The saddest place to shop for clothes isn’t Avenue Z midnight drunkwear or Costco’s camo activewear section. It’s the men’s workwear department of your local department store. Those ugly lighting grids goddammit.
Rows and rows of boxy navy suits that might as well be oven mitts, stiff white shirts that have never known the taste of pocket protectors or ale, and dry-clean-only neck accessories that aspire to be known as “ties.” It’s torture. One grey Simon Flexcore suit feels like the narrator in A Christmas Story trying on leg lamps for size. But I was there recently, wandering the sad wasteland that is Macy’s menswear department, when I witnessed a dude being sold maybe the worst advice of all time.
Business casual patrician grey hair hiding behind a counter, lecturing a young guy who was picking out his first professional gig garments on how IMPORTANT IT WAS TO “KEEP IT SAFE.” The kid was shopping for interviews, and this man told him he “didn’t want him to stand out too much” and that “we typically recommend something simple, something basic.” If you’re reading this and thinking, Well duh Tim, don’t wear a clown suit to your job interview, congratulations – you get to wear watches with cow spots on them to work. I’m talking about subtle variations within the professional dress code.
Ways to distinguish yourself from the white shirt prison gang while still dressing like an adult who shows up for work on time.
I wanted to grab this kid by his Twitter-ready Red Sox fleece and set him straight. To explain that dressing well for work doesn’t mean sacrificing personality or becoming a granite-skinned android. It means mastering the nuances of menswear fundamentals so you can inject something – anything – to differentiate yourself within strict dress codes.
So I bit my tongue and left the store promptly. But not before jotting down notes on my phone for what would eventually become this article: a guide for dudes who work in offices or have boring dress codes who still want to express some semblance of individuality through their clothing choices. Because let me tell you something about the highest-performing professionals I’ve ever met while covering business, finance, and men’s style: the guy whose office looks like a Dockers warehouse sale is not always the guy who’s rising fastest up the ladder.
Instead, it’s the people who understand the unwritten rules of office dress codes so well that they’re able to subtly bend them in ways that establish clear visual identities. I’m not saying show up to your next board meeting wearing shank shade eyewear or a velour blazer. I’m saying there are degrees to “business professional” and even the most conservative workplaces generally have looser standards than you think – they’ll just often penalize self-expression that doesn’t respect the tacit rules of the office dress code. “Most dress codes are designed to create a baseline rather than a ceiling,” Richard Wu, a banker turned menswear entrepreneur, recently told me. “They don’t say ‘you can only wear a solid colour shirt,’” he explains, “they say, ‘at the very least, you should wear a button-up shirt.’” I’ve interviewed my fair share of executives, investors, and CEOs over the last decade and a half of working in menswear media.
And something that many of the most stylish – and successful – have in common is that they understand the difference between having a dress code and wearing a uniform. Rather than hiding their personalities in bland cotton sacks they call “business attire,” they use texture, fabric, proportion, and fit to express something about themselves without distracting from their work. Here’s how they do it.
The worst thing you can do when shopping for work clothes is to approach pieces like they’re finished products rather than building blocks. Because that’s not how they’re designed to be worn! A button-up shirt, blazer, and pair of slacks were not created to homogenize people into one large blur of office norms.
They were created as a framework to be personalized, adjusted, and built upon. You know the pieces I’m talking about. The ones you think you’ve already nailed by default because you’ve worn them before.
The problem is, most men approach them as if they’ve already peaked in terms of interest and personality because you just…haven’t. Take the goddamn navy suit. We could all stand to pay a little more attention to our navy suits.
Sure, in its purest form – flat wool, medium-fit jacket, plain white button-up, plain pair of dress shoes – it is exceedingly boring. But that’s because it has been worn and re-worn to absolute death. Stop wearing a navy suit that feels like it was fitted by Mike Brady.
Look for details that read as “grey suit” from across the conference table but something slightly more exciting when you lean in for that Power Point presentation. Maybe that means a subtle texture to the fabric – nailhead, faint herringbone, hopsack, etc. Something that shifts and changes when it catches light as you move throughout your day but isn’t overwhelming.
Perhaps that means you pay more attention to shirt details than you currently do. Once upon a time, a solid white or blue broadcloth was your only safe default for shirts. But as long as you stick to subtle patterns and textures, most workplaces will be fine with you wearing an off-white twill instead of broadcloth, a microstripe or microdot pattern, or even a fun weave like oxford cloth or end-on-end. “There are so many opportunities to mix it up with texture,” Patrick Chen, design director at a menswear company known for its modern classics, told me when I asked him about professional dressing. “The first misconception with professional dressing is that it has to be boring and visual monotony.” Notice how he said “visual monotony” and not “uniformity?” There’s a big difference between dressing appropriately for work and dressing exactly the same as everyone else who works there.
