Last week I walked past our little regional library downtown Columbus while I was on my lunch break. The central office for the local library system is in this beautiful old building with stone stairs leading up to the front doors and black-and-white checkerboard floors in the lobby. It made me think of this email I got recently from a reader named David in London.

He’s about to start a new job at an accounting firm, and he was freaking out over what to wear. He’d driven by the office building earlier in the week and couldn’t tell what was appropriate based on what people were wearing. Some guys in full suits, some guys with trousers that looked like hiking trousers and blazers, someone in shorts (FOR FINANCE??? ), David just stood there worrying his dad was going to die if he walked into work dressed like that.

Teachers! When David was growing up, office workers wore suits and ties every day.

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Teachers wear ties no more.

Times have changed. This sprung me into reflection about how crazy office dress codes have become post-pandemic across the country. For as long as I’ve been teaching, it feels like we’ve been fighting the dress code battle.

Jessica teaches at a dental office where they’re still required to dress business professional daily (their uniform is scrubs, but the fitted style kind). I work in education and have spent years trying to understand what “business casual” even means when some teachers come to work in what’s basically workout gear and our principal wears Target khakis. But business casual is not consistent even within my school.

One of our vice principals has rocked the whole dad-core wardrobe vibe and never feels like he’s overly dressed, but also never looks sloppily dressed. So how does he do it on a teacher’s salary? I asked him, and I’m sharing his advice here.

When this whole “dress for your day” concept started blowing up a few years ago, I was working at a job where we wore khakis and polo shirts every day. I remember thinking how insane it was that people get to decide how professionally they need to dress each day rather than wearing the same thing every day like I did. Shouldn’t everyone have to wear a tie to do a desk job?

Well, now I get it. Because of the variations across industries – and even within industries – let alone individual offices/settings, I’ve started thinking more about how to dress for success on a budget no matter where you work. David ended up figuring it out and on his first day at the new job, no one died and everyone survived wearing clothes.

He learned that the firm dresses typically in suits when meeting with clients, but wears suit separates (meaning nice trousers, nice button-up, maybe a blazer) for typical office days. His strategy was to make sure he had staples in his wardrobe that could mix-and-match so he didn’t have to own eight full suits just to have options. This, by the way, is incredible for shopping on a budget.

Instead of buying a $400 suit that only works as a full outfit, buy a pair of navy dress trousers, a pair of charcoal dress trousers, a navy blazer, and three solid button-ups. Now you have over a dozen outfit options and none of them suck. I’ve preached this methodology for years because anytime you’re limited in what you CAN buy, you have to think more about how to mix-and-match pieces.

Law is similar – still pretty conservative but loosening up. My college buddy who works at a firm in Cincinnati says he and most of the other lawyers there rarely wear ties anymore except for court appearances and very high-stakes meetings with clients. The older generation of partners come into the office rocking ties daily, but the younger attorneys tend to stick with blazer-and-dress-shirt mostly.

Again, read your environment. Here’s the cool thing I’m seeing as this whole “dress for your day” thing has taken over. People actually dress for what they’re doing that day.

Not how professionally they need to dress every day. One day I need to wear a blazer because I’m meeting with parents and our principal. Another day I’m wearing a button-up and chinos, but I’ve got gym clothes under that because I’m doing labs with my kids and won’t feel bad getting sunscreen on my shirt.

It makes so much more sense to tailor your outfit to your day than to have weird rules about Mondays and Wednesdays being casual days. Businesses in the tech industry seem to have settled on just being neat and put together, but not overly formal. Dark jeans or slacks, nice casual button-ups, tidy trainers.

My wife’s cousin works for a software company in Austin and says as long as you don’t look homeless or disgusting, you’re probably good to go. “Don’t look like you just rolled out of bed” seems like a decent bar for most offices. Obviously marketing, design, creative-type jobs have gone ultra casual. But that comes with some pressure too.

When there’s no dress code, you have to look effortlessly stylish and put together, and that can be more challenging than just following a dress code. At least with business casual, you kind of know where the bar is set. But if your dress code is “dress to express your personal style,” well… you better have your style together.

Public service jobs (teachers and government employees) are still pretty traditional. After all, you’re representing taxpayers with their money so it only makes sense you dress like you take it seriously. My teacher friend that switched careers and now works in our state education department still dresses much more formally than she did teaching.

She went from full suit daily to business casual with the ability to dress up for meetings with school districts or state legislators. My theory is, fit and quality are more important than they’ve ever been. In the old days when everyone wore suits and dress shirts and khakis every day, you could sort of get away with buying cheap clothing that didn’t quite fit you perfectly because everyone sort of looked the same.

But now that there is so much variability in how people dress, the junky-looking clothes stand out. People notice when your trousers are too big or too small, when your shirt has that bubbly stain from the clearance bin at the petrol station. (Trust me, that happens way more often than you think.) Luckily for the budget-conscious, this means you don’t have to spend a lot of money. You just have to buy things that fit well and look “purposeful.” That $30 pair of chinos from Target will look 10x better than that $100 dress trousers if you get them hemmed to the correct length.

That $15 tailoring fee is the best money you’ll spend on clothing, I promise. Same thing with shoes. Slip on a pair of beat-up trainers with your nice jeans or dress a sloppy pair of $200 dress shoes and you ruin your entire outfit.

But you don’t need $300 dress shoes. A solid leather shoe from somewhere like Cole Haan on sale will work, or clean white trainers if your office is cool with that. Shoes make such a huge difference in an outfit, and they’re usually the first thing people notice when they look at you.

So what’s my recommendation for figuring all of this mess out?

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Dress slightly more formal than you think you need to, then adjust based on what you see when you get there. It’s almost impossible to dress down if you’re already dressed up, but super easy to go from business casual to wearing a suit.

Keep a blazer at work for days when it might be required. Invest in good staples that you can mix-and-match to create multiple outfits. If you’re still not sure what to wear, ASK somebody.

Most people would rather you ask them what’s appropriate than show up under-or-over-dressed every day. Not gonna lie, I’m actually kind of happy the pandemic ruined workplace dress codes for good. I hated having to wear a tie every single day to teach high school students.

But I also liked knowing what was expected when I went to work. So I think we’re finding a happy medium where it matters what you do and who you’re working with that day, but not to the point that we’re stressed out and taking clothing too seriously. And if there’s one thing I’ve learned shopping for professional clothing on a teacher’s salary, it’s that we can always use more options.

Author carl

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