1. The
Gucci Hobo was a great price -- why not just keep that one. It's not flashy or anything, but it'll be useful as a trade-off everyday bag, and you'll have not spent a huge amount of money on it. I think it's a day bag, though -- not really a night bag.
2. The Gucci Boston bag combo. Again, this was a good deal. I think the colour *is* somewhat orange but not in a bad way, and I don't think that the design is tacky. I think the shape of the bag is nice -- useful and it is an added plus to have the wallet. The combo is more interesting than the black Gucci (no. 1), and I think could look really pretty on. I'd keep it, if I could.
3. Spy. It's too common, almost -- by now. I think I'd sell or return it. It does have an innate elegance, though.
4.
Prada. I love it, but I love structured bags. I think it does not necessarily have to be worn with dressier clothes, as you've worried. I wonder if the leather is easily scratchable, however? And the frame shape does limit its everyday use. I don't know if it actually would transition well into evening. It's actually really more of a day bag, to me. The leather is absolutely gorgeous, though, and I love the long shape of it (very cool this year, also) and the old Prada logo is so pretty. I am always torn on this, though -- it's the whole wearing a large logo thing. I don't like it, even though this logo is a pretty logo! If I'd gotten this bag for a good deal, though, I'd keep it.
3. Chanel. I'd buy a Chanel bag for my bag wardrobe, whether it ended up being the reissue or not. Very pretty. Not an everyday leather, though, in the case of the 2.55. This could be your evening bag.
4. Gaucho. It's got its charm -- the key is very appealing. But the western thing. I don't know. I guess I'd leave it, for the price. But the red colour is quite attractive, as an alternative to the white.
5. Muse. I like the Muse -- it would be a good everyday if you decide that you don't like the Gucci. The ostrich would be stunning -- but maybe too fragile for everyday.
6. Birkin. If you can afford it at all, this would be completely stunning and would last you forever. But this would still really be a day bag -- you'd not have a complete bag wardrobe with this one purchase. Also, in order to be practical you'd have to get an everyday leather one, not an exotic skin or anything more destructible and fussy.
