As a menswear personal stylist, I have so much fun helping men identifying and transforming their style, but when my boyfriend showed up to one of our first dates in sweat shorts and thought they were totally acceptable, I knew I’d have some fashion struggles ahead. Three years later, my boyfriend’s wardrobe has made drastic improvements and I realize I am not alone in this situation. It’s not that you love your boyfriend any less because of how he dresses, or that he’s less of a person in your eyes, but sometimes guys just need a little help to reach their full fashion potential.
1. Get to know why they dress the way they do
Unless your boyfriend has a very particular style, chances are, he just doesn’t care or know any better. My boyfriend dresses for comfort and many guys are like this. What you need to do is show him how he can be comfortable in more stylish clothing that actually fits properly. Try and understand their point of view. My boyfriend is large and in charge with very athletic legs, so he doesn’t feel comfortable wearing slim-fitting jeans, but that doesn’t mean he has to wear baggy jeans. You settle on a happy medium straight leg pair that has lycra in it which means it stretches and will be comfortable and flexible as he moves.
2. Surprise him with clothing you like
You know, those gifts that are for him, but are really for you. Tell him how you saw it, loved it and thought it would look great. Ask him to try it on! I’ve learned through my many years on the retail floor, once the man gets in the fitting room, you’re halfway through the battle.
3. Offer words of encouragement
When your guy finally makes the move and wears something you picked out you need to encourage, encourage and encourage! “Oh my goodness, I can’t believe how handsome you look! You look so hot, babe! Seriously, those jeans are so flattering!” Done.
4. Invite him somewhere he’ll have to dress up
If you want to elevate the wardrobe of a perennially casual man, you need to give him a reason why he needs to elevate his look. You need to invite or bring him somewhere where he has to dress up. Then, when he’s sporting his new look, you compliment, compliment, compliment. When my boyfriend and I were celebrating our first Christmas together, he was invited to my family’s house. I informed him weeks in advance that everyone dresses up, and he showed up in a 3-piece suit. He was the most dressed up person in my house, but he looked good and everyone let him know! If he could wear a 3-piece suit for Christmas, he can wear a button-down shirt on our next dinner date.
5. Slowly get rid of the clothes you don’t like
If you think you’re just going to wean his favorite jeans from his hands, it’ll only be when they’re cold and dead. You have to slowly rotate new clothing in before you can sneak the old stuff out. Spring-cleaning has never felt better! Help your boyfriend go through his wardrobe and donate clothing that no longer fits him and try to replace items you think he could do better with before you cause too much trauma to his sartorial psyche, but before you know it, it’s out with the old and in with the new! 
