Work shoe vs Play shoes with my new bag?

Which one, The Thigh-high low boot or the High-heeled Play shoes goes with my bag much better?
I`m having a time trying to see should I wait to wear the low boot or the high heel boot with the bag. Should this be an Everyday bag or a Special Ocassion bag? Its Leather and durable on a bus but the dirt it will accumulate daily... How do I clean leather?

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