I think any bag in a classic black, luggage or dark dune.
For me its more about the color than the shape. I LOVE neutrals for the simple fact they go with just anything I decide to wear that day. I buy them and just *feel* like I will get so much more use out of them than I would a coral or purple bag. They are never limited to a season or specific outfit

Which in my eyes makes them classic.
But Im just like alot of the others, my taste changes too often to have one bag for 5-10 years. I'm not sure I could pick one bag that I have ever seen and honestly say I would carry it for that long.
My heart is pretty fickle when it comes to purses.
And I definitely do like the looks of the trendy colors... I've purchased (and sold) a few different ones. They are short lived with me because they sit on my shelf more than they get carried and that drives me nuts!
The bright colored accessories seem to work better for me. They are cheaper, you still get the pop of color each day, you don't have to worry about matching them with anything.
Also maybe you settle for a bag that is in your pre-set monetary limit instead of which bag you really had your heart set on. NOT to say having that limit is bad at all, because only spending what I deem appropriate on a bag is HUGE when I purchase also, spending too much makes me feel so different about the bag and I end up feeling guilty. But maybe that's why you might feel like you wasted money and are not happy with the purchases. You got a wonderful deal but you still do not have what you actually wanted or what you find useful.

I've been through this more times that I can count.
For me its all about finding the balance of what I'm okay spending and what I am going to be happy with and get the most use of. I am willing to spend a tad more for items (while still staying within my budget) I know I will use daily and only buy the colored most trendy items on clearance knowing I will use them a short time and then get rid of them. I, like everyone else, LOVE getting a deal but it doesn't end up being a good deal if I don't use the item.
