I received this email at 2:17 AM on a Wednesday. Subject line: “STYLE EMERGENCY.” Body: “My girlfriend’s brother is getting married Saturday. Just realised my brown wingtips are scuffed to hell.
Can I wear black shoes with a navy suit or will I be executed on sight?? ?” I chuckled to myself, bleary-eyed and half-asleep. I get emails like that all the time, from otherwise successful and accomplished men who are terrified of being outed as a stylistic fraud. Mortified by the potential of breaking some style “rule” that their grandpa drilled into them as a kid or some arbitrary directive they read in GQ six years ago.
Here’s the thing about guys and style rules… Most men know maybe three of them by heart (swatch your belt to your shoes! Don’t wear white after Labour Day!
Suits should always have a tie!) but they somehow think there’s a massive secret rulebook that everyone else has access to.
They spend their lives fearing accidental transgressions and style-related indictment from…who, the Style Police? Actual police? Brothers – let me let you in on a little secret… A lot of these rules were made up by retailers to move merchandise, decreed by old wealthy guys to establish their superiority, or were actually sensible guidelines that just don’t apply to the world we live in today.
But some of them are rooted in actual principles of proportion, harmony, and context that are still relevant. You just have to know which is which. So let’s break it down.
The rules that are actually worth following versus the ones you should boldly declare to hell with, right alongside your learned intimidation about style. Think of this as your Style Rule Amnesty. We’ll start with my gentleman in the middle of the night and his brown shoe conundrum.
Did you know there’s a rule that says you can’t wear black shoes with a navy suit? It’s true. Instead, you need brown shoes.
Why? So no one will know you’re wearing dress shoes and not boots. (Yeah, I made that explanation up too.) This rule originated in the U.K. as a clandestine class distinction (black shoes with your tailoring for city stuff, brown for country casual) but honestly…does it matter? America, 2024.
I have worn black shoes with navy suits and looked good. Modern rule: shoes should coordinate with your outfit in terms of formality and colour family. Anything beyond that is just pedantry.
Wearing white after Labour Day? Snobby tradition founded on clearly differentiating the haves from the have-nots. Trash it.
I wear white jeans all year round, even attended a Christmas party last year where my shirt fully contrasted my snowman jumper vest and some old geezer pulled me aside to scold me for “breaking the rules of fashion.” “What rules?” I asked him. He couldn’t tell me any. Here’s my favourite egregious and completely-made-up rule. “Your belt always needs to match your shoes.” Raise your hand if you spent way too much of your 20’s obsessively matching your belt to your shoes.
Me too. Dude belts don’t technically need to match your shoes, but they should be close in shade and weight. Harmony, not dictatorship.
I recently had dinner with a group of young Wall Street types and noticed one dude eyeing my outfit nervously. Blue suede loafers. Medium brown woven belt.
Yeah, he couldn’t hold it any longer. “Is that…against the rules?” He hissed, low voice loaded with judgment, as if we were discussing insider trading instead of footwear. “No,” I replied. “It’s just fashion. Relax dude.” Needless to say, he kept asking mestyle questions the rest of dinner – his eyes clearly opening to a new world of calculated style anarchy. The issue with most style “rules” is they’re treated as commandments when they really should be guidelines.
Follow enough of them and you’ll end up looking alright in most situations. But to truly understand style, you have to elevate your thinking. It’s the difference between memorizing math formulas vs learning how math works.
Let’s look at suits as an example. You know how people always nag about how there’s a million “rules” for wearing a suit. Only wear solids.
Always leave the bottom button undone. Don’t cuff your trousers. Match your belt to your shoes.
Sleeve must show ¼” of shirt cuff. You wear a skinny tie? Your suit jacket needs slim sleeves!
Tie can’t be wider than your lapel. The list goes on forever. Here’s the truth – some of these “rules” are rooted in principles of proportion, fit, and appropriateness.
Others are bullshit. Which is it? Here’s how I split the difference.
If it serves a purpose related to fit, proportion, or harmony, it’s probably worth considering. Suit jackets have a button removed on the bottom so that when you sit down, it doesn’t bunch up awkwardly like a superhero’s cape. Seriously.
Try it. Suit sleeves should show about ¼” of shirt cuff to create nice proportion and visual separation. Makes sense, right?
Those aren’t just rules, those are guidelines to help you look better. Everything else? Follow at your own risk.
The pocket square should never match your tie? Please. Go enjoy 2024,square-less.
Striped tie? Only wear it with a solid shirt. Again…please.
Suit manufacturers recommend the jacket sleeve match your shirt sleeve in weight and colour? Who cares if your tie is double-striped and your top shirt button is undone. Wear whatever the fuck you want, Amish guy who thinks shirts with sleeves aren’t actual shirts still hates on me for wearing a chambray shirt under a blazer.” I learned that lesson the hard way.
My first major industry event, I was so concerned with following all the rules that I basically wore a MenswearMan costume. Every rule steadfastly obeyed. I looked like a complete tool.
