Do I need either of these?

One of the things I've always been addicted to is hand bags--of which I have many--but I haven't bought one for a year and the two I did buy are both summer bags. So should I give myself permission to buy this spiffy one from Tom Biln in Washington State at $50.00?

And if I do what colour would I buy. My two winter jackets are black with red trim and khaki with an orange inner shell.

Also I learned the hard way how wet this area is and while I have really good, heavy boots, all my shoes are made for city-streets and urban life.

And Back Country is offering this pair of shoes for a mere $85.00