Smitten

A Guy Explains: How to Help Your Fashion-Challenged Man

It's almost a universal truth that when a poorly dressed guy gets into a relationship, suddenly he starts dressing better. The football jersey, baggy cargo shorts, and Teva sandals are replaced with fitted jeans and a crisp button-down. And it's no mystery as to who the architect is behind this transformation. For the past 50 years or so, it's been wives and girlfriends who have done much of the heavy lifting when it comes to keeping men fashionable. But it wasn't always this way. The modern male's inability to properly dress himself can probably be blamed on the hippies. Seriously. Until the flower-power revolution of the late 1960s, it was much more common for men to care about how they looked. The world was full of Don Drapers (we're just highlighting the fashion here, not the culturally imbedded misogyny): men who wore crisply tailored suits with cuff links and pocket squares. But by the late 60s, the male half of the species turned into Stan Rizzo, badly dressed sartorial comfort seekers who never came within spitting distance of a suit or tailor they liked. And since men often learn how to dress from their fathers, we've been stuck in this

It's almost a universal truth that when a poorly dressed guy gets into a relationship, suddenly he starts dressing better. The football jersey, baggy cargo shorts, and Teva sandals are replaced with fitted jeans and a crisp button-down. And it's no mystery as to who the architect is behind this transformation. For the past 50 years or so, it's been wives and girlfriends who have done much of the heavy lifting when it comes to keeping men fashionable. But it wasn't always this way.

The modern male's inability to properly dress himself can probably be blamed on the hippies. Seriously. Until the flower-power revolution of the late 1960s, it was much more common for men to care about how they looked. The world was full of Don Drapers (we're just highlighting the fashion here, not the culturally imbedded misogyny): men who wore crisply tailored suits with cuff links and pocket squares. But by the late 60s, the male half of the species turned into Stan Rizzo, badly dressed sartorial comfort seekers who never came within spitting distance of a suit or tailor they liked. And since men often learn how to dress from their fathers, we've been stuck in this generational cycle of bad style for nearly half a century now. If not for the efforts of wives and girlfriends, who knows what sort of bleak, jorts-filled world we'd be living in. But, as with anything, there is always room for improvement. Here are four ways to gently, kindly steer the man in your life in the right direction:

Focus on Fit:

Throw a perfectly fitted T-shirt and jeans on a man and it will look better than a poorly tailored suit 100 percent of the time. The problem with a lot of guys is that they associate "well dressed" with what they are wearing rather than how they are wearing it. Just look at David Beckham as an example of how to do it right. He can rock a simple polo shirt and jeans and still look better than 99 percent of the male population. The key to it all is fit (well, and to look like David Beckham, but never mind that). Excessive fabric is the death of style. Paul Ryan and his tent-like suit monstrosities are all the proof you need on this. So, when it comes to improving the style of your man, find a good tailor and then keep drilling this mantra into his head: FIT, FIT, FIT.

Match His Personality, Not Yours:

I will occasionally notice this: A poorly dressed guy will begin dating a woman who lives on the extreme end of the fashion spectrum, and suddenly we see a software engineer who looks like he mugged Sid Vicious. The important thing to remember when sprucing up your man is that he isn't a mannequin. Think of dressing him as a team effort: You have all the fashion know-how, he has the specific personality, so bring those two together. Most of the time, that means landing somewhere in the middle of the fashion spectrum. Cary Grant, possibly the most stylish man ever to walk the earth, summed it up perfectly when he said, "Simplicity, to me, has always been the essence of good taste." [LINK: http://www.gq.com/style/wear-it-now/201304/cary-grant-and-todays-style#slide=1] So consider how to reflect his inward personality with his outer style. What you'll end up with is a stylish man who is wearing the clothes rather than a man who is letting the clothes wear him.

Don't Forget the Shoes:

I don't know what it is about guys and shoes, but, holy hell, they can't seem to put it together. The footwear horrors I've seen on the New York City subway are enough to keep a person up at night. And nothing will kill a great ensemble quicker than a bad pair of shoes. The biggest criminal offenders are square-toed dress shoes, dress shoes with seams running down the sides (for some reason there are a lot of slip-on varieties of this), excessively pointy shoes, and sandals. If your man is wearing any one of these abominations, chain him to the radiator until he comes to his senses. The best thing you can do when it comes to footwear is to steer him toward the classics. Some casual examples include Adidas Stan Smiths or Converse Jack Purcells. And when he needs to dress up, Italian oxfords, brogues, or wingtips are the way to go. If you're feeling slightly more adventurous, have him try a Chelsea boot, a wingtip boot, or even a classic pair of Red Wing Heritage Moc Toes. But whatever you do, for the love of God, make sure that he doesn't stop his style transformation at the ankles.

Pay Attention to the Details:

If you really want your guy to get his share of fashion compliments, turn his eye toward the finer details. Whenever I wear a suit or a blazer, the one thing I get the most compliments on is my pocket square. After that it's my tie bar. They're little things that a lot of people won't necessarily zero in on but will round out a man's look in a way that will set him apart from the herd: things like tie bars, pocket squares, surgeon's buttons (buttons that actually function) on the cuffs of his suit jacket, and collar pins. Similar to how women expertly accessorize an outfit, true style for a man is almost always in the details. The only difference for a man is that his style requires a bit more subtlety.

I admit, the past half century has been a bleak era for male fashion, but thankfully things are getting better. Thank you to the women in our lives for carrying us through the worst of it. With a bit of effort, even the most oblivious of jorts-wearing men can be saved.