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Dear Arlington . I would like to help you with your question two . About boots with a suit. The short correct answer is that you cannot wear boots with a formal suits. The boots are too casual for the fine suit. Now however Bond and we fans like to breake the rules. The smooth calfskin of the Tetbury means that the faux pas is not a very grave one. It looks I'm fact quite elegant. I would also wear a boot like that with a suit but purists might find it too casual. Just don't go to far. Boots with a dinner jacket or white tails. The boots should allways fit the trousers You can use this guide for inspiration http://www.permanentstyle.co.uk/2008/08/a-sliding-scale-of-formality.ht… Since the boot is higher than the normal shoe the trousers should be fitted accordenly If you look at Bond in QOS you can see that his trousers are cut shorter to make the fit better . Wash the trousers first before the alterations Best regards Peter