I will admit that most of my handbag opinions come from watching women on the sidewalk, and Rebecca Minkoff is a label that seems to have been built the same way. Rebecca moved to New York at 18 after finding design in her high school costume department, and in 2005 she and her brother Uri started the label. Her own history calls the mood bohemian femininity with a little rock and roll, which is exactly how I would describe the bags too.

The Morning After Bag, designed that first year, is still the one people bring up first. It gave a practical carryall a downtown point of view, and the label grew from there into clothing, shoes and accessories. The Megan, Darren and Edie families keep the everyday thread going, while fringe and metal bring in the after dark note.

Rebecca is still the creative lead today. I keep returning to the balance she strikes between a sensible shape and a little edge, and I trust a designer who started from what a woman actually needs to carry.

If I were choosing one place to begin, it would be the shoulder bag. The Megan Shoulder Bag and the Megan Small Shoulder Bag are the compact shapes I want on dinner nights, and the Mia Large Shoulder Bag leaves room for the long way home. The Darren Carrysome Bag, Darren Signature Carryall Bag and Signature Darren Carryall Bag are the roomier answer, the ones that swallow a laptop and a spare pair of shoes without complaint. Next to them, the Billie Fringe Hobo Bag and Industry Slouchy Hobo let texture do the talking instead of extra ornament.

In my fashion dreams, she takes an Edie Crossbody Bag through a day that ends at a crowded table, then tucks a Mab Studded Card Case into the Darren Signature Carryall Tote Bag for the commute. What I would skip: choosing a size by looks alone. Think about what you really carry first, especially when deciding between the small and large Megan or Mia.

What keeps me interested is the gap between why a handbag exists and how it changes an outfit. Rebecca Minkoff began with a bag meant to carry what a woman needed after a night out, and that useful instinct is still here, only with more shapes to play with. I would start with the size I need, then let the texture or hardware set the mood. That is a very New York way to get dressed, although I suspect I would still end up buying the second bag.