of law school.
Fast forward to March 2002. I was in middle of my articling year and had never been so stressed in my life. I lost a Motion in Court, tripped and fell on my way back to office (in the pouring rain) and was fighting the tears when I got back to the office. I just sort of snapped. I called my friend who happened to work near to Holt Renfrew, told her that I was about to do something drastic and asked her to meet me at Holts on her lunch hour.
We met up there and I bought the first Kate Spade bag to catch my eye. It was a black and white stripped canvas tote with a bright crimson red lining. I think it was the Monaco stripe pattern. I swear to you all, that day money did buy happiness.
The SA was so nice to me. I may have told her it was my first "real grown-up lady purse", so she wrapped it up in one of the pretty Holt Renfrew boxes and even tied it up with ribbon for me.
I returned to the office. At the time, all the articling students shared one big space, with each of us having our own cubicle. Of all the students, I was the only female. So I strutted in to the office, announced that I had spent the last 7 months listening to their guy talk and they owned me 5 minutes of girl-bonding. I proudly displayed my beautiful new bag to them. To their credit, they played along, offered several compliments and told me I deserved it.
It was the uniqueness of that particular bag, the quality of the construction, the feeling of luxury and the idea that I could reward myself, that "flipped the switch". I began to take an interest in fashion and worked on developing my own style.
That bag would be the gateway to many other "because I deserve it" bag purchases over the years. I've refined my tastes and edited the collection quite a bit in the 17 years since that fateful day, flittering between contemporary and luxury designer handbags. Although I retired that first Kate Spade bag many years ago, I held on to it until just last year, sending her off (with a Marie Kondo, "thank-you for your service") to a consignment shop. I think she still resides there waiting for a new owner.
It was a google search I did in 2012 trying to find the name of that first bag that lead me to TPF. I've mostly lurked here ever since.