I much prefer the second bag. So this would be my reasoning ( and please understand I am no mathematician - this will be obvious. 😂)
When I went on the website there is 10% off first full price order so the 2nd bag would be approx £410 rather than £455 .
If you bought the first one which frankly I wouldn't use if someone gave it to me (but that is a personal choice ) you are still paying the thick end of £300.
So if you have the budget to pay £400 rather than £300 for a bag I would buy the 2nd one for the 10% off. If it goes into the sale they may take 25% off but not guaranteed. Or just wait and see if bag 2 goes into the sale.
But if I bought bag 1 - which I wouldn't - I think sometimes things go into the sale for a reason - I don't think its nearly as nice or elegant as bag 2 & would you kick yourself if you bought a bag you didn't love for £300 you could have put towards a bag you really did like ?
I hope that rather muddled thinking comes across and of course the extra £100 may not be possible but that's the way I would look at it.
Oh & don't think bag 1 is a classic, it looks a bit "fashionable" to me even if from the archives BUT I am not a bag expert - just personal opinion. & if it is tweed will it last as well as bag 2 ?
Well my thoughts if it helps at all - I suspect not 😊But enjoy your choice - whichever it may be