How to Tell Your Friend He Dresses Terribly

Image via Complex Original

Since the dawn of time, men have been blaming women for their problems. Our ancestors blamed everything from personal failures to crop failures on women. Don't be afraid to make like your divorced drunken uncle and construct a female bogeyman to advance your agenda. The next time your boy complains that he is having difficulty with females, point out that while changing his style won't necessarily get him laid, it couldn't hurt.

An asshole in a suit is still an asshole, so don't lie to your friend and tell him that a few changes to his closet can overcome his deeply flawed personality. But, if you catch him sitting around in his velour track suit bitching and moaning about the lack of ladies in his life, point out that changing his style could be a step in the right direction.

Make if clear to him that if he wants to have a better chance of scoring with the ladies, he should dress like he belongs in their natural habitat. Where do eligible bachelorettes hang out? At brunch spots where you don't have a reservation. At nicer bars than the ones you frequent. At clubs you can't get into. Perhaps if your friend stops dressing like a Denny's regular, he will be welcome in establishments that don't offer discounts on your tenth visit. Convince him that a change of style won't necessarily get him laid, but it could get him in the door.

There are some men who will be impervious to the female argument. Men with girlfriends may see no reason to change their appearance when they've already found a woman who will tolerate their slovenly ways. Some men who walk among us have no trouble getting laid regardless of what they wear. Here in Los Angeles, I have seen men wearing hibiscus pattern board shorts and puka shell necklaces with women seven times more attractive than your high school homecoming queen. Good looks are a blessing and a curse, and one of the negatives of being a beautiful man is that no one tells you when you look like an asshole.

So what's your next course of action? If your friend doesn't care about fashion, he might care about dressing like an adult. In the age of casual work attire, dressing like a grown-up is a nebulous concept. However, we can all agree that if a thirty year-old man is still rocking a Blink-182 T-shirt and camo shorts, he probably doesn't enjoy the respect of his peers. Convince your friend that dressing better is part of becoming a man.

Next time you find yourself and your poorly dressed friend in a classy establishment like an after work bar or a high-end strip club, take note of how the gentlemen are dressed. Conversely, if you find yourself in some heinous den of teens like a shopping mall or an EDM festival, point out the style sins being perpetrated by America's youth. Direct his attention to the kid at the gas station drinking a Big Gulp with that shitty look on his face and say, "Thank God we don't dress like that anymore, huh?"

If your boy has a Cro-Magnon streak, equating looking good with "looking like a man" may sway his fashion sense in the right direction. The damage caused by a lack of fashion sense can be counteracted by healthy dose of peer pressure.

If your campaign of psychological warfare against your friend's fuccboi tendencies fails, there is still one option left. It's not a particularly pretty choice, but if your boy is dressing so badly that he is hindering your personal swag, desperate men may have to take desperate measures. It may be time to buy your boy some clothes. 

Believe it or not, there is a way to go about this that doesn't make you look like a condescending douche. One strategy is to involve an accomplice. A courteous email to your boy's mom regarding accessories he might like for his birthday or conspiring with his girlfriend to help up his style game are both approved moves.

Another, much cheaper strategy is the more obvious route: Give your swaggy hand-me-downs that would look better on him than his current duds.  The hope is that this chambray shirt or slim-fitting pair of pants will create a style avalanche that will loosen his grip on his credit card and result in a massive influx of dope clothing in his closet.

You need to find an item that will turn heads and get him compliments left and right. We're talking about a piece that will make even his worst enemy look to him and say, "Hey man, where'd you cop that?" The best items are menswear grails that are really more like gateway drugs—the one simple upgrade that will convince him everything else he owns is utter trash. Tried-and-true pieces include the Engineered Garments Bedford Jacket or Acne Max jeans.

If you've attempted to use your friend's horniness against him, played to his desire for maturity, and even used man's innate love of free shit against him, and yet he still doesn't dress well, he may be a lost cause. It is understood that you can't make a man do something he doesn't want to do. This is true of boyfriends who aren't ready for commitment. This is true of alcoholics who would rather lose loved ones than get off the sauce. This is also true of guys who would rather spend their life looking like human garbage than put one ounce of thought into how they look.

Once you've gone through all of these steps and you still spot cargo shorts, socks with sandals, and ratty collegiate hoodies in your boy's arsenal, it's time to let go. Not everyone is ready to hear the good news about what's in this season or how the right belt can bring an outfit together. And that's OK. You did what you could. Now you just have to focus on bringing him out to the bar with you so that you look fly by comparison. 

Brenden Gallagher is a freelance writer based in Los Angeles. Send him stories of your attempts to converted the unfashionable @muddycreekU.