Dear Shopping Savage...

Dear Shopping Savage,

I started dating a guy a few months ago and things are going really well. He wines and dines me and is a great conversationalist...but a horrible dresser. I want to drop a few hints in his direction, maybe even pick up a few things for him, but I don't want to scare him off or come across as controlling or materialistic. What's the best approach to handling this situation?

Signed,

Potential Boyfriend Fixer-Upper

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P.B.F-U,

You want to lead with a casual conversation. After strategically - and might I caution stealthily - looking through his closet, ask him when was the last time he went shopping. Don't make this a long discussion or it'll seem obvious what you're up to. Conclude by saying that the next time he does goes shopping you'd like to go with him. Allow a few days to pass and if he doesn't bring up shopping again, then you have license to be "creative". Tell him that your (brother, father, uncle, best gay male friend, whomever) has a birthday coming up soon and you want to start looking for gift ideas and want him to go with you just to get a "guys opinion".

Once you have him in the store he'll be like putty in your well-manicured hands. Start off by suggesting that he look around and see if he likes anything. If he doesn't bite then ask him to be a "model" for your gift and as he's trying things on, point out how great he looks in the new clothing. Have a sales associate - preferably another woman - restate your assessment. At this point, it should be easy to convince him to keep looking around/"modeling".

Pick out three head-to-toe looks for three separate occasions: work, weekends and weeknight dalliances. Let him have final say in how he mixes the looks per category, but be sure he buys at least two looks from each area. This works two ways: #1 - revamping a look from head-to-toe can get expensive so whether he pays, you pay or you divvy it up, he's going to wear the clothes because money was spent on them. #2 - if he really takes to the clothing (and the compliments that you may have to secretly solicit) then everything else in his closet will start to look out of place, which means you have successfully created a man that cares about his appearance, i.e. there will be more shopping trips for him in your future.

But let me end by saying that no one enjoys having their sense of style - or lack thereof - picked apart...especially when the advice wasn't solicited. You could be taking a gamble and the end result is not always predictable. Be sure that its worth the risk; you don't want the P.B. in your acronym to throw those last two letters back at you.

Need sartorial advice? Email me: ShoppingSavage@gmail.com