Why I finally cracked the code on business casual after years of closet breakdowns

Okay, can we talk about “business casual” for a hot minute? Because honestly, it might be the most passive-aggressive dress code ever invented. It’s like your manager saying “just be yourself, but professional” which… what does that even mean? I swear every time I get an event invite that says “business casual attire,” I stand in my closet for twenty minutes having what can only be described as a minor existential crisis.

This happened to me just last month, actually. I was invited to speak on a panel about sustainable fashion – which, you know, should’ve been exciting except the dress code was the dreaded “business casual.” I tried on literally everything I owned. My friend Sarah got approximately fifteen mirror selfies from me, and her response to one particularly tragic blazer-and-khakis combo was just “Riley. No. You look like you’re about to try to sell me insurance.” Brutal but fair.

Here’s what I realized after that fashion meltdown: I was thinking about business casual all wrong. Instead of seeing it as this impossible puzzle where you can’t be too formal OR too casual (because apparently there’s some magical sweet spot that nobody explains), I started thinking of it as… well, kind of like a creative challenge. Bear with me here.

The outfit I finally wore – this vintage pinstripe vest I found thrifting, worn as a top with some dark wide-leg jeans and these pointed leather mules I splurged on last year – got three separate people asking where I got my “amazing suit alternative.” And I’m like, it’s literally a thrifted vest and jeans, but somehow it worked? The whole thing felt polished enough for the conference but still felt like me, not like I was wearing some corporate costume.

That got me obsessing over this whole business casual thing (occupational hazard of being an environmental consultant – we love analyzing systems that don’t make sense). I started asking everyone I know who actually looks good in work clothes how they do it. My friend Lena, who’s a creative director and somehow always looks like she stepped out of a magazine, told me something that totally changed my perspective.

“It’s not about finding the perfect business casual pieces,” she said, while wearing this incredible combination of a structured ball gown skirt with a vintage tee and blazer that should NOT have worked but absolutely did. “It’s about understanding that you need tension in your outfit. One piece that’s clearly business, one piece that’s obviously casual, and something in between that ties it together.”

This blew my mind because it’s the opposite of what most of us do, right? We try to find pieces that are sort of business-y and sort of casual and end up with these beige, forgettable outfits that make us feel invisible. But what if instead of aiming for the middle, you deliberately pull from both ends of the spectrum?

So I started experimenting. That vest situation I mentioned? The vest is obviously business, the jeans are clearly casual, and the pointed shoes split the difference. I’ve been playing with this formula ever since, and it’s honestly been kind of revelatory.

Like, I’ll wear this leather vest I thrifted (business element) with a midi skirt (somewhere in the middle) and these chunky sneakers (casual element). Or a crisp button-down (business) with wide-leg linen pants that technically have a drawstring but look tailored (casual) and some substantial vintage jewelry (the bridge element). Every time I wear these combinations, I get compliments, but more importantly, I actually enjoy getting dressed for work.

My colleague Marcus, who works in architecture and always looks effortlessly cool, does this thing where he wears oversized oxford shirts – like, properly oversized, not fitted – with these wool trousers that look tailored but are actually drawstring pants. Then he adds these architectural glasses or a really beautiful watch. The shirt reads professional, the comfort pants are secretly casual, and the accessories pull it all together.

I’ve been adapting this approach with pieces I actually want to wear. Yesterday I wore a white button-down (but oversized and with the sleeves rolled up), those linen drawstring pants I mentioned, and this chunky vintage necklace my mom gave me. Comfortable, professional, but still felt like my style instead of some generic office uniform.

The thing is, this approach requires you to break some of those unspoken rules that keep most work wardrobes firmly in boring territory. Like, who decided that “business” pieces can only be blazers and pencil skirts? A vest can be business. A structured dress can be business. A perfectly pressed button-down is definitely business, even if you’re wearing it in an unexpected way.

Same with the casual elements – it doesn’t have to be jeans. Relaxed silhouettes count. Comfortable shoes count. Anything with personality that wouldn’t appear in a corporate stock photo counts. The key is being intentional about the contrast instead of trying to split the difference with everything.

