Loyal readers (and really anyone who will tolerate my rants) know that a pet peeve of mine is when a grown man carries a backpack; That is, when he is not actually donning hiking gear and on a trail somewhere. Therefore I am often asked by male clients what type of bag they should carry. Typically I favor simple yet elegant choices, especially for my clients in finance, but for my creative set I like to think out of the box. This year I've found my solution in Prada's Hawaiian brief case (above). The classic shape/structure and sexy hardware demonstrate that you take your business seriously, but the print announces that you have plenty of imagination (and money). Note: I'd advise against pairing with the current Hawaiian shirt trend lest you be mistaken for this guy.