Most workplaces have some form of a dress code. It’s how we respect the professional spaces we share with others. But just because your office expects you to look like a version of a suit and tie doesn’t mean every man in that office has to dress identically.
Remember when we talked about building blocks earlier? This is where that notion pays off. Look for variations on those classic pieces that are still undeniably professional but allow you to step just far enough outside of the box that you’re remembered after you leave the room.
That means reaching for a warm grey suit instead of navy or charcoal. Or sticking with white or light blue shirts but opting for an off-white, cream, or pale blue colour instead of stark white. Shopping for shoes?
Go with burgundy or dark brown instead of black. Sure, your coworkers will still see you coming a mile away, but you’ll be the one with the unexpected yet memorable wool overcoat rather than that dad jeans dad yelling about politics on Fox News. This has been a slogan I’ve lived by for years, especially when it comes to men I profile for work.
Learn their style secret and appreciate how they use traditional garments to establish presence rather than disappear at work. Take one of the most successful bankers I’ve ever met: Cameron Strang, former CEO of Vice Media and current CEO of Fortress Investment Group. A 100 percent suit-and-tie kind of guy, but known by everyone (including me) for the amazing pocket squares he always wears.
Outwardly, his style is traditionally professional. Navy and grey suits. White button-ups.
Conservative ties. The difference is in the details he personalizes: pocket squares. Vintage Liberty prints, hand-blocked cottons from India, textures you don’t find anymore.
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None of his pocket squares are flashy, but they are eye-catching and serve as his trademark. “A lot of times it’s the little things that you can do to stand out from the crowd,” Strang told me when I asked him about his strategy. Another example? His love for old English rep ties. “All of my ties are traditional patterns and colours,” he explained. “But the older ones tend to be made with a slightly heavier silk and have hand rolled edges.” It’s such a subtle effect that maybe one in ten people would notice, but to someone who knows and loves ties, it creates a subtle yet noticeable difference that speaks to Strang’s attention to quality.
That also describes how most people perceive clothing and dressing well. We *know* clothing affects how we’re treated and how productive we are at work – but do we really know how? According to a 2015 study published in Social Psychological and Personality Science, when we wear clothing we associate with qualities like competence and professionalism, we actually perform better on tests measuring abstract thought and negotiation skills.
But nowhere in that study does it say dressing well for work requires you wear clothing completely devoid of personality. OK, so you’ve upgraded your traditional work uniform staples. Now it’s time to flex those muscles on items that are typically more forgiving in professional settings.
Your neckwear is the perfect place to start. Yes, even traditional industries that enforce suit-and-tie dress codes are typically fine with you wearing what you want, as long as A) it’s a tie and B) it’s not wildly inappropriate for your office. Think: ancient madder prints, subtle paisleys, regimental stripes, small geometric patterns.
They all scream “I work in professional services!” without looking identical to your coworker’s ancient madder print. “A lot of times I equate people’s tie collections to their personalities,” David Grimes, who manages large finance projects at Accenture but dresses much more boldly than most in the biz, told me when we spoke about his approach to professional dressing. “If you had two consultants who worked at the same management consulting firm and wore exactly the same suits and exactly the same button-downs but different ties,” he continued, those ties can send totally different signals. Grimes has honed in on what he calls his power tie formula for work: traditional patterns, yes, but nontraditional colour combinations that frame his face and add visual interest without venturing into “Obi Wan Kenobi costume” territory. “I generally save my solid red power tie for client presentations and meetings,” he says. “But outside of that, I prefer tie combinations that are memorable but not loud – I really enjoy rich, regal colour combos like burgundy and gold, bottle green and silver, and navy and burnt orange.” Ok, so tie collections are the gateway drug to building out your professional wardrobe with personality. What else can you tweak to stand out from the crowd?
Accessories, my friends. Belts, watches, even your briefcase or portfolio can communicate subtle variations that tell people you’ve got some serious swagger. Not all of your personal touches have to be clothes!
Show someone your watch collection and they’ll instantly know if you’re an Apple Watch guy or a vintage Rolex kind of dude. Eyewear is another oft-forgotten opportunity to establish visual distinction while maintaining appropriateness. A great pair of dress glasses can elevate the whole ensemble, even if your shirts and blazers are entirely workplace conformist.
That extends to leather goods, too. A classic but interesting portfolio is another subtle way to stand out – if you make sure it actually stands out from everyone else’s Black ROOT-approved leather portfolio. Think of how you dress for work like the reverse of a mullet: business-up front, party in the back.
