When I was eight years old, my mum would prepare my outfit for school each night before bed. Navy slacks, white polo shirt, complete. With my private school uniform, there was no agonizing over whether one polo shirt was just acceptable to wear on top of my navy slacks.
Even on “free dress days,” uniforms simplified the decision-making process: no jeans, no graphic t-shirts, no trainers. As a kid, I loathed those restrictions. I tried (and failed) to convince my mum that letting me wear Spider- Man shirts and light-up tennis shoes was a basic freedom fight.
Fast-forward to age thirty-five and there are days I pine for that simplicity. I spent twelve minutes this morning staring into my closet because I couldn’t decide what to wear to a restaurant opening that described the dress code as “elevated casual.” Did that mean upscale jeans and a nice jumper?
Chinos and a sports coat?
Full suit, but try to look like you didn’t try too hard? The invite gave me zero hints aside from those two gems. Welcome to the anarchic world of 20twenty-four dress codes.
Gone are the days when restaurants said “no shirt, no shoes, no service.” Today’s dress codes are more often communications briefs issued by corporations that once made dressing for work as simple as owning a white button-down shirt. Businesses large and small have gleefully eradicated dress codes, replaced by frustrating euphemisms and nebulous guidelines that leave the interpreting to you, the consumer. Look, I get it.
This is partially about comfort. Casual work environments are nice. We live in a global society with a lot of diverse cultures – and one person’s casual attire can look totally different from someone else’s.
Clothing rules have long been dictated by white people with classist notions of professionalism. Does every person who wears a suit to work do so to maintain some outdated power structure? Of course not.
But relaxing dress codes across the country hasn’t solved these systemic problems – instead it’s caused a whole new set of dilemmas where unclear guidelines have become the new restrictive rules. Last year I started compiling a spreadsheet of all the silly little dress codes I’d see on wedding invites or event listings. Here are a few of my favourites: Whimsical dry (street) Creative comfortable formal Celebrate contemporary Beach formal Oh, how I love a good dress code ping-pong match.
My personal favourite from the list was creative comfortable formal, which was for a gallery opening in Brooklyn. No clue what it meant, but I went with dark jeans, a cashmere jumper, and a tweed jacket. Was I over dressed compared to some guests?
Yep. Under dressed according to others? Yep.
So I tell myself that means I hit the sweet spot. But this isn’t just happening at cocktail parties and weddings. The dress code death has swept through nearly every facet of American life.
Offices. Restaurants. Places of worship.
Broadway theatres. You name it. Covid helped speed up this trend.
Spend two years wearing sweatpants to “work” and suddenly Dress Codes With Capital Letters start to feel archaic. Remember when restaurants used to tell you to “come as you are but don’t wear jeans”? Last month I ate at a Michelin-starred restaurant in Chicago where the tasting menu cost approximately the same as a used Ford Focus.
There was a guy wearing a hoodie, shorts, and Crocs at the table next to mine. Coat and tie wouldn’t have cut it for that guy twenty years ago. The maître d’ didn’t care.
Or airplanes. My father travels for work at least once a month and he still dresses up to fly. I’m old enough to remember when airplanes weren’t glorified cattle-call resorts.
My dad wears slacks, a button-down shirt, and loafers. But pajama trousers are everywhere now. I’ve boarded aircraft in outfits I wouldn’t wear to walk my dog.
I should be celebrating this clothing freedom. Relaxing outdated standards is a good thing. More self-expression!
Less needless conformity. And fewer opportunities to enforce white supremacist or culturally-specific standards of professionalism. But instead too many unanswered questions from too few guidelines create uncertainty and insecurity.
In a post-dress code world, how do you know what’s appropriate? How do you not end up stuck-as-the-only-person-in-a-suit-while-everyone-else-is-in-jeans (or the reverse)? I hear this anxiety from my readers ALL THE TIME. “My wedding is ‘beach formal’… what the actual fuck does that mean?? ?” or “My new job has this really vague dress code of ‘dress how you feel comfortable’ but I don’t want to look out-of-place on my first day.” When you give people infinite freedom to choose how they dress, you’ve also given them infinite reasons to worry about that choice.
Researchers tested this theory at a grocery store by setting up a booth to sell jams. When researchers offered 24 varieties of jam, only 3% of people walking by ended up buying any jam. When they scaled that down to six varieties of jam, 30% of grocery shoppers made a purchase.
Simply put: too many choices stress people out. That’s what happened with business casual. Infinite choices + zero guidelines = max anxiety for American citizens.
I recently consulted with a tech company that was having this exact problem. They decided to empower employees by ditching the whole “business casual” dress code and just telling everyone to “dress appropriately.” Guess what? Nobody knew what appropriate meant.
Junior staff wasted precious cognitive energy each morning scrolling through their closets wondering if that hoodie was acceptable. Were jeans too casual? What about trainers?
More often than not, employees would end up mirroring what their senior leadership was wearing because some unstated hierarchy had been established based on attire. Which sort of defeated the entire purpose of getting rid of the business casual dress code in the first place. This lack of clarity has affected me too.
