About a month ago, I got an email from a guy named Mike in Cleveland that made me want to throw up in my mouth a little bit. He’d been reading men’s style advice religiously for the past five years. He’d spent probably upwards of $3,000 building out his wardrobe. And yet he still felt…basic. Tons of blue OCBDs, gray chinos, brown leather shoes, “neutral” shirts. You know the photo I’m talking about because it’s the photo every man sends me of his closet. (Hint: it’s basically mine from three years ago.)
Seeing Mike’s closet sent me down a rabbit hole of thinking about why I’ve become steadily disillusioned with the majority of men’s style advice out there…including things I used to write and recommend. Because here’s the thing. Most style advice is either completely oblivious to how most men actually live their lives, or is consciously trying to make dudes dress worse.
That’s right…I said it. But hear me out. I know, as a guy who literally gets paid to write about clothes and men’s style, this is gonna sound weird coming from me. But a part of me feels like it’s my obligation to say something, even if it means putting my head through a guillotine. Because too many people have asked me for style advice who’ve religiously read every single “essential” list out there, poured thousands into a closet full of completely wrong recommendations from supposedly reliable sites…and yet none of it actually served their life.
Why? Well buckle up.
Clothing advice for men assumes you live a fantasy life.
Flip open any men’s magazine, read the table of contents for any major menswear blog or newsletter. What you’ll notice right away is how oddly specific they are in assuming what kind of life you live. Go to business meetings you need that navy blazer? Cocktail party on Saturday night? Date night Sunday? You guessed it – you need a tuxedo too! Safari adventure on Wednesday? Yup, they’ve got you covered.
Here’s the problem though – how many of us actually live lives where all of these scenarios play out with any regularity? Hell, how many of us can afford to live like that? It’s fine to publish articles about “building a versatile capsule wardrobe,” but when your definition of versatile fits about 5% of the people reading your article, maybe we need a better word than capsule.
Take the navy blazer – the holy grail of every “what every man should own” article. I owned three blazers at one point because I kept reading about how essential a navy blazer is. Let me tell you how many times I actually wore a blazer in a year? Exactly twice. Maybe thrice if you want to gettechnical. I felt overdressed whenever I wore one. In my office? It’s not typically necessary. Every single article assumes you work in finance or a stuffy corporate office. If you work in technology, education, service industry, healthcare…or any postmodern industry where your office looks more like a start up than Mad Men, you aren’t going to wear a blazer much. Hell, I know engineers who haven’t worn a suit jacket at work in a decade. It’s just not essential.
But articles continue to recommend blazers as if they’re the second coming because adult male society they’re referencing doesn’t actually exist anymore. A few weeks ago I went through 7 separate “10 essentials every man should own” articles and highlighted how similar they all were. Every single one? Weatherproof outerwear, dark jeans, a white dress shirt, and brown leather shoes.
See anything weird about that list? Not one recommended athletic wear of any kind. And if you know guys at all, we probably wear t-shirts and sweaters more often than we wear dress shirts. But nowhere will you see a well put together graphic tee on one of these lists. Only two of the articles mentioned outerwear that would actually keep you warm. Try wearing a bomber jacket in Chicago when it’s snowing, you’ll literally freeze to death because you won’t listen and buy a heavy coat. Not one article mentioned boots, even though every fall and winter guys desperately search “can I wear boots with jeans?” on Google.
So what’s my point? Too much advice assumes you’re a White, upper middle class man who works in finance or law, goes to cocktail parties, occasional weddings, and probably still gets dressed by his mom on special occasions. It’s utter garbage.
Clothing advice for men is really class signaling advice.
Look, I’m not saying know your seasons, own some white shirts, and have pants that fit are bad things. Hell half my closet still falls into that “traditional” style of dressing. But too much menswear advice frames these items as “necessary” for some archetypal version of a man.
Did you know that rolling your shirt sleeves is actually “wrong?” That you shouldn’t wear v-neck shirts with jackets? That you should always tuck in your shirts? There are entire blog posts written about how to correctly fold your pocket square. What’s my issue with this type of advice? Unless you’re running around campus pretending to be a member of the Queen’s Guard or teaching old style memes new tricks, nobody cares.
In fact, the majority of this advice is just class signaling. Learn to properly construct a lapel. Learn what Goodyear welted shoes are. That big shirt collar is “incorrectly” worn by half the population – here’s how you SHOULD fold it up. Do you know what none of that has to do with? Looking good. It’s literally men’s style advice saying “if you dress like this, you can sit at My Table.”
We even police one another about how we wear these supposedly symbolic details. Not enough hipster intrigue in the roll of your shirt sleeves? God forbid you wear a button-down with jeans. All of a sudden you’ve ruined clothes that were made perfectly suitable for jeans fifty years ago. Want to wear a sweater with your suit? You’d better let those suit shoulders peak out over the sweater like some sort of suedeanned Segway.
Too much style advice assumes you’re rich or will become rich.
Look how those guys above dress. Now tell me how you dress on a daily basis. Gotch ya. If you want to look good in clothes, money definitely helps. Things that fit well and are well-made almost always cost more. But guys have told me they looked great in thrifted suits that cost them $45. I’ve seen people look absolutely horrendous in brand new $300+ outfits I could afford. Advice better save you some cash.
