The New Rules Of Shopping For Men

My obsession with clothing is something I’ve always had within me. It didn’t come from my dad or my blue collar upbringing in Cleveland, Ohio. I grew up fascinated with how clothing can tell stories about people, how style can speak about your personality, your background, your profession, or your outlook on the world. It can do so loudly or in a subdued way so only those who know, know. I know — I have made style my life’s work, working in the fashion industry and building up A Continuous Lean, a newsletter, blog, and social platform that follows the ins and outs of the men’s style industry.

Do I know everything? Of course not. But I am in a position to offer some advice. One thing I’ve found over the years is that the majority of men struggle with shopping. Or, more accurately, struggle to find the motivation to shop. Clothing isn’t life or death — or raising children for that matter. Who has time to shop for clothing for yourself when you’re trying to get the little ones dressed and out in the morning? It can feel selfish and like a poor use of time when you’re trying to manage it all. Between work, family, and fun, who has time to focus on getting dressed? Besides, when it comes to men’s style, there are so many rules, spoken and unspoken dress codes that feel at best like another chore and at worst like a sort of Big Brother there to keep your clothing choices in line.

The many so-called rules of men’s style have been thrown into such disarray it’s hard to know what to think about dressing oneself.

There was a time when men’s magazines acted as judge, jury, and executioner — laying out the style rules for men, scolding us when we were breaking them, and telling us exactly how to build a wardrobe. The advice usually sounded something like this: Buy a navy suit and a gray suit. Two white shirts, a blue shirt, and a blue striped shirt. A pair of black lace-ups and a pair of brown loafers and that was it. If that sounds like the 1950s, you’re not wrong. Sure, the editors taught us about the quality of the material — Italian merino wool, man! — and to appreciate the cut and craft. The fetishization of materials and make, of the craft and skill within the textile industry, was an important lesson. But the overarching look? If you boiled it down, so much men’s style writing was a dream of Don Draper that connected with people’s actual lives about as much as a three-martini lunch.

Such advice has never felt more irrelevant. Anyone who has been in public recently understands how style is different now. With the last two years of video conferencing and WFH, the casualization of the world has advanced so much that the concept of suits and dress shirts is almost unrecognizable. The many so-called rules of men’s style have been thrown into such disarray it’s hard to know what to think about dressing oneself. With no standards, who is to guide us?

We can now dress like the most authentic version of ourselves in our authentic surroundings.

Scott Pyburn, the owner of one of my favorite stores in the world, Harrison Limited in Mountain Brook, Alabama, has a pretty good idea of where to start. “The important thing is you have to have confidence in what you are wearing,” he says. That’s why “when a customer comes into our shop, the first thing I ask is about their work. ‘Tell me about your work. How long have you been there? What does everyone else do there? What is the dress culture?’”

In other words, we can now dress like the most authentic version of ourselves in our authentic surroundings. Just look to Donald Glover, David Beckham, or, hell, Dwyane Wade. These men, these dads, face more public scrutiny than you or I ever will, and not one of them conforms to a look, a standard, or a rule.

Of course, this doesn’t mean we should lose sight of the goalposts — the understanding built into men’s style that the craftsmanship and design sensibilities behind clothing should get as much thought and reverence as the 2022 Porsche 911 GT3. That’s to say there’s no incorrect way to dress, but there is a potential to be a bad consumer. Making smart purchases, buying for value, and having a uniform that feels good and represents you is the final frontier of personal style. Those are the tenets by which I personally operate. I care about how something is made, who made it, and how it fits into my closet for the long term. When I get dressed in the morning, I have little doubts about my clothes — and that makes all the difference

My “Rules” For Dressing In The Real World

There are no rules but your own. Here’s what helps me navigate a store and to get dressed in the morning. Take this all under advisement — and don’t hesitate to ignore what doesn’t work for you. Freedom in your look is, after all, the point.

1. Observe Your World. The first thing you need to do is make some observations. Look around at work or in your personal life (or just find someone on Instagram) for someone who dresses the way you want to, and start there. It’s also important to think about what you do for fun or work, it will influence what you wear and how you shop.
2. Skip The Trends. If you don’t have strong opinions about your love of vintage, Western workwear, or designer fashion, go for classic items and skip the trends. All those photos of Steve McQueen are kind of played out at this point, but his style endures for a reason — he favored the classics.
3. Build A Uniform. Observations about the world and who they aspire to be are what help people figure out how they look the best and have the most confidence. That’s how I developed my own uniform. I started to take note of stylish people in my everyday life who I aspired to dress like. I also paid more attention to what I felt confident wearing and went all in on those items. A specific example is unstructured sport coats. I realized that they are comfortable and versatile and really help to elevate my appearance everywhere, be that at a meeting or a dinner. This realization made unstructured jackets part of my permanent rotation, and it made packing or deciding what to wear to an event so much easier.
4. Trust Your Grandfather’s Style. A company that has been making something for a long time, through multiple generations, is still in business for a reason — it makes a great product. Heritage brands are special and should be treated as such.
5. Know When To Stop. If you find your favorite version of something, call it quits. Just because there are a million brands in the world doesn’t mean there’s anything wrong with only wearing five to 10 of them. Kamakura is my go-to shirt maker, so that’s where I buy all of my button-downs. Crockett & Jones makes my favorite leather shoes. I’ve found the perfect brogues from the brand, so I don’t need to keep looking.
6. Avoid Consumerism. American culture is gaming you for maximum consumption. Don’t be motivated by the false urgency of sales, and don’t shop because of boredom. Part of this supercharged commercial culture means that there are so many hyper specific brands launching every minute that it's all overwhelming. Here’s a shirt which you only wear untucked! Or this one is meant to be tucked in. What happened to just buying a regular shirt? Instead of following trends, do a little research, find what you like, and buy it. If you like it, stock up. If we all did this, Black Friday sales would be extinct — and we would be better dressed for it.

Michael Williams is the founder of A Continuous Lean, a newsletter, blog, and social platform that follows the ins and outs of the men’s style industry.