The Sartorial Dealmaker: How to Dress for After-Hours Client Meetings

Meeting clients outside of office hours is a valuable opportunity. Without boardrooms and office social mores, there’s a unique chance to connect and gain a deeper understanding of who your client is and what makes them tick. A fuller picture of the person you’re meeting is an invaluable tool for strategizing when you’re back inside the office doors. But then there’s the dilemma of how to dress for these social situations. Your presentation shouldn’t betray you as anything other than a well-rounded professional, while still nodding to the fact that your setting is more casual than the office. That said, your newest pair of Roots joggers might come off as a little too familiar. When the rules are in-between, it’s smarter to come up with a list of hard no’s than to pin down ephemeral trend advice. With that in mind, here are 3 pointers for what not to wear to after-hours client meetings!

Patio Lovers, Lose Your Shades… At First


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Though a well-crafted pair of sunglasses does do volumes for the vibe of your outfit, (not to mention the status symbol that a shiny new pair of Chanel shades convey) it is important to make eye contact when in conversation with someone who you want to make feel valued. Even if it’s just for the first leg of your meeting, it counts. Consider it the 2017 version of a gentleman taking his hat off when he enters a room. It’s polite, earnest, and makes your initial connection feel that much deeper.

Steer Clear of Embellishments

Ripped Jeans

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Loud patterns, slinky materials, and ripped denim are the enemy of business meetings as a general rule of thumb. Unless your client is Anna Wintour, stick to what you know will be well received by keeping things low key. Even though trends like ripped jeans are in for men and women alike this season, they’re too casual to convey professionalism. I don’t think quality denim is completely out of the question if the setting is right, but stick to a solid dark wash that’s neat and intact. Apply this slightly more conservative angle to anything you’re going to wear that’s on the funkier side – leather jackets, athletic footwear, etc. When in doubt about an element of your outfit, ask yourself if it’s neutral enough to not steal the thunder from your reason for meeting. You want to have the person you’re meeting with remember your conversation, not your outrageous outfit.

Don’t Wear Exactly What you Wore to the Office

Office garb

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Even if the client didn’t see you in the office that day, don’t wear what you had on in the office to your after-work meeting. If it’s formal enough for you to wear to your day job, there’s a certain familiarity that you miss the opportunity to establish with your client if you don’t let your guard down a little. (This is more a feeling you want to inspire than something you want to actually do, by the way.) Spark that authentic connection by losing formalities like your tie, a suit jacket, or a button down. The opportunity to present yourself in a different light, sans work garb, is one you should seize.

This quick list of what not to wear can act as lines for you to color within, leaving lots of space to infuse your outfit with splashes of your personality. They’ll stop erring too far on the side of casual, or too close to daytime corporate. Switch out of our office wear, keep your look simple and subtle, and be sure to not hide behind your accessories! What are your secrets for deciding how to dress for client meetings?

The Sartorial Dealmaker is a series devoted to business fashion and etiquette. In this monthly feature, we’ll offer style advice for business professionals, both men and women, as well as tips on business etiquette to help you make the right impression. Ever wondered how to look good and keep your cool when it’s 98 degrees in the shade, what to wear for an evening out with clients after work, or which wine to order for the table? The Sartorial Dealmaker has got you covered.

Nicole Edwards

Nicole Edwards is a fashion and lifestyle writer based in Toronto. She has worked as Associate Publisher of Private Islands magazine and Lifestyle Editor of Style Empire, and has contributed to NOW Magazine.