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The conventional wisdom on dressing for success is ridiculously straightforward. Buy good, simple, quality suits and separates. Iron your shirt. Shine your shoes. Wear a good, understated watch. Splurge on a high quality handbag or tie. Avoid the outré and the trendy. Dress like your boss, or for the job you want to have.
To which I say: BOR-ing.
Instead, wear orange. Wear polka-dots. Wear both together!
I am a big advocate of orange and polka-dots because they do stand out, they are outré, and since I've worked from home since 2000, I really want to make a splash when I go into my office. I don't want to have to be reintroduced each time I walk into a meeting. I want someone to say, "Great to see you again, Erin. Nice dress!"
The classic, the understated, the quietly chic--they make an impression a little bit at a time, day after day. If you're only in the office one day a month, that impression takes years to settle in. Nobody says, "Oh, Erin, you remember her. She's the one with the fashionable, yet timeless, tank watch and the well-cut gray suit." No, they say, "You know Erin, she wore that dress with the giant yellow birds on it." Or "She's the one with the bright blue eyeglasses." You get the idea.
You may be thinking, shouldn't people know me for my work? Well, they might, but in any company over a dozen people, how many will really have seen your work? How many will have looked at it closely enough to judge it? And how does "You know Erin. She wrote that incredible Robertson piece" help them put a face to a name in a meeting?
When you work in an office every day, you have more avenues for presenting a fuller picture of yourself to your colleagues. You have daily opportunities for random conversation--not just the working lunches or the few minutes of chit-chat in the elevator telecommuters make do with. You can decorate your office or cubicle with your rubber-stamp art, your memorabilia from your college curling team, or pictures of your (adorable) Welsh corgi.
But if you're a telecommuter, all your colleagues really know about you is your work and your look. And since the colleagues who don't work directly with you will only know about your look, it's worthwhile to spend a little time thinking about what that look should be.
Your look is your brand
If you have a distinctive enough look, it can function as your own brand. People often cringe at the notion of "branding" themselves. But your personal brand doesn't have to be a focus-tested, genericized, rubberized simulacrum of a real person; it just has to be a concentrated version of you. When people talk about having a "personal brand," what they really mean is that people who are successful in business are usually also successful at being completely themselves. They don't hesitate to express what's important to them--their ideas, their vision, and yes, their style. Think Diana Vreeland, the fashion-magazine editor who wore kabuki-style makeup every day, or Matt Drudge in his hat, or Steve Jobs in his black turtleneck.
Finding the essence of you
If you've spent so long in Dockers purgatory that you're not sure exactly what you would have to wear to be a concentrated version of yourself, there are ways to figure it out. Grab some magazines and rip out every page where you like something, or visit a site like Style.com, which shows images of runway shows, and bookmark what you like.
If Style.com is too fashiony, try The Sartorialist, for pictures of real people on the street. Remember you're just looking for things that attract you, not committing to wearing any particular item. When you have a big stack, figure out what those images have in common. Is everything red? Retro? Narrow-cut? Vintage-inspired? Write that down. If you find you're attracted to several different types of look, do a rough count. Do severely modern looks outnumber the wispily romantic two to one? There's your answer.
When you do go shopping, start in your closet. Are there pieces of clothing you love, but have never worn to the office? If not, why not? If they're too casual, or too worn-out, make a note to look for more formal or newer versions. (I've had great luck finding new replacements for much-loved pieces of clothing on eBay.) If a favorite piece just doesn't seem "suitable" for the office, try it out somewhere else. Wear it out to dinner, or a concert, or just running errands, and see if it feels more natural after a test run or two. Maybe it's just that you always wore that bright purple sweater with jeans, and with a pencil skirt or dressy trousers it takes on a different (but still completely you) feel.
Once you're out of your closet, you can try shopping elsewhere. The only rule is that you must absolutely, positively refuse to buy anything that you don't love. If it doesn't make you feel like you'd want to have your picture taken in it, don't buy it. This may mean, at first, that you buy very little, but so be it; if you telecommute you can get away with fewer office clothes, anyway.
Differentiating details for men
Admittedly, it's harder for men to break out of the boring-suit-and-tie corral. (Although you can check out this blogger for some eye-popping inspiration.) But when everyone is in the same uniform, smaller changes can really stand out. It's possible to get every conceivable accessory, from fountain pens to cufflinks to suspenders, to, I am sure, portable oxygen tanks, emblazoned with the logo of your alma mater, or your favorite sports team, or even a distinctive pattern or solid color. Splurge on monogrammed shirts, distinctive eyeglasses and watches, or even fancy socks. Even one signature piece of jewelry, especially one with a good story behind it or a lot of personal significance for you, will help you differentiate yourself.
You can even make your hair work for you. I know a very successful investor with extremely long hair--which he needs for his other job in a rock band. Not only does it look cool, it also makes him instantly recognizable in a sea of blue Oxford shirts and khaki pants.
One final note for men and women alike: if you're going to start dressing like the most exuberant, most out-there, most-highly-concentrated version of yourself, you have to do it consistently, especially if you telecommute. You'll just confuse people if you're in a conservative suit one day and something really wild the next time you go to the office. It's fine to have varying levels of your look, from casual-Friday to Important Meeting, but they should all seem as if they came from the same closet, not like you had to run out and borrow two cups of business suit from your neighbor.
Later this week, I'm heading into the office. I plan to wear a bright green fan-printed dress with turquoise trim. I'm fairly confident that no one will say "I'm so sorry--what's your name, again?" Erin McKean lives in Chicago with more dictionaries and more dresses than anybody could ever really need.
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Reactions to "Dressed to Impress"

Erin is my inspiration to be me! Her blog, www.dressaday.com, makes every day a happy day.
Rita

There is a man on my bus ride home every day who has fashioned his hair into small devilish horns on the top of his head. To add to the effect are wild sideburns, but other than that he is very conservatively dressed. I have not checked but I fully expect that his incisors have been filed to a wolfish point.
Leslie
Senior Market Strategy, Garrigan Lyman

Awesome article! It is so nice to see something written about how I have felt for so long.
Heather Silva
Helmer Silva Interior Design

Great article and all right on. I worked in retail, on weekends for many years (a very long time ago) and the customers whose names I remember were the ones with some type of outstanding (consistent) signature to their appearance.
Good advice, Erin.
Stephanie

I consider Erin McKean rather a secret hero of mine, for her sunny outlook, her uncompromising love of language, and her very distinctive and non-officey sense of style. Is there a woman in a cheery duro? Does it by chance have orange rick-rack? Must be Erin!
I haven't had the courage to follow her example very thoroughly yet -- I'm only learning to sew, so I'm largely still stuck with what's for sale -- but I'm planning to follow her example in my own still-to-be-discovered way. Thanks, Erin!
Jo

This is an excellent thing to ponder and incorporate, especially for those of us who work at home but also do quite a bit of networking and need to make an impression fast. Also, nothing says you're successful at your title like looking the part, especially for a creative. Thanks!
Melissa Balmer
Principal, Conscious Creative Connecting
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