I wear my bags for about two or three weeks straight and then I want a change, so I switch my bags out. I never give it another thought to what I am wearing that day, for everyday. If I am dressed up, I switch my bag for that event. But, I am pretty casual on most days. I work in a very causal job (high heels are a no no here). I have three kids so I wear what is comfy and enables me to chase my kids too! Most of the time, it is jeans....sometimes something more sporty. Sometimes, I dress the jeans up some. But overall, casual. I love all my bags, and just want to wear them and love them. So here's the question: do you always match your outfit to your bag? Are there certain bags that are dressy/casual??? I have a Baggy GM, a mono speedy 30, a mono stephen and a embossed polly. And I wear them anytime I want!!!