The coolest dudes in the room (networking powerhouses like the designer wearing trainers with his suit, or the editor sitting next to me with clashing patterns that actually worked, or the brand manager wearing cuffed jeans and a blazer) knew the rules better than anyone. And that’s why they could break them. Style is not about blindly following a list of commands.
Style is about mastering the few things that matter most, so well that you can bend and break any guideline without looking foolish. So what ARE the rules that matter? I’ll save you the stress of figuring it out yourself: Number one.
Fit is everything. Without question. Best suit in the world, fits like rubbish = crap outfit.
Cheap suit from Marshalls that fits you perfectly = infinitely stylish. There are no “rules” here, this is just a universal truth. Number two.
Know your context. Sure, there are certain situations that call for certain levels of dress. But outside of those extremes, you should feel free to dress with nuance and make it work.
Nothing will get you labelled as a “tryhard” faster than showing up under or overdressed for an occasion. Know your environment. Most men fail at this rule.
Number three. Invest in quality. Not brands.
Not price points. QUALITY. I own expensive shoes that autumn apart and cheap shoes that I can still wear years later.
Wear stuff that fits you, and will get better with age, not worse. You don’t need to spend a lot of money. Buy less, buy well made, buy timeless pieces that you can mix and remix forever.
This takes experience, sure. But once again, learn how to spot quality. This isn’t a rule, it’s a lifestyle.
See how those “rules” are different? They deal with the foundations of style and clothing: fit, context, and realistic expectations. Now for some rules I’ll happily let you break.
Shirts with sleeves still aren’t shirts? Fuck that guy. Pale blue denim isn’t actually blue?
Sure it is now. Bright colours aren’t “broken in?” Wear yellow and enjoy the compliments, dude. Don’t wear black with brown?
Depends what kind of black and brown you’re working with. The style icon I mentioned above rocking that black knit jumper with the tobacco brown trousers? He taught me that rule can be broken when there’s enough contrast and visual separation.
See the theme here? Most “rules” are made to be broken. I could go on all day… Pleats?
Were Satan’s underwear for a hot minute there. Nobody cares about that nonsense now. “Prints should never match” ? Learn about colour theory and retain some empathy for those who don’t.
White shirt under a white suit is a big no no ? Please wear that to your next summer wedding. Ask me for tips.
Can wear a denim jacket with a casual suit ? Sure, Kayne did it before you. You need 3 pairs of shoes “minimum” to be fashionable?
Negative buddy. I have one black shoe and rock new outfits with it daily. Did you catch how most of those “rules” I just tossed out are because someone thought of wearing that combination and were told “no” by someone older and more close-minded than they?
It’s a cycle that needs to end. Here’s how I learned to stop worrying about dumb rules and love style instead. Over the years I’ve interviewed dozens, if not hundreds of men who could legitimately be described as “well dressed.” From “Best dressed” lists to famous tailors to high society elites to casual dudes who’ve put more thought into their wardrobe than 99% of men.
Not one man pulls out their closet and thinks about what to wear in terms of rules. They think about fit. Are my clothes tailored to me?
They think about appropriateness. Is this too much? Too little?
They think about details. Is my jacket laid? Are my shoes polished? “But Robert,” you may be saying to yourself. “Didn’t a few of these guys mention some ‘rules’ to you?” Good point.
Here’s what they told me: “I know all the rules. But knowing how they apply to fit, proportions, and fibres helps me know when to follow them and when to break them.” There are no style police. Nobody is coming for you if your belt doesn’t match your shoes.
Hell, wear polka dots with plaid if it speaks to you. Just make sure your shoes are dressed appropriately for the occasion and aren’t falling apart. I had a friend over for dinner who’s a vintage clothing dealer.
I brought up this whole article and how I was thinking of it. He nailed it while we sipped whiskeys: “Style rules are like training wheels,” he said. “They help you when you don’t know what looks good on yourself yet. But you always have to take them off eventually, or you won’t actually learn how to ride a bike.” He couldn’t have said it better himself.
Guys who slavishly follow “the rules” of style always look like they’re trying too hard. And guess what? They probably are.
Rule follows will forever be trapped in a world of fearing style rules. Will they dress nice? Some of the time!
Will they feel consumed with anxiety over if their outfit is “right?” All of the time! Don’t be that guy. Instead, learn the rules like every other man does.
Figure out why they exist. Help them make sense to you by understanding why they work, and when they don’t.
Then toss them out the window.
I told my panicked midnight sharer that yes, he could absolutely wear black shoes with his navy suit. Especially since it was an evening wedding. He ended up sending me a picture from the wedding a few days later.
He looked great. Happy. Relaxed.
No style police came for him. “I got three compliments on my outfit,” he texted. “I can’t believe I stressed about this so much.” Because that, my friends, is what happens when you let style rules control your life. You spend way too much time worrying about things that don’t matter and don’t let yourself enjoy your outfits. Let’s change that.
Forget the rules. Learn style.
