Perpetual Motion

An important part of a successful shopping trip is to keep moving.  If you're not seeing something that grabs you, keep going.  You will have your greatest successes and get your greatest finds if you cultivate a certain disregard for the act of shopping itself.  Ideally you shouldn't go looking for any one thing, just go with money and hope you come back with something good.  If you're looking for a nice pair of pants, you might overlook that perfect jacket.

Second Opinions

Having external input is invaluable when it comes to fashion and it helps you avoid things that you wouldn't normally see as the wearer.  But you have to be careful about who you're getting your advice from.  Not everyone is a reputable source.  Employees are sometimes untrustworthy, simply because they don't care.  And nor should they.  They're probably making minimum wage, or at best commission, in which case they're twice as compelled to get you into something expensive that you don't need.

The best idea is to bring someone with you.  Someone with decent fashion sense who has at least a small investment in the way you look.  A girlfriend or a close female friend would be best, or a fashionable male friend.  But remember, ultimately you're the one who has to wear it so don’t let someone else’s opinions override your own.

You’ve Gotta Work On It

Perhaps men aren't naturally inclined toward shopping, but we can be trained quite successfully.  The more you do it and the more you start to enjoy fashion, the less and less taxing a trip to the mall becomes.