Friends, I have a wardrobe hole. I need to improve my bag collection.

Here is the thing. I have learned that in general, I carry 2 kinds of bag:

  1. The large tote or backpack which can fit my computer and heaven only knows what else in it. This is pretty much an every day need. I prefer smaller bags for appearance (esp. since I am not a huge person) but the reality is, most of the time I need to carry a lot of stuff around. (I do compromise in summer sometimes by using a shopper bag -- not as big as the tote but still relatively large.)
  2. A clutch or smaller "going out" bag, dressier than bag type 1.

So. For spring, I currently have a cobalt Ralph Lauren shopper, a navy Zara vegan backpack, a black-and-bone huge tote from Danier, and a hot pink clutch. I also have my grey Le Pliage which I have used all winter and which is boring the heck out of me.

What colour/ style bag would look good with my new leather jacket? (Blue) What type/ style of bag could I perhaps try to break myself out of the backpack/ tote trap? In spring/ summer I have less need to carry the computer every day, so can experiment a bit.

Also, what would be a good medium sized slightly dressier-feeling bag for going out in the evening. Sometimes a clutch isn't going to work and yet the totes/ backpacks just feel way too casual.

I'm a bag ignoramus, just like I am a jewellery ignoramus. Help!

Visuals/ Finds most welcome!!