I've frequently been told that, in a business setting, to always be the best dressed person by one degree. If the situation calls for jeans and a t-shirt, throw a blazer or sports jacket over the shirt. If the situation calls for slacks or a collared shirt, make the slight upgrade to a suit or skirt.
No advice has ever agitated me more.
Here's the thing: There's a difference between dressing up and dressing well. Dressing up is wearing formal attire: think suits and ties, and dresses and skirts. Dressing well is being deliberate about styles, quality and fit.
While both have the same objective of looking good, the advice of always being slightly overdressed confuses the two. You can wear a collared shirt and tie and still look sloppy.
Also, there's something dreary about being in a room full of dressed up men and women in collars and shoulder pads; everyone looked exactly the same, like the marching zombies in the famous 1984 Apple Macintosh commercial.
Sure, in the short-term dressing up signals a sense of success and importance. Everyone wants to be taken seriously upon first-impression. But in the long-term, you compromise something more important: you.
What you wear is, in my opinion, the most immediate way to express who you are and what you stand for: a profound and inescapable human impulse.
Every day, you are afforded the choice to stamp your identity and personality--a reflection of your unique complexity as a human being--with an arrangement of fabrics. It's expressed through a unique combination of colors, materials and size variations.
When you dress up, you're forfeiting that expression; blindly subscribing to someone else's version of you. You're not only unoriginal, you're invisible.
When you dress well, you're meeting the standards of professionalism--communicating that your value in a business relationship is credible--while also maintining your identity.