Not sure if this counts, but my first expensive bag was an Herve Chapelier I got in 8th grade (I'm now 20). This March I bought myself a small Coach dusted suede hobo... to quickly be followed by a Coach Hampton's tote and an Andrea Brueckner saddle bag (best bag EVER). Still getting used to spending over $100 on a bag, hopefully someday I'll get up the guts to buy a Chloe Silverado or Paddington.