I didn't ramp up at all.
Throughout my 20's & most of my 30's, I would own one Fossil, use it every day for every occasion until it wore out, then I would buy another Fossil. I had one that the zipper broke on, and a co-worker brought me into a Coach boutique near our office. I think that was 2006, at age 36, I said these words "OMG, I would NEVER pay $300 for a purse!!!!"
In early 2007, the Ugly Betty episode "Swag" aired in which Betty got a (85th Anniversary) Gucci when they were purging the closet at the magazine. I fell IN LOVE with that Gucci. I searched for it online... which is how I found TPF!!! And I found that it was currently available on Neiman Marcus. At that point in my life, I was 37, in my career for 15 years, owned a house and had a level of savings I was comfortable with. This also exactly coincided with my bonus timing. Despite the fact they said it was a $4,500 bag in the episode, it was actually about $1,900 with tax. - I gave it some consideration, and decided to get the bag.
That was my "gateway drug". I had loved LV monogram since high school in the 80's, but of course couldn't afford one in high school. And once I was starting my career in my 20's, I wasn't about to spend that amount of money on a bag. Money was for rent & bills, saving up a down payment for a house, and travel. - But once I got that Gucci, I thought... well why not get an LV which I've always wanted. So I did. This one was about $1,400.
However, neither of those bags was good for everyday use going to the office (they were both shoulder bags... which I couldn't carry with my laptop backpack, and the Gucci is velvet!!)... so at that point I started buying Coach (which are in the $300-$500 range)... and then I got a 2nd LV that was more practical to carry to the office (that one was about $800). And then I got heavily into the 2006-2008 Tokidoki for LeSportsac bags.
So I went from $100-$120 Fossils, straight to an $1,900 Gucci... and then all over the place. Just whatever I happen to like. My per bag comfort level caps at around $2k. I've paid slightly more for a few: my Chloe's were right at that point, and slightly over with tax, and a pre-owned
Prada Fairy that I just recently got from
Fashionphile.
I've been known to buy a few $1k-$2k a year, and/or many Coach bags per year... which have added up to double-digit thousands in a year. But I don't think I would ever spend much more than $2k per bag in today's dollars.