Matzo Ball Billiards

Howdy, fellas. Let me preface this piece by assuring you that I am by no means an expert on men’s fashion. With all the humility I can artificially muster, I must insist to be just a lone traveler, moseying along on my own style journey. That being said, I think I’ve learned a thing or two about a thing or two that I felt were worth rambling about.

Let’s reintroduce the big question by paraphrasing the title. Why is it that men often fail during their first attempts at improving their personal style?

I saw a tweet a while back that said something to the effect of, “Whenever a guy tries dressing better for the first time, they inevitably experience a period of time where they end up dressing worse than before they made this attempt.”

Reading that, I recalled (with an ounce of PTSD) my earnest, yet painful attempts at “prep” back in high school. The thin Aeropostale cardigans I wore, for some reason, over a crew neck sweater. The questionably tight, fire engine red, polyester pants from the Zara discount rack I occasionally sported during my gap year, and other forms of self-hatred in the form of “fits that go shart.”

But I’m not alone in this experience. Many men simply don’t get it right on their first try. Or their second. Or ever (Lord, have mercy on the souls of the eternally drip-less).

I’d attribute this to three primary causes.

1. A Ton of Online Menswear Content Is Just Plain Awful

This one’s pretty simple. There’s no shortage of online inspiration for men’s fashion, but there is a shortage of good inspiration. A lot of guys will turn to social media like TikTok, Instagram, or even Pinterest for ideas. There’s good stuff on all of them, but the worst corners of these apps are strongholds of normie-culture, the kinds of places where this stuff is championed as acceptable without protest:

It’s… it’s not great. It ain’t good. No siree.

Guys see this stuff and for some reason, a lot of them think it looks neat. It does not. I retract my earlier statement. I am the authority here. Do not dress like this, please.

A quick google search of “men’s fashion inspiration” will likely yield similar results. Terribly tight fits. Printed, stretchy suits with poor pattern-matching on the seams. So much synthetic material that you may as well be wearing a deluxe set of Tupperware.

Because this content is often the first stop you’ll come across, the surface of the “menswear iceberg,” if you will, a lot of guys fall for it. I know I have. But this shit puts bad ideas in your head. Ideas like, I think I will buy a suit…from Shein.

Do not do this under any circumstances.

It often takes a bit more digging to find decent menswear influencers, blogs, twitter accounts, etc. But the surface of the sea of menswear content is choppy and tends to lead fellas astray for a while. If they’re lucky, they find their way back to the trail, maybe a little worse for wear (hehe).

But there’s still another common obstacle.

2. Prioritizing Quantity Over Quality

Somewhere along your journey, you’ll begin to pick up on the “buy less, buy better” mantra. This is pretty sound advice for a couple of reasons.

For one, it’s better to curb rampant consumerism where we can, but it’s not just financially healthy to make smarter purchasing decisions — you’ll also probably end up happier with the things you do buy.

What’s better: Buying three pairs of cheap pants you kind of like but not really, or one higher quality pair that you absolutely love?

Say you could get all four pairs. I’d bet my kneecaps you’ll opt to wear the ones you really like 90% of the time while the others languish in a drawer.

For some reason, it takes a while for this mindset to set in with people, especially when they’re eager to experiment with their style. Excited to try out a new look, they’ll flock to their preferred fast-fashion store at the mall or online titan like Shein to go on a shopping spree. They pick up a fresh batch of tees, a couple of pairs of jeans, some rayon camp collar shirts, heck, maybe even some pleated trousers if they’re on the right track, and more, all for the surprisingly low cost of $200 and some unregulated child labor.

Look, ethical consumption is a tricky topic, and one I have yet to fully grapple with myself, but the current point still stands — that the current fashion landscape makes it pretty easy to get a lot of clothes at once for pretty cheap. The only problem is, these clothes tend to be very poor quality, with the worst offenders falling apart or suffering massive shrinkage after only a few wears or washes.

The results? Dudes looking to “upgrade” their wardrobe end up with a ton of clothes that don’t fit well or are otherwise unflattering due to poor construction or materials, all because they went looking for it in the wrong places. And I don’t entirely blame them — at the end of the day, the average person will find themselves more enticed by a cheaper price tag. It isn’t rocket science.

But I’ve found that the alternative, while initially difficult to abide by, eventually delivers better results and higher satisfaction.

I’ll always recommend people to buy the best that they can afford — product depending, of course. There are exceptions, where sometimes a cheaper product really is a great bang for your buck. But prioritizing quality over quantity when choosing an article of clothing results in a wardrobe of things you actually love and want to wear.

But this spiel is getting long. Let’s wrap it up with point #3.

3. Lack of Attention to Detail

It takes time to learn the nitty-gritty stuff. A lot of guys find their initial inspiration to “dress better” in the iconic styles of their favorite characters — especially the ones they think look badass. Tony Soprano, Tommy Shelby, Patrick Bateman, Ryan Gosling in… literally anything (Mostly Drive and Barbie these days).

The thing is, there’s all these little nuances that go into what makes any of the aforementioned characters look the way they do. Patrick Bateman wears a suit, exemplifies the excess of late 80s yuppie culture, kills people — and yeah, he looks pretty damn sharp doing all of it.

But what a ton of younger guys tend to end up missing is that it isn’t just the fact that Bateman wears just any old suit that makes him look the way that he does. There are a lot of suits you can go out and buy, and many of them aren’t great.

Bateman spends half of both the movie and the book (obligatory “the book is better”) obsessing over his designer wardrobe, and while the exact vintage Armani set might prove too difficult to track down, those generic navy suit separates from your local department store aren’t going to achieve the right look either.

It’s definitely not all about brands. A lot of factors can be missed when you just look at a suit as just a suit, pants as just pants, etc. Are the pants cuffed? If so, how much? What kind of lapels do you prefer? What rise on pants is the most universally flattering? Is a spread collar shirt really the best option?

It can take a while to pick up on all of the various important distinctions that make up an article of clothing, and that’s okay. I learn new things every day — but only because I’m paying attention. And that’s what more guys need to do the next time they set out to pull up to the office dressed like J. Robert Oppenheimer. They need to be looking for the small things, the ones that actually make an explosive impact (hehe).

Closing Note

Again, I’m by no means a true expert on menswear and there are many days where you’ll catch me rocking some ill-fitting chinos from college and a synthetic sweater, but I do care about clothes. I think I’ve come a long way on my style journey and wanted to share some of the things I’ve picked up along the way. I hope they’ve been helpful!

Thanks for reading 🙂