Last week I ran into this guy Dave I used to work with. Dude looked like he lost a wager with his wardrobe. He had on this nice polo style shirt and what appeared to be a blazer on top. But from the waist down… gym shorts and dad sneakers. And I mean big dad sneakers. The kind you know are specifically engineered for maximum cushioning during extended shopping trips.
He explained to me that he’s been doing work calls from home like this for three years now. Blazer and dress shirt look sharp on camera, pants and shoes who cares. Mind blown.
Here’s the thing, offices are opening back up and nobody knows what to wear anymore. I’ve gotten texts from friends asking, “Patrick, do I still own jeans that aren’t workout jeans?” and “Patrick is it bad that I forgot how to wear a belt that matches my shoes?” My neighbor asked me if khakis were still cool because he hasn’t worn his since before the pandemic and now wasn’t sure they counted.
We’ve all completely forgotten how to dress like acceptable humans from the waist down. Business casual wasn’t easy before we all mastered the fine art of looking halfway decent from our nipples up and whatever from our ankles down.
Business casual has never made any sense to me. Business? Casual? What does that even mean?! Business-ish but not really casual? Casual but not too casual? Professional but not stuffy? Whoever came up with that dress code wasn’t much help. Before COVID you’d walk into an office and see people rocking the grief counselor style all the way to dudes who probably shouldn’t be allowed anywhere near an office building.
But now everyone’s gone wild. Last month I had meetings at a few different offices. Same building, same freaking day – sweatpants wearing dude sitting next to guy in a full on suit. Girl in blazer with stylish shoe dressed shoulder to shoulder with another woman in jeans and high-dollar sneakers. Nobody knows what to wear because it turns out there are no hard rules!
What’s a dad supposed to do now? I reached out to HR departments, managers, and executives to see what actual employees should wear these days. The answer I got from everyone? It depends.
Ugh. Wonderful. But hear me out. The most helpful tip I heard was to "dress for your day." Kind of flies makes sense if you think about it. If you’re not going anywhere and you’re just sitting in your office doing calls all day, then heck, dress how you want. Throw on a nice shirt with jeans and be comfortable. But if you have to meet with people or clients, maybe don a pair of pants that aren’t fleece.
This then creates a whole new problem. What if you have to mix and match through the day? Commence panic. My friend Alex works at an advertising agency and showed me his office wardrobe essentials. "Business shirt for morning Zoom calls, nice jeans for lunch meeting with the team, suit for afternoon client presentation." He said. "I basically need a second wardrobe at work because you never know what kind of day you’ll have."
Trying to stock multiple outfits at work is exhausting. Remember when you could just throw on khakis and a button up and you were done? Now we have to think about it! Carry extra clothes at the office in case we need to look halfway professional later.
Ok but for real though, here’s what I’ve learned works if you want to fit in anywhere these days. Especially for guys. Jeans are pretty acceptable now but you have to have good jeans. Dark washed, properly fitted jeans. No tiny rips or weird saggy-looking jeans that just make you look like you lost a fight with your pants. Toss on a nice shirt and you’re good. Maybe a blazer too if you want to look extra fancy. Sneakers are getting pretty accepted too but I’m talking crisp, simple sneakers. Not Halloween costume sneakers or skateboarding sneakers.
There’s a balance you have to strike now. Call it the seesaw rule. If you’re dressing down in one area, you have to dress up elsewhere. Comfortable shoes? Make sure your shirt isn’t wrinkled. Jeans? Wear a nice shirt and maybe throw on a jacket.
A friend of mine who works at a financial services company said it best, “Don’t wear anything you’d wear to cut the grass or go out nightclubbing. Used to be that was the rule and you were good. Now there’s this huge grey area in the middle and nobody knows.”
We are living in the grey area my friends. Sneakers with business clothes used to be a big no-no. But they’re becoming more accepted as normal. But there is a difference between expensive sneakers and the ones you wear to walk your dog. The stakes are higher than they used to be when you’re getting dressed.
What I’m seeing more than people wearing the wrong style of clothing are people not caring for their clothing. Shirts with stains you can see from across the room, pants that are practically wrinkled into permanent folds, shoes that looked like they’ve been through the apocalypse. When was the last time you washed your pants!? Didn’t everyone forget because we were trapped inside for so long with no one to see us?
I talked to an executive assistant who says she now keeps stain remover in every conference room because so many people are showing up to meetings with food stains from their kids. You know who else has food stains from their kids? Me. We all do, which is why I’m not admitting that out loud.
Body shapes have changed over the last few years for so many people too but everyone’s still trying to wear their pre-pandemic pants. There’s nothing worse than seeing someone try to squeeze into pants that don’t fit anymore. Or shirts that are hanging off of them. Get those things tailored friends, do it for your wrists!
The biggest tip I can give anybody is to <a href="https://sartorialhim.com/the-art-of-the-side-hustle-wardrobe-dressing-for-multiple-roles/">buy clothes that can go multiple ways</a>. A solid dark colored blazer goes with literally anything from dress pants to dark colored jeans. Clean white sneakers are great for just about any office situation while keeping your feet comfortable. Button ups are your friend. Get a few that fit really well in different colors and fabrics and you can build outfits off of them.
And please for the love of jeans that fit – make sure everything fits you. Not the you before kids. Not the you when you start that exercise routine you’ve been saying you’d do. Fit your clothes to your current body that you have now.
I honestly love that we can finally dress how we want to work. But man, it comes with a lot more thought than just grabbing your khakis. You actually have to think about what you’re wearing now.
I think we will start to see factions of offices based on clothing style. The traditional business guys, the remain comfy crowd that has mastered Business Athleisure, the fashionistas using the office as their own personal runway, and the lost souls texting people to ask if their shirt is too nice for a 2PM meeting.
And Dave? He told me he has real pants and dress shoes at the office. Pants-too-small-shirts pop into the bathroom before big meetings then change back into shorts and gym shirt when he’s done. “It’s tiring,” he said. “I kinda miss having a uniform.”
I didn’t tell him that in another ten years we’ll probably all be required to wear suits again. Clothing cycles like that. But until them I’ll do my best to fit in and stay stylish while my children tear up everything in my closet.
