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The type of suit a man wears will tell alot about his style and personality. Wearing a Pen Strip Suit. Pinstripe suits are a classic look and can be worn for multiple occasions such as work, or evening out. You will see many pinstripe suits in the financial district of New York City whose professions include bankers and stockbrokers. Dressing up your outfit with Cole Haan shoes can make that perfect statement that you are moving up in the world.