To have a peaceful relationship, it's always better to reinforce the behavior you like rather than complaining about what you don't. Instead of telling your guy that his boots look like they survived the trenches in World War I, compliment him on on his spiffy new jacket. Even if he looks as though he just spent a two-month stint camping in the wilderness, you can find something to admire. For example, you might let him know that blue is a great color for him, even if he's wearing a wrinkled blue polo that he bought in the late 1980s. Simply knowing that you notice his wardrobe may prompt him to be more conscientious in his dress.
Help Him Out
Keep in mind that when it comes to footwear, your guy may have problems because he has likely been wearing sneakers since he was a toddler, says Glenn O'Brien, author of "How to Be a Man: A Guide to Style and Behavior for the Modern Gentleman." For this reason, he may need some guidance. Ask him to accompany you when you go shopping for a new winter coat, and encourage him to try on a few as well. This will be a prime opportunity to explain the difference between a Chesterfield and an Ulster, and why he should care.
If your guy didn't read the chapter titled "How Not to Look Stupid" in O'Brien's book -- which you conveniently left lying on the coffee table -- you may be left with no choice other than to be agonizingly direct. Gather your nerve and choose a relaxing moment to tell him his style may be holding him back. For example, you might say, "Bill, I love you, and it hurts me when people don't see your full potential because they can't get past the greasy fingerprints on your ball cap. Why don't we hit the outlet stores tomorrow and spruce up your wardrobe?"
Say It With Gifts
If all else fails, show your man what you'd like him to wear by giving him the clothes you like. Take a sneak peek in his closet to learn his measurements and bring home a snazzy new sweater that you "happened to find on sale" or a leather belt that doesn't look as though it could be in a museum of natural history. When he puts them on, let him know he is smoking hot -- in fact, he could be a clothing model because he fills out the clothes so well. When shopping, however, keep in mind that the clothing should enhance the person your man is, not render him unrecognizable, notes clinical psychologist Jennifer Baumgartner in the article "Stop Embarrassing Yourself!" for "Psychology Today." Remember what attracted you to him in the first place, and seek to play it up.