Overhaul His Look
Unlike women, most men will not jump at the chance to be "made over." Still, men are just as likely to need a makeover -- sometimes more than their female counterparts. Getting the job done will surely take some convincing but, as you develop your plan of attack, keep in mind that the result will be worth the work.
Love on him
The more you show affection, the more likely he will be to listen to your ideas. Be sure to talk up his positive characteristics just as much as the makeover-worthy weaknesses. Then, suggest he move on from the commemorative fraternity t-shirts he wore in college so that his wardrobe reflects the successful man you've grown to love.
Pay attention when you and your man are out to dinner or just walking through the park. If you see a style you like, mention it casually. Point out that the guy at the bar is wearing a tailored blazer that would look great on him. Offer to take him shopping the next day.
Ask his opinion
As you casually flip through a magazine, ask him what he thinks about a particular outfit, haircut or manly accessory (man bag, anyone?). Throw in a "this would look so much better on you" comment to get him thinking about trying something new.
Surprise him with a gift
Sometimes, it takes a little more than prodding to get men to see the light. The next time you visit your favorite discount store, stroll through the men's department and bring home one or two new pieces. Your thoughtful suggestions could be the launching point for a full-on makeover.
Offer to do the dirty work
Even if your guy is sporting the world's worst uni-brow, he probably will resist a trip to the salon for a much-needed wax. The next time you pluck, make sure he sees that it takes effort to achieve perfectly arched brows. Then, offer to do "just a little plucking" for him to see what he thinks. With luck, he'll be in inspired to keep it up, and maybe even take the makeover to the next level.
Make an effort to rid your wardrobe of frumpy standbys, and make sure he sees you doing it. Let him know that you feel the need for a change and you'd like him to join you in editing the closets. When it's not all about him, a joint update may sound pretty appealing.
Give him an incentive
Plan a romantic weekend or dinner and make it clear you'd like to celebrate his new look. Set a realistic date, perhaps a month away, and casually remind him how excited you are for the big event. With a goal in mind, you will both have something to look forward to, and he'll be motivated by your gesture.
Make it fun
Team up with another girlfriend whose man is equally in need of a makeover. The entire experience will be easier for him to digest if he knows his friend is going through the same thing.
Give him a dose of reality
Some guys honestly do not know how far they've fallen. Guide him through an honest look at his wardrobe, grooming habits and daily routine. If he really is in need of a makeover, the chaotic closet, exposed nose hairs and rumpled shirts will convince him to participate.
Call in the professionals
If all else fails, buy a gift certificate for an hour-long session with an image consultant. He may not seek professional help on his own, but seeing that you pre-paid for a session may be all the convincing he needs.