I’ve also noticed that the people who do business casual really well pay serious attention to fit. Like, obsessive attention. My friend Theo, who’s an editor and always looks incredibly polished, told me he gets almost everything tailored, even his “casual” pieces. “A perfectly fitted t-shirt looks more professional than an ill-fitting blazer,” he said, and honestly, he’s not wrong.

This has been a game-changer for me because I used to think tailoring was just for fancy suits. But getting my jeans hemmed properly, having my thrifted button-downs taken in at the sides, making sure my blazers actually fit my shoulders – it makes such a difference. Everything looks intentional instead of like I grabbed whatever was clean.

The other thing I’ve learned is that accessories can totally make or break the whole thing. Not in a “statement necklace makes everything professional” way, but in a “this shows I thought about my outfit holistically” way. Good shoes, a beautiful bag, interesting eyeglasses, quality jewelry – whatever fits your style, but it needs to feel considered.

I’ve been having fun with this lately. Like, I’ll wear a simple sweater and trousers – which could be boring – but I’ll add these chunky silver earrings I got from a local artist and suddenly it’s an outfit with a point of view. Or I’ll take that shirt dress approach where you wear a dress unbuttoned over jeans and a tank top, but I’ll add a really good belt that pulls it all together.

What’s funny is that once you start thinking about business casual this way, you realize there’s actually tons of room for creativity. You’re not trying to disappear into some bland middle ground – you’re playing with the relationship between different levels of formality. It’s like… fashion problem-solving, which appeals to the part of my brain that likes figuring out complex environmental systems.

I’ve been wearing a lot more vests lately because they’re such an easy way to add structure to casual pieces. This black knit vest over a white tee and wide-leg khakis with loafers? Looks put-together but feels comfortable. A pinstripe vest over a vintage band tee with a midi skirt? The contrast between the structured vest and the lived-in tee is exactly the kind of tension that makes an outfit interesting.

The sustainability angle makes this even better because you’re not trying to buy specific “work clothes” – you’re learning to use pieces you actually like in new combinations. I wear my weekend clothes to work now, just styled differently. That vintage tee that I love? It works under a blazer or vest. Those comfortable pants I bought for running errands? They look intentional with the right shoes and top.

I think part of why business casual feels so impossible is that we’re not really taught to think about clothes as a visual language. But that’s essentially what this is – you’re communicating “I understand the professional context AND I have personal style” through what you wear. The people who do this well aren’t following some secret rulebook; they’re just fluent in the language.

Last week I wore this grey cashmere sweater (thrifted, obviously) with slouchy black trousers and these chunky leather loafers, plus some architectural silver jewelry. Super simple, incredibly comfortable, but the proportions and the jewelry made it feel considered rather than just thrown together. Got compliments from both my boss and the barista at my coffee shop, which feels like the business casual sweet spot.

The most liberating thing about figuring this out? I actually enjoy getting dressed for work now. Instead of standing in my closet feeling defeated by the impossibility of business casual, I get to play with combinations and express my style within professional constraints. It’s creative problem-solving with clothes, which honestly never occurred to me before.

And here’s what’s really interesting – I think I’m perceived as more competent now, not less. There’s research showing that people who dress appropriately but distinctively are rated higher on both competence AND creativity compared to those bland, forgettable approximations of professional attire. Makes sense when you think about it – thoughtful self-expression suggests you can think creatively about other problems too.

I’m not saying show up to your corporate job dressed like you’re going to Coachella. But I am saying that aiming for the most forgettable version of business casual might actually be riskier than thoughtfully incorporating elements of your personal style. People remember you better, and in a good way.

So next time you’re having a business casual crisis, try this: pick one thing you own that’s clearly professional. Find one casual piece that makes you feel good. Add something that bridges the gap between them. Make sure it all fits properly. Then wear it with the confidence of someone who understood the assignment but completed it on their own terms.

Trust me, it’s so much better than standing in your closet at 7 AM wondering why anyone thought “business casual” was a helpful description of anything.