You know the parts I’m talking about. Little details that allow you to maintain a traditionally professional appearance but showcase your personality where only you might notice on a daily basis. That could look like wearing traditional suits with unique linings that are only visible when your jacket’s off, French cuff shirts with vintage cocktail cuffs links as your secret weapon, or just rocking some badass socks that no one sees unless you sit down.
The point is to have fun with the things no one else cares about or notices, because you know they’re there. An attorney I wrote about earlier this year for Quartz built his entire professional style philosophy around this concept. From a distance, Daniel Koh seems like every white shirt, button-up lawyer in New York City.
Until you get five feet away from him and notice his suits all have surgeon’s cuffs (button holes that are functional and not just for show, a traditional tailoring detail most people don’t notice). Or how his French cuff shirts always have vintage sterling silver cufflinks he’s picked up while travelling. Or how his pocket squares are cut from remnants of his children’s baby blankets, another detail that’s only visible when he pulls his jacket aside to reveal a white linen peeking out of his breast pocket. “They don’t impact how seriously clients take me or how effective I am in court,” he explained. “But when I feel fancy, it helps me be my best self.” And honestly?
Helping clients (and yourself) feel their best is why we dress for work in the first place. It’s even more crucial when you’re stuck in a business casual environment. Business casual is the worst.
Mostly because it usually ends up being somewhere between what you’d normally wear to work and what you’d wear to lounge around your flat. Nobody wants to dress like they’re headed to the office, but slouchy button downs and shit-ass khakis don’t actually feel that comfortable either. They just…look bad and feel way too casual. “The worst part of business casual is it created this purgatory of dress for men,” Chen said when I asked him about his least favourite dress code. “Business casual has eliminated the need to wear a jacket and tie, but most offices don’t realise it doesn’t mean you get to dress like you’re scrolling through Twitter.” The reality is that most business casual dress codes have something they’re trying to communicate, whether it’s comfort, approachability, modernity, or cost savings.
Figuring out the “why” can help you work within those confines while still establishing a strong visual identity. Which is exactly what I’ve seen some of the smarter business casual-dwelling folks do in industries that tend to skew business casual – especially tech-adjacent spaces. That usually means elevating what you’d otherwise wear to “uniform dressing” – picking one type of item that’s made incredibly well (better than your colleagues) and then wearing it all the time.
Think: the guy who only wears Sperry boat shoes but has them in every colour. Or nice denim and a collection of timeless, well-made turtlenecks that he rotates through. It looks intentional rather than sloppy (which, let’s be honest, most business casual dressing is) and helps establish a cohesive brand for yourself.
That’s the philosophy David Binetti, founder and CEO of healthcare tech company Grascoda, has taken with his work wardrobe. He wears some permutation of the exact same thing every day. “I like cotton chinos – the highest quality cotton I can find. But only button-down shirts and Alden suede loafers,” he says. “And if it’s cold out, I’ll throw a navy cashmere jumper on top.” It’s comfortably casual but far more impressive than the dude wearing Grizzlies sweatpants with the hoodie unbuttoned.
And for guys whose workplaces operate in that weird business professional-meets-creative space? Like ad agencies, design firms, media companies.
The challenge with these industries is you sometimes need to telegraph how creative and original you are without sacrificing the professional appearance that lets clients know you’ll charge them enough to pay your own bills. “I’ve always felt that creative folks that work for corporate businesses needed to have something a little different about their wardrobe,” James Torres, creative director at digital agency Collective Digital – who works with plenty of corporate financial institutions and healthcare clients himself – explained to me when I asked him about dressing for his job. “More specifically, something that wasn’t quite as conformist as everyone else’s but didn’t scream ‘look at me!’ either.” For Torres, that meant keeping things mostly traditional on the bottom (black or grey trousers, white or black shirts) but rotating through a collection of jackets with unique details that aren’t overpowering. “I can wear a black jacket and From Tokyo jumper and blend in with the bankers down the street,” he said. “But add one of those crazy jackets on and suddenly people know we’re a little different.” Funny how jackets can do that.
Ultimately, dressing well for work isn’t about rebellion. It’s not you vs. the dress code. It’s about you accepting the dress code, but stepping outside of it in small ways that let you develop your own presence while still dressing professionally.
The problem isn’t that workplaces want you to dress well or professionally. It’s that far too many dudes interpret those guidelines to mean “anything remotely interesting is grounds for firing.” When I saw that kid at Macy’s learning that timeless menswear tennant of “keep it simple stupid,” I wanted to scream. He didn’t need to know that dressing for work is conservative by nature.
He needed to know that there are always options, even within the most stringent of dress codes. Yes, you’ll have to make compromises based on your workplace. But instead of listening to old grandpas at department stores drill that into your head, learn how to work the system and use those dress codes to your advantage.
There are plenty of guys out there making clients notice at work without sacrificing personality. You just have to know where to look.
