Although I have my fair share of Tory Burch and Clare V totes and clutches, I generally only truly invest in handbags that will stand the test of time, those that I will continue to love after the season changes, trends cycle, and my tastes mature. This means I stick with timeless brands such as Chanel, Louis Vuitton, Gucci, Prada and YSL. My all-time favorite handbag is my Chanel 2.55 double flap. And while it was a big purchase when I got it 7 years ago (and would still be one today), its versatility means I use it over and over and over again bringing my per-wear cost into a reasonable range. My Louis Vuitton Speedy is a closet staple that can be dressed up or down, but the inability to put it over my shoulder has removed it from heavy rotation since having children. And I recently purchased a YSL nude clutch – another extremely versatile bag. This filled a hole in my closet and provided another option when I didn’t want to carry my Chanel purse. I feel instantly better when I carry one of my special bags.