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Last spring I moderated a panel at a conference where the dress code was clearly marked “business casual.” Business casual used to mean something to most professionals – slacks, collared shirt, no tie necessary. I wore slacks and a button-down shirt. One panelist wore a suit and tie.
Another wore jeans and a polo. The third guy wore khakis and a quarter-zip jumper. Not one of us read the dress code wrong.
The dress code itself had become so meaningless that no one description could adequately fit its new parameters. So what’s a mildly-anxious Anglo man to do when every institution tells him how to dress but gives him zero instructions on how to actually do that? Well, I’ve developed a few coping mechanisms that seem to work pretty well: I pay more attention to the restaurant / venue / occasion / host than whatever contrived language is on the invite.
There’s a difference between a “casual” invite at a James Beard Award-winning restaurant and a “casual” get together at someone’s backyard BBQ. Tech “business casual” is much different than Law Firm Business Casual. If I’m in doubt about a dress code, I’ll ask people.
But not like, “Hey dude, what are you wearing?” I ask specific questions about ties and jeans and trainers. Those questions produce specific answers that actually help me. I do this all the damn time now.
Twice in one weekend last month. I’m an embarrassing amount consultative about these things with my buddies because EASILY OVERDRESSING beats stressing about what to wear any day of the week. Build a wardrobe that can be mixed-and-matched for different levels of formality.
I mentally organise my closet into tiers, with t-shirts and jeans on the low end and suits on the formal end. That way I can dial up or down within that tier based on what feels appropriate. That’s where having a lot of staple clothing pieces that can be mixed-and-matched really helps.
Give yourself some guidelines. If external guidelines don’t exist, create your own. I have certain steadfast rules that I almost never break: No shorts in the city unless it’s above 85 degrees.
No trainers with fitted clothing. No jeans during client meetings. Again, these rules aren’t universal laws that all humans should follow – these are just rules that help me feel my best in most work situations.
This last point is key. With the crumbling of Western civilization’s dress codes, how we choose to dress ourselves has become far more important. I don’t mean that in an “Instagram influencer” kinda way.
I mean in a “having your own standards and sticking to them” kinda way. The men and women who’ve adjusted to life after the dress code succeed not by trying to look like everyone else – but by having a clear set of standards for how they dress in different situations. One of my best friends, Thomas, wears some version of the same outfit to work every single day.
Black jeans, black or white t-shirt, black sport coat, white trainers. That’s it. Every day.
He works in advertising, so it’s surprisingly appropriate for almost all of his client meetings and in-office days. He rarely has to think about dress codes because he’s created his own through a loose uniform. Now, I’m not saying we all need to wear uniforms.
But if your clothing options suddenly feel endless (and therefore stressful), I encourage you to create some internal guidelines. Maybe that means you always wear a collar shirt for client meetings. Maybe it means you never wear trainers to church.
Maybe it means you’ll never wear “athleisure” to dinner at a restaurant. I don’t care what the standards are – it just helps to have them. Dress codes are disappearing, but that doesn’t mean we shouldn’t dress with care.
Dress codes used to make life way too restrictive for many people. But the complete abolishment of dress codes has been replaced by a freedom that many don’t know what to do with. There’s no shame in asking for help sorting all this out.
Talk to your boss. Talk to friends. Talk to me.
Hell, I’ll even give you a free phone consultation if you really get stuck. Above all, try to trust yourself. Almost no one is going to care as much about your outfit as you do.
If an event says casual but it’s at the International Shoe Museum, maybe casual doesn’t mean sweatpants. When in doubt, ask the host. “Hey, I’m so excited for your birthday dinner and want to dress appropriately – what did you have in mind when you said ‘festive attire?’” Most people will be happy to clarify. And please wear stuff that fits you well and that you feel good in.
I cannot tell you how many people ask me about wearing clothes that are too big or too baggy because they “feel comfortable.” Comfort is great, but there’s a reason baggy clothes don’t typically look good on people. Wear something you feel confident in that also fits well and is neatly pressed. That will get you far, far better than wondering if your bootcut jeans are “business casual” enough for the office.
Relax, have fun, and know that you’ll get it wrong sometimes. I’ll never forget showing up to a birthday party once where the dress code was “creative black tie.” I rocked up in a midnight blue velvet dinner jacket (complete with ostrich jacket buttons) only to find out my friends interpreted creative as “regular ol’ suits, but no tie required.” Lesson learned. I stood out.
Were people upset? Nope.
Did I care?
Not really. Back to that aforementioned “elevated casual” restaurant opening. What did I end up wearing?
Dark jeans, merino polo, unstructured navy blazer. Probably shouldn’t have gone with jeans. Probably should have asked the chef/host what he had in mind when he described the dress code as “elevated casual.” Who knows?
But here’s what I DO know. I felt good wearing what I wore. My outfit was appropriately clean and fitted.
And once I arrived, I didn’t think about my outfit once. Now that’s what I call dressin’ appropriate.