We know the stats – it takes men upwards of FOUR times as long to spend their first $10,000 than women do. You know what the #1 question I get asked in my Style Consultations? “How much does this cost?” Look, if someone comes to me and says they want to learn how to dress well but can only spend $500 on clothes a year, I will happily give you a list that’s 90% thrifted items. Conversely, if someone emails me and says they make $450,000 a year and don’t know where to start with clothes, I will adjust my recommendations accordingly.
Color coordinating your leather? Seriously? Odds are if you have to ask that question, you’re not actually buying $800 shoes that need coordinating anyways. Hell, when I first got into dressing well, I couldn’t have afforded those shoes. But I wasn’t rich. I worked my ass off, lived in cheap-ass apartments in rough neighborhoods, dated terrible women, and slept on the couch of friends until I reached a point where I could buy something nice without selling a kidney. Advice should empower your goals, not set unrealistic monetary expectations for you.
Clothing advice for men is stuck in the past.
If you want to see how little menswear has progressed as a whole you only need to look at one person. Don Draper. The man has somehow put menswear into permanent stasis.
Everywhere else design is innovating, going forward. But men’s style advice? Still so “minimal.” Guys change clothes before dinner like we’re going to a wedding every time we leave the house. Hell, I’ve seen button down shirts this goddamn century referred to as “business casual.” Wearing a pocket square to work? Guy’s still getting sent home in Made In Chelsea.
Modern men’s style advice insists we live in the early 1960s even though most dudes weren’t even born yet. Get into an office where most of your coworkers have overt personalities and you’ll find pockets upon pockets of men trying to enact a quarter century of lifestyle advice onto their lives.
Want to know how dated menswear advice is? Try Googling “should I wear different shoes for day and night?” and watch the ridiculous amounts of yes articles pop up. Nobody cares. Not one company requires different shoes for day and night meetings. When did this even become a thing?
Clothing advice for men assumes there’s only one correct way.
Did you know that how you angle your shirt sleeve can be correctly or incorrectly worn? That how high you tuck your shirt in somehow makes it either right or wrong? That how you fold your pocket square is a TRUE or FALSE question?
Style is subjective. Full stop. But telling you that how to fold your pocket square “actually works” and how you probably fold it is “wrong” implies there is some magical standard for dressing well that we all must uphold. Newsflash – there isn’t, and that standard probably comes from Big Pink himself.
Way too much men’s style advice treats style like a problem to solve. Here are the rules. Here’s what you SHOULD be wearing. Here’s what you SHOULD NEVER wear. Ever. Follow this guide, and theoretically, you’ll be “doing it right.” Sure, following all that advice will help you put together very well put together outfits that are “correct.” You probably won’t have any style. Style is an expression of your personality through clothing. It cannot be produced purely by checking items off lists.
Okay, so style advice sucks. How the hell do we fix it?
Great question! One I spent years ignoring until Mike from Cleveland showed me his closet. Here’s what I’ve learned to filter good advice from bad.
Ask yourself where every style article you read is actually coming from. When you read an article about how to dress well, ask yourself these questions:
* Who is this advice actually written for?
* What kind of life does it assume you lead?
* What class does it expect you to come from?
* What social group are they trying to let into “The Club?”
A lot of style advice makes TOTAL sense when you realize the specific place and time it applies to. Salesmen going door to door in suits? SUUUUPER relevant that their jacket sleeves match their pants’ leather trim. And? Who cares if your office doesn’t have that rule? Learn it. Then forget about it and move on when it doesn’t apply to your life.
Remember how I told you to identify what type of style advice you were reading? Here’s where that comes into play.
Okay, so now that you have a better understanding of what advice to follow. How do you actually assess if advice is any good?
Do you know what will never go out of style? Solutions that work. Articles teasers about DON’T DO THESE THINGS stains the fabric of our being. If following a piece of style advice makes you look and feel good in your clothes, it’s probably something you should keep doing. It doesn’t matter if it “breaks every rule” known to man. It works for you. That’s all that should matter.
I’ve started asking my customers this question when they inquire about my services: If you could pick the brains of anyone living or dead about style, who would it be? I’m consistently blown away by the answers I get back. Guys who think like costume designers when they approach clothing. Guys who’ve learned how to bend “the rules” without breaking their look. Hell, I learned more about dressing well from watching Drake’s Dressing Room than I did reading Menswear Style blogs for years.
The more you expand your resources, the better you’ll start to understand what works for you and what doesn’t. Too much of the style advice our generation consumes comes from one major niche: White, upper-middle-class American or European society. Our understanding of how clothing works will only improve when we start looking at how other people exist in their clothes. Yes, there are “universal” truths to wearing clothes. But not everything works for every body.
Remember how I said I asked Mike what his life actually looked like? His hobbies, job, routine, all that good stuff. He sent me pictures of guys he actually admired style-wise. Hell, he sent me pictures of outfits he wore that made him feel really damn good. The more we can ground clothing advice in the reality that clothes actually exist to serve YOUR life, the better we’ll all get at giving (and taking) that advice.
Use your life as a filtering measure for clothing advice. It works for films. Does blithely following every style article on the internet help you wear clothes that suit your life? If not, it’s not helping you.
Shop Your Values,
Jake Ryan
