I received this email at 2:17 AM EST on Wednesday. Subject: STYLE EMERGENCY Message: My girlfriend’s brother is getting married Saturday. I just realized my brown wingtips are worn down so badly they’re ruined.
Can I wear black shoes with a navy suit or will I be stoned upon arrival???? ? I stared at my phone screen in a haze, chuckling to myself. Guys send me panicked messages like this all the time.
Successful, stylish men who suddenly devolve into panicked undergrads because they’re afraid of violating some ancient style dictum their granddad passed down, or that they remember reading in GQ while flipping through magazines at the barbershop circa 2011. Here’s the problem with most men’s style “rules” – the average guy only knows about three of them (“Coordinate your belt and shoes!
Don’t wear white after Labor Day!
Suit= tie!”), yet assumes that there’s some secret handbook of style everyone else has access to. Who are they afraid of misstepping in front of? Jared?
Michael? Giovanni?? The guys who act like they’ve got rules tattooed on their foreheads will get you stressed out about things that don’t even matter.
What we need is a style version of amnesty for all these dumb rules. Let’s take my late-night requester, for example. Black shoes with a navy suit is a no-go, according to Old Fashioned Rules of Menswear.
Yet who cares? I’ve known plenty of guys who wore black shoes with navy suits and rocked them. The only “rule” that matters: Wear shoes that match the formality and color of your outfit.
End of story. Wearing white after Labor Day? Seriously?
Don’t sweat this total elitist fabrication. Those white jeans I wore to my Christmas party last year? The uncle giving me shit about “breaking the rules” couldn’t tell me the origin of this so-called rule.
Still wearing those jeans. Today. “You gotta match your belt to your shoes, bro.” News flash – I don’t wear belts that match my shoes. And I’ve watched enough guys cower when I loudly break that rule in front of them to know it drives them nuts.
So I invited them over for coffee and explained why it’s just fine to not match your belt to your shoes. Then I bought them matching belts and shoes as a “just in case” backup. Guys know I’m right when they see how handsome I look rocking nothing but mismatches all day.
When it comes to style, we obsess over rules instead of the underlying principles they’re based on. If I had a dollar for every time someone asked me about wearing boxers with shorts or bracelets with suits, I’d be able to afford that_checks_hand_to_head It’s like we think style has some set of regulations and laws that must be memorized. Let’s take suits, for instance.
Men have been humoring unlimited suit “rules” since folks started wearing suits. Never undo the bottom button. Leave a quarter inch of shirt cuff exposed at the sleeve.
Don’t wear a tie that’s broader than your lapel. Stop me – if I wanted to talk suits rules, I could keep writing all day. Turns out, some of these “rules” have legitimate bases in actual principles of menswear.
Things like fit, proportion, and yes – even color coordination. But others are completely made up, or at the very least, so outdated that they should be thrown out with the tuna sandwich you left in your desk drawer in college. The good news?
There’s an easy way to tell the difference. See this beautiful navy blazer I’m wearing? One of the rules of jackets with pleats is to never button your shirt’s bottom button.
Why? Because it allows your suit jacket to lay properly when you sit down or move around. Smart rule.
It’s about fit and functionality. Same thing with the part of your shirt sleeve that peeks out from your jacket sleeve. Again, it’s not about following a rule just to blindly follow it.
It helps define your arm’s proportions when worn correctly. Same rules apply if you’re wearing a dress shirt with jeans. Now see this yellow tee I’m wearing?
Goes with everything. Ignore rules that don’t make sense. Don’t like guys wearing sandals with jeans?
Too bad Gucci’s doing it, and they’re not taking “soccer moms” anytime soon. When I first started covering menswear, I tried to follow ALL the rules. Way too many, if you asked my wife.
You Might Also Like
To me it was inspiring how much I didn’t know about dressing well. It took me years of attending trade shows and fashion presentations to realize that every guy wearing something crazy was offended when I asked if they “understood the rules.” They understood the rules just fine. Better than most, actually.
And they were breaking them with impunity. Every trendy billionaire rapper hoop shooter in Yeezys popping up in your Instagram feed? Breaking the rules.
That internationally acclaimed fashion designer sporting sweatpants with a blazer? Breaking the rules. TLDR: Stop worrying so much about the rules and start paying attention to the guys who don’t follow them… but should.
Moral of the story: learn the rules so you know which ones actually matter. Those are the “rules” you should never break: Fit. Period.
If your suit doesn’t fit you’re automatically cheating yourself on looking and feeling your best. Same goes for a shirt, pair of pants, or a damn bed sheet. Nothing else comes close to overriding a poor fit.
Know your context. This isn’t about some made-up edict that ties must beankerchief style if they’re made of linen. It’s about wearing a suit to a streetwear showcase or denim shorts to a wedding.
Learn the difference between fun and foolhardy. Invest in timeless pieces that you’ll actually wear. Sure, I could buy another trendy Tee put out by a rapper because Twill Bro will probably wear it.
But I won’t because chances are, that Tee won’t fit me next season when StringBuilder Winter ends and you can actually wear quarter-zips again. Invest in things that suit your lifestyle. Always.
That being said, let’s obliterate a few rules: “Pleats are cheating.” Remember when pleats weren’t cool? Me neither. They’re making a comeback.
Just wait until suits with pleats become acceptable again. All of a sudden those anti-pleat guys will be crying into their UFO trousers. “No black with brown.” Bold color combos work, even black and brown. See: Best dressed guy at dinner party I threw last week. “Prints don’t mix.” Sure they can, if you pay attention to scale and color harmony. “You can’t wear socks with sandals.” Only if you’re visiting your dad at his retirement home in Florida.
Don’t sweat the small stuff. There will always be debates about what’s acceptable in style and what isn’t. And honestly, who cares??
Sounds like drama to me. There are no hard-and-fast rules in style. It’s not math.
You can’t screw up by wearing velcro sandals with your casual Friday khakis… but you probably should. I recently wrote about how I interview dozens of stylish men every year, ranging from folks who consistently land on Best-Dressed lists to stylish men who’ve cultivated admirable signature styles we covet. Not one of them thinks about dressing well as a rule-following contest.
They know the rules. They understand why those rules exist. But instead of blindly following them, they use that knowledge as guiding principles when getting dressed.
And that’s where most guys fail. They don’t know enough about what makes us think someone is well-dressed (FIT, appropriateness to occasion, grooming) to form their own opinions on everything else. That means the rules that say: “No belts with suits!” Isn’t true.
Ever seen me wear a suit with a belt? Bueller? Bueller?
Yeah, I’m breaking that rule as we speak. But I know WHY some people hate seeing a belt with a suit, too. “Wear slippery satin ties with dress shirts and top knots.” Also aren’t true! Whoever started this nonsense should wear socks with sandals for all I care.
Look, it’s 2024.
We don’t need to relearn old “rules” that no longer apply. In fact, I encourage you to break them – on purpose.
Throw on a pair of black jeans with a brown belt today. See how handsome you look in those shoes that don’t “match” your outfit. Notice how freeing it feels to stop caring about every little “style crime” you think you’re committing.
Trust me – I know guys with the worst fashion crimes – I work in fashion! Yet they’ve got it together when it comes to style because they stopped worrying about things that don’t matter and focus on the rules that do: Fit. Know your context.
Invest in classics. You’ll be fine. Maybe even start bending the rules a little yourself.
