We know you love your man, and like to see him at his best. Whether you are strolling downtown or dining out, there is no reason to not look good. However, you regularly see couples where one dresses stylishly, while the other dresses like they are going to be doing yard work.
Why does he dress that way? Maybe he has a peculiar style, but more likely he just does not know any better. He may say he dresses for comfort, but more likely dressing nicely is outside of his comfort zone. He is not willing to take a chance and, thus, dresses in what he is "comfortable" with.
Show him that he can be just as comfortable in quality clothing that fits well. Looking like a slob is born of the fear of being different, or fear of making a fashion mistake. Most people can't pull off a look from a fashion magazine. He needs to find a look that is him.
Praise his efforts. Telling him what to wear will not work. He wants to look good for you. Build his confidence. Baby steps and praise, like training a new puppy. When he makes an effort, you need to give him a "Wow you look really hot!" Tell him what you like and he will try to please you.
Don't act like his mother. He does not want to hear, "You need to get some better clothes," but would love to hear, "Your butt would look great in those jeans." This may particularly work well if another guy is wearing the jeans you're admiring.
Get him into a dressing room. Many guys say they don't like to shop, but once they are trying stuff on and having fun, they love it. Does he have a friend who dresses well? Recruit him into your endeavor.
Just be sure to only give him things to try on that could actually work. If he is a large, and there is only a medium left in the store, do not ask him to try it on just to see how it looks. It will either not fit or look great and not be available. Either way, he is frustrated.
Plan events where you dress up. Prescott is not lacking for nice restaurants, plays, gallery openings, etc. Give him a reason to dress nicely and then compliment him. Once he is out in his new clothes, he will start getting compliments from others. This will do wonders for his confidence and encourage more stylish choices.
Purge. Do not throw out his favorite shirt, he will resent you for it. Clean out your own closet, and when you have the pile all ready to take over to Stepping Stones, ask him if he wants to add to it. Offer to help as he tries on everything in his closet and see what doesn't make him look as good as he could.
Once there is some empty room in his closet, he'll want to fill it and you'll be ready to take him shopping.
Ray Sola can be found at Man At Leisure in the Bashford Courts Atrium Mall,
130 W. Gurley St., 2nd Floor. Call 928-776-4874.