How many pairs of basketball shorts and ratty T-Shirts can you handle before going insane? What is it about the twenty-something guy that makes him struggle with putting together a grown up outfit sometimes?
Every time I go into J Crew and see the mannequins I can’t resist pulling the tags to check the prices and wondering to myself if my boyfriend would mind if these clothes magically appeared in the closet for him (he’d probably love it). But how much does that overstep? I certainly would HATE if he all of sudden was like, “hey babe, your clothes are terrible, why don’t you buy some stuff I like a little bit better.” Clearly that is not the solution.
So, how do you dress your boyfriend, without him knowing?
First step: get him to the mall with you. For some women this is the largest challenge they will ever face. It’s a well-known fact that guys shop so much differently than us. I’m used to making the mall a whole day, floating through stores, touching everything that looks cute, trying on a bunch of stuff, getting a whipped cream caramel cooler, lingering outside store windows and hunting around the sale racks for potential finds. Guys go to the mall when they need to buy one thing, walk into a store, find that one thing, then buy it and leave the store and/or the whole mall. For them it’s about utility, for us it’s a fun afternoon and our favorite form of cardio. Basically if you can get him in the mall you’re already most of the way there.
Second Step: Encourage him to try things on! Mention how great it is that the mannequins make it so easy to put an outfit together and choose one that you like to use as an example. Naturally the clothes should be right beside it, so it’ll be easy to just pick up a shirt and show him how soft the fabric is. Now would be a great time to say something like “this would look so good on you” or “this shirt would totally show off your arm muscles” or even “you’d look so hot in this,” then your next sentence should be “will you try it on?” followed by a cute head tilt and eye flirt – you know how it goes.
Third Step: Once you get him in the dressing room it’s a piece of cake. He comes out in the outfit and all you have to do is turn on the charm. You know him best, so just use your best flirt technique to show him how much you loooooove how he makes that shirt look. It’s not the clothes you like, it’s him….in the clothes. Then when he finds out that he actually also likes the way he looks – because clearly you have impeccable taste and wouldn’t put him in something terrible – it’ll be a lot easier to get him to try the same shirt in a different pattern, or maybe something else that he wouldn’t have picked out himself. It also doesn’t hurt to grab your own stack of clothes for him if he’s picking out stuff as well. That way he has some stuff that’s outside his comfort zone and probably at least one of your picks will make it to the register.
Make sure you don’t override him and wax poetic about something he clearly hates or is uncomfortable and he’ll never wear. It’s about a little wardrobe enhancement, not the time to pick apart his style or make him feel bad about his current clothes. With a little girlfriendy flirtatious encouragement, you’ll start seeing a gradual improvement in your guys’ wardrobe. Honestly, if all else fails, just start buying him things to wear if you’re tired of staring at the same three graphic tees. Happy shopping!