Newbie here - Which Coach should be my first?

Definately the pebbled leather that Vanilla posted. That shoulderbag is so extreamly comfortable. I would get a Leather bag with a Signature Mini Skinny for credit cards.

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That comes in Black too. I seriously want the Black.

If you prefer signature they do have the same style in signature. I personally think the Pebbled leather is the way to go though, so buttery soft and keep getting better with time.