Hermès Birkin 35 in Gold Togo, because of the delicious smell(of the leather). But I would hate to wear the same bag everday.. I get sick of things pretty quickly.
Gucci Nice Microguccissima Top Handle bag - it is a lovely red colour, and very classy looking. It goes with everything I wear, and can survive all weather etc, so for those reasons, this would be the one I pick.
I would pick the Louis Vuitton Sofia Coppola because I love the style and functionality of the bag. It's a classic bag that would bring joy to carry every day.
Balenciaga City in black. It's my holy grail bag and I had been lusting over it for almost 10 years before finally getting it last January, so I don't think I will ever get tired of it.
Much as I hate to admit it, I could tunnel into my oxblood mulberry bayswater & nest. As a content, sleepy badger.
I used to worry about rain, when it was new. But, there are soooo many layers of collonil protectant on the leather, now, raindrops would need tiny hatchets to beat through.
It definitely wouldn't be appropriate in all situations. A bit on the edgy side to carry to the office. But if I could only keep one of my existing bags, it would be my Anna Sui for Coach Dragonfly Duffle.