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Shoes make the man, it is a fact. You can dress semi-decent, but the shoes will take it over the top... its a very important accessory that is neglected by the average man.

The key to shoe shopping is leather soles, 90% of the time they will be made in Italy (because the best shoes are always made in Italy). Your signature shoe should never have rubber soles, nor should it be too "clunky"... streamline is the key. Personally I prefer ankle high boots, but they may be a bit too expensive for your budget.

The trick to leather soles is that even though you are buying them for the leather on the bottom, you will never actually wear them that way. Take the to a great shoe repairman to have no slip rubber bottoms installed, your shoes will last for ages with this little bit of extra care.

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This is a good tip. Leather soles can wear out very, very quickly. This kind of shoe is not your walking around, doing errands shoe. I've worn out very nice soles this way, which was pretty dumb.

By the way, use either shoe trees, which some advise against because they say they will stretch the shoe out too much, or stuff your good shoes tightly with crumpled up newspapers when you're not wearing them. Every time, right away. Otherwise they will very quickly settle into deep wrinkles that will ruin their look. Think of it as preserving your investment. And good leather shoes can be quite an investment.