Ask Harry: How to Dress Business Casual
Let’s break down this classic workplace dress code and how to make it work for you.
By: Harry Rosen Staff
Let's be honest — "business casual" has more than a few interpretations and might just be the most misunderstood dress code, at work or outside.
The issue is, “business casual” is vague, open to interpretation, and varies wildly from one company culture to another.
But instead of stressing over whether your outfit is "too casual" or "not formal enough," let’s simplify things.
At its core, business casual is about striking a balance: looking polished without going full-on formal. Think smart meets relaxed, with just the right touch of professionalism. It's meant to be versatile — an outfit that works in a morning meeting and still feels comfortable grabbing coffee afterward.
The easiest way to get business casual right? In one word: contrast. Pair one structured or elevated item with a more laid-back piece to keep the outfit grounded and intentional.
For example:
- Start with tailored trousers — they bring structure and a sense of formality
- Add a knitted polo in place of a button-up
- Layer on a casual overshirt or unconstructed sport jacket
- Slip into some sleek leather sneakers instead of dress shoes
The result? An ensemble that feels modern and professional, without looking stiff or overdone.
Still not sure what we mean? We asked a few friends to help us break it down.
Business casual means something different to everyone — so here are three ways to wear it, each tailored to a different starting point.
Edward already has the business casual formula down — a button-up, cotton chinos, and a solid sweater — so, we gave him an office-appropriate refresh that made things more interesting.
We traded his chinos for flecked wool trousers, sneakers for suede Chelsea boots, and his sweater for a mauve cashmere quarter zip — the anchor of this look. The bones are the same, but the slightly more elevated items make all the difference.
Nathan is excited about his first office job, but less so about navigating the dress code. The solution? Introduce elevated versions of pieces he already gravitates toward.
We knew Nathan would find comfort in a soft cable knit sweater and light wash jeans, while his black dress shoes offer a kick of polish and suede overshirt a hefty dose of luxury, yet not without the comfort of his favourite flannel.
Polished, presentable, and without straying too far from his casual, off-duty style. Now that's how to look (and feel) like a million bucks.
Paul is a veteran when it comes to dressing “business casual,” in fact, enough to know that the definition can change over the years. Without straying too far from his sartorial roots, we’ve put Paul in something a little more modern to help him keep up with the times.
Our solution? A contemporary take on suit separates. We’ve swapped his classic suit-and-shirt look for a dressed-down sport jacket paired with relaxed drawstring trousers and some sleek leather sneakers.
Current, considered, and yet, entirely his own. Contemporary C-suite style, done right.
At the end of the day, we’re firm believers in bringing things back to the basics — and when it comes to business casual, it’s all about the two Ps: purpose and personality.
Business casual isn’t about playing it safe; it’s about expressing your personal style while respecting the purpose of the environment you’re in.
Everyone's workplace dress code and personal style is different. When in doubt, remember: confidence, comfort, and just enough cool will take you far.
With a little intention and creativity, you can make business casual work for you — not the other way around. Ready to upgrade your business casual wardrobe? with a Style Advisor in-store or online today.
Have a men’s style question? Reach out to us on Instagram @harryroseninc and we’ll answer it next time.