Understand why he’s dressing that wayThe only way to educate him about style is to get to the root of it all. What inspired that look and how his clothes make him feel? This will help you when transitioning his look from bootleg jeans to straight cut jeans or skinnies, even replacing his favorite hoodie for a solid sweater.
Surprise him with clothing giftsTake a sneak peek of his wardrobe to get his size, then get home with a “hey babe, I found this on sale, and thought it would look great on you”. You bought the gift for him but in all honesty it’s for you. Bear in mind that you don’t want to change him into a completely new person, the idea is make him look his best self.
Compliment himYou got the gift then what? Encourage him to wear it and give compliments when he does, this way he will have the courage to let people see him in his new style.
Plan a shopping dateMen generally don’t like being told what to do, so approach this with caution. When you’re shopping, let him have a say and work around his opinions, of course guiding him at the same time. Help him pick out a few items that you think would look great on him, get him to fit them and do a mini fashion show for you, let him know amazing he looks and take pictures at the same.
Lead by exampleYour man will not be encouraged to dress well if you’re in sweat pants most of the time. Make the effort to dress well even when you’re just going out for coffee. Remember that you’re the one that initiated this change, therefore he needs to see it first from you before he call follow in your steps.
Get rid of the clothes you don’t likeOnce he has warmed up to his fashionably-enhanced self, get rid of those items of clothing that make you cringe. This can be done by donating to charity. Don’t do this all at once, take it one step at a time and most importantly ask for his permission. The last thing you want is to fight over his lost hoodie.