How To: Clothes the Chapter on Bad Wardrobes

I'M BACK! Sorry for the delay. I have had a wee bit of a rough week. But better late than never, right? I am slightly guilt-ridden about my post this week because of how unbelievably awesome Chris keeps proving himself to be. To say I was under the weather this week would be an understatement and my dear boyfriend bent over backwards to make sure I was okay, even when I was puking and whiney. I was pretty positive that was when only your mom still loves you, but alas, Chris prevailed. Thank you so very much for that. You're the best!

You know what he's not the best at? Dressing himself. Holy moly. If you ladies have ever met your boyfriend somewhere only to find them wearing something completely atrocious you're wondering how they ever even thought they looked okay, go ahead and click JOIN THIS SITE. Yep. Its happened to us all.

This is a serious dilemma, ladies. There's no nice way to be like "Honey, I love you, but you dress like crap." Like almost every guy I've ever met, he's not so keen on shopping. If it can't be accomplished in less than 10 minutes, the look of pure misery slowly creeps onto that cute face of his and he suddenly turns into Oscar the Grouch.

I'm also not willing to spend money on new clothes for him that I'm not entirely positive that he'll actually wear. So I needed to figure out a way to rope him into deciding for himself that it was time for new clothes. This was one of the trickiest things I've ever had to figure out - I'm not usually one for conniving behavior, but it was time to figure out a plan.

Let me frame the situation for you. Chris is a victim of baggy clothes. First off, boys, baggy clothes do nothing for you. You know when you see girls that wear clothes that are too tight and you're like "WHOA, not good", baggy clothes have the same effect for you. You look like you either just lost a ton of weight and refused to buy new clothes or have been single for entirely too long. Now, by no means turn this advice into wearing t-shirts so tight that your "muscles" look bigger. Nope. Uh-uh. Don't do it.

I knew from the beginning that helping Chris's wardrobe was going to be a multi-step process. A complete overhaul is enough to stress anyone out, so how to do this as gently as possible? An opportune moment arose a few weeks ago when Chris forgot to grab a belt to wear with his shorts. (First off, if you HAVE to wear a belt, your clothes are probably too big.) This was my moment. It was time to seize the opportunity. As the day went on, Chris became more disgruntled with his shorts repeatedly falling down and having to hike them back up. I finally asked him if maybe he needed to get some new shorts that fit a little better? The seed had been planted.

The next day, Chris showed up at my house ready for a 10-minute-or-less trip to the nearby outlet mall to buy some new shorts. We left J Crew with THREE pairs of new shorts (all exactly the same but in different colors - this meant he only had to try on one), and on the way out, I was so excited, I took a picture of the back of Chris with his stupid baggy shorts. I quickly showed him how they were entirely too long and how dumb they looked from behind. What do you know?! I haven't seen those awful shorts again. 

In the car on the way home, I jokingly said, "YAY! You'll look so much better! Now we need to just work on your shoes next." He immediately looked down at his shoes, and didn't say much else. 

Two weeks later, I received a text message that made me nearly jump for joy. "Okay, lets find me some new shoes this weekend." I nearly fell out of my chair I was so excited. I automatically assumed that his old, worn-out tennis shoes had, in fact, fallen apart prompting this text message. Turns out, after just my little comment about shoes being next was enough for him to notice his shoes for the first time in probably 10 years (when he more than likely bought them). 

That Sunday, we made a trip to the nearest DSW and picked out some new shoes for him. As we were checking out, I grabbed two sets of new socks for him and told him he needed those too. He laughed, and as he was checking out, the girl looked at him with an adoring look on her face and goes, "I am so proud of you for buying new socks, too. No point ruining new shoes with the wrong sock choice." Chris blamed it on me, and the girl looked back at him and goes "You know what that makes her, right? A keeper. And she's cute too, don't mess this up." I just stood there with a smug look on my face and walked out to the car.

As we got in the car, I looked at Chris and said, "Well, are you going to put them on or what?! I'm so excited to see them on!" He started to put them on with his old socks and I just stared at him until he switched to his new socks, too. I then repeatedly complimented him on his new shoes and how awesome they looked, and said "Now we just need to get you some new t-shirts!"

The funniest part about this whole process to me has been the feedback I've gotten from girl friends of mine and even my sister-in-law. So many people have been like "Okay, HOW did you get him to get new stuff?!" Everyone seems to laugh hysterically at the fact that I did, indeed, take a picture of Chris from behind to show him how unbelievably ridiculous his shorts were. So how do you go about suggesting that your significant other work on their wardrobe?

1. Take it one step at a time. Especially for boys, pick one area to target. They're more likely to go along with it if they're only shopping for one thing at a time.
2. Nagging will get you nowhere. Find a way to plant the seed and then DROP IT. (ex: Chris's  no-belt dilemma).
3. After you've convinced them to change whatever it is thats awful, let them pick their own alternative. You are there to guide them - but it has to be their decision as to what they end up with. So suggest the correct colors/styles, but leave it up to them.
4. Implement rules once new items have been purchased. Chris's old shoes are to be Yard Work Only shoes. They're in my garage, because I'm the one with the yard.
5. Don't try to force anyone out of their comfort zone. No matter what you tell me, I'm never going to wear skin tight skimpy clothes, so I can't expect my other half to show up in seersucker and a bow tie. It won't happen. Thats not Chris, and I'm good with that. 
6. Guys are all about comfort. If they even THINK something might be uncomfortable, they're more than likely going to act like a 4-year-old and not even attempt to try it. Find an alternative that completely proves them wrong and work that angle instead. (Ex. boys who wear "shower shoes" instead of proper sandals like Rainbows.)
7. Compliment them like crazy when they do follow the "rules" - positive reinforcement will go a long way. 

To all of the dudes out there, we're just trying to help you. Don't you love having a hot girlfriend? We love having hot boyfriends, so bare with us. This is one area where you should be glad we know more than you. 

Look at how proud of his new shoes he was.
One small step for Chris, one giant leap for his wardrobe.

Chris - I love the crap out of you, holey t-shirts and all. Don't worry - we'll fix that next.