on the hunt: cross body bag

Zara // Kate Spade Saturday // Mango

Madewell // Kate Spade Saturday // Kate Spade Saturday

Mango // Kate Spade Saturday // ModCloth

I've certainly refined my thoughts on handbags over the years. In high school, I had many different styles and colors (nothing fancy, of course) that got swapped out according to shoes and outfits. Be caught with brown shoes and a black purse? Absolutely not! (So serious in those days.) 

In college, I kind of lost fervor for the cause when I was focused more on schlepping drawings and models and chipboard around campus. No one in studio noticed if my purse matched my shoes. I tried to keep a few "going out" things meant to hold lipstick instead of history books but they rarely got used. 

Since I've moved to NYC, the city of designer purses and "it" bags, I've completely fallen off the radar. I have one purse at a time (typically no more than $100) that I use until it falls to pieces. Only one option means one less decision when getting ready in the morning. Only having one bag means I also have to looooove it, so I've really distilled what I look for in a purse to meet all my neuroses:

cross body--for hands free metro card wielding and subway bar grasping

smaller strap--for over the shoulder/crook of elbow holding at parties

colored leather (or faux leather)--for not offending either side in the ongoing black vs brown debate (but I also feel a rich caramel brown can reach across the aisle sometimes)

So I'm the hunt for a new, perfect bag for our trip to Italy. I'm looking for something on the smaller side--enough for my wallet, phone, bottle of water--so I don't kill my shoulder while out being a tourist all day. I want it to be accessible for quick gelato transactions but also secure enough to ward off pick pockets.

Any suggestions that meet my wildly specific list of requirements? Which one do you like above? I like them all, I'm not sure I can decide!!