MY THOUGHTS ON THE WALL STREET JOURNAL’S “ULTIMATE MEN’S PLAYBOOK OF STYLE DO’S AND DON’TS” AND OTHER PLAYBOOKS

A good friend of mine and subscriber to this blog sent me a recent article from the Wall Street Journal style section and asked for my thoughts. The article is titled, “The Ultimate Men’s Playbook of Style Dos and Absolutely Don’ts” by Jamie Waters. My eyes get wide and I go get a bucket of popcorn whenever I see a clickbaity menswear headline like this.

The article is self-described as, “A loose collection of rules, should have something for everyone, from tech bros to retirees to fashion snobs who pride themselves on correctly pronouncing the brand Loewe (‘Low-eh-vay’).” So…not really an ultimate playbook then, is it? Bravo, Jamie, you just admitted this is clickbait. In my opinion, the ultimate hardcopy men’s playbook is “Dressing the Man” by Alan Flusser, while the best playbooks in blog form (other than this one) are “Die, Workwear!” by Derek Guy and “Permanent Style” by Simon Crompton. These are three guys I look up to in the menswear space. Later in this post, I’ll talk a little about what to look for when deciding whose menswear advice you should heed.

As for this article, my friend mentioned, “It’s cool to see some of the stuff you say in it.” There are a few pointers I agree with.

• “Your clothes should fit,” and, “because many items don’t fit neatly off-the-rack, stylists recommend having a local tailor tweak them.”

  • However, I disagree from Jamie’s take that fit is the “top style rule for men.” Frequent readers of this blog will know the only thing I think that is more important than fit is utility, as seen in my hierarchy of importance in putting together an outfit.

• In regard to what to wear for a Saturday night dinner date, Jamie asks a female New York City stylist. She says, “dress appropriately,” as she has noticed straight males often dress far more casually than the females they are with.

  • Again, this piece of advice can be found at the top of my pyramid regarding decorum. In short, be yourself and dress like you, but an elevated version of your unique style that demonstrates you put thought and effort into your appearance.

However, I disagree strongly with three of Jamie’s suggestions and the broader way of thinking.

One of the most famous dangly earrings in movie history. Rick Vaughn played by Charlie Sheen in “Major League.”

• While answering the question, “How can I inject some personality into my outfit?”, one of Jamie’s five responses was, “Not a dangly earring.”

  • I can’t stand lazy, blanket statements like this. I know plenty of guys who would or do look good with a dangly earring. I have a piercing (I used to have more) and for a time it was a dangly earring. It wasn’t “bad” and again no clothing is “bad,” but there is better. For me, I feel that a hoop or a stud works better. If I found a solid dangly earring though, I would absolutely consider. The issue here isn’t so much Jamie’s dissing of dangly earrings, it’s saying that NO GUY should wear a dangly earring. All it takes is one picture of the male celebrity of the minute to rock one before trend-obsessed men’s fashion writers get rock hard for the newest “it” accessory.

    Let me use a different example to make my point. In most cases, I prefer the look of roomier trousers with more drape over slimmer cuts (note: that doesn’t mean baggy). However, there are some guys who look better in a slimmer cut. I would never say, “Skinny jeans are bad and no guy should ever wear them.” It depends on the guy. If I was writing a piece for the WSJ, I’d suggest that guys with this build who are looking for that fit should consider these trousers. It is a blessing that we have so many options to choose from nowadays and the speed at which new styles and ideas can be shared. The curse is in how to not get swept up in or overwhelmed by the waves and how to apply it (if at all) to our own style. Everyone has a place, and so do many things.

• Later in the article, the author turns to a New York exec for his takes, so I can’t fault him for this next one. Robert Dahdah, a 57-year-old chief revenue officer at software company PTC, suggested, “lessening the distance,” style-wise, when meeting clients. He says, “If you show up in a suit and they’re in jeans, you might not have a great meeting.” 

  • I’m a believer in showing effort and elevating your own style for important events, whatever that looks like for each individual. That should be the focus rather than the clothes themselves—the thought and preparation versus the execution. For me, that’s a suit provided that its utility makes sense for the situation. For others, that may be jeans and a button down. But you can tell when someone is dressing in a costume, doesn’t feel natural, or didn’t put any additional time or thought into getting ready. Again, don’t let others dictate how you want to dress or make you feel bad for doing so. If they do, know that it likely comes from a place of their own insecurity.

• Regarding how older guys can dress in a cool way, Jamie says, “Forget about Cary Grant’s suits—yes, he looked wonderful but that was a long time ago, when men dressed up.”

  • That’s it, guys. Pack it up. We’re done with suiting and dressing up because Jamie says so. I said it earlier, and I’ll say it again — I hate these blanket statements. Maybe he needs to get out more, but I know plenty of guys who still get dressed up and look damn good doing it. Perhaps more guys would do the same if they had more reliable resources instructing them how to get dressed up and where to spend their hard earned money on a good suit. One piece of advice guys should consider is from Cary himself, featured in, “Cary Grant’s Guide to the Perfect Suit” from The Rake.

    “It isn’t only money that determines how well a man dresses - it’s personal taste. Because of the demands of my work, I’ve purchased dozens of suits over the years and they all have one attribute in common: they are in the middle of fashion. By that I mean they’re not self-consciously fashionable or far out, nor are they overly conservative or dated. In other words, the lapels are neither too wide nor too narrow, the trousers neither too tight nor too loose, the coats neither too short nor too long. I’ve worn clothes of extreme style, but only in order to dress appropriately for the type of character I played in particular films. Otherwise, simplicity, to me, has always been the essence of good taste.”

    Pretty sound advice I’d say, especially for guys who don’t wear suits a lot and only need one or two, or people who find it challenging affording one.

Elegance in the simplicity of how Cary Grant wore his suits

I find annual “menswear playbook” articles like this one from the WSJ fascinating—perhaps also a bit infuriating. It’s fun though to compare ones from the present to those from a year, five years, or ten years ago and see what has or hasn’t changed. However, I enjoy this stuff. Many of the guys I work with get overwhelmed by what to wear. The speed of trends and the digital wave of talking heads, influencers, celebrities, and brands trying to hit quotas doesn’t help.

So, who and where should you turn to? I think whoever you heed advice from and whatever playbook you subscribe to should stretch your imagination and make getting dressed a playful exercise, but this next part is the most important. Much like you probably have your own core values and a select few family, friends, or mentors to turn to for advice, do the same for what you wear. Take wisdom from different places, devise your own set of rules, and then follow advice from a menswear expert or a select few whose values align with yours. Don’t get wrapped up in whether or not they dress like you presently or how you want to dress eventually . They may look completely different from you, live in a different place, or have a different background, profession, or hobbies. While I think some similarities can be helpful, it is by no means necessary.

On the contrary, the folks you should take with a grain of salt and probably disregard are those who say specific looks or items (like dangly earrings) are “bad.” Also, if you look at their commentary over the course of years and there is no consistency in their takes or a lack of authenticity and ability to think for themselves, he or she is part of that digital wave trying to sell you something or accumulate clicks rather than educate. Don’t let them pull you under.