Setting Your Personal Style Agenda

An OTC reader recently sent me something of a social science question about dressing well.  He asked, essentially, does it matter what you wear when no one is looking?

Though he does travel to meet with clients and check in at the home office, this gentleman has the enviable ability to work from home.  However, by his own admission his daily professional wardrobe has settled to an uncomfortably ratty level of old shorts, tee shirts and a trusty baseball cap.

While I fully concede that working remotely has enormous benefits – I occasionally telecommute myself – hewing to the perpetual college boy thing can eventually have a negative psychological impact on personal presentation. Call it the frat effect.

“Sure, I’ll don a suit when I’m at a meeting, but what more must I do?”

That way of thinking completely misses the point. While I tend to critique the more formal side of men’s clothing, a suit is by no means the only “dress up” thing in a man’s wardrobe.

Too often, guys see dressing well as a chore, something to avoid, or something against which to fight. Maybe, as I once said, it’s a latent fear of dandyism. More often, it is a misguided sense of self righteousness; a feeling that you’re fighting conformity, not buying in – you know, being more real.

Of course, very often those folks are just arguing their own sense of conformity: “if you’re getting all dressed up than you’re just a suit, a drone.” Well, get over it.

There is a world of style and personality between flip flops and a three piece suit. Just to be clear, I am not talking about when you roll out of bed and make that long trek down the hall to check the e-mail. Wear a thong if that makes you happy.

But when you step out of the house or log onto a video conference I believe you enter a sort of social contract. What you have on now matters. Once you start interacting with other people you ought to show them the same level social and sartorial respect you yourself would expect in return. You should make an effort to dress well because you want to.

That said, I firmly believe in always be comfortable and true to yourself, in your own skin or in you own clothing. But whether you like it or not, people judge you by how you dress, how you carry yourself and treat others, your social skills, how you speak, etc. Within eight seconds their mind is made about what kind of person you are and it can take years to alter that perception. How you react to this universal, and highly researched, truth is your choice.

If you want to (or have to) wear a suit every day than take the time to learn what makes a great suit great and what cut and fit works on you. If you wear business casual all the time, make the effort to expand your wardrobe. Instead of polos and khakis five days a week, buy some nice tailored pants and dressier shirts. Sport coats and odd jackets are a fantastic way to dress up your look without really dressing up.

And make sure to have everything properly tailored.  When your clothes fit they have a totally different feeling – that’s when you start wanting to pick out an actual outfit in the morning.  Equally important is being open to learning about yourself and what kinds of clothes work with you.

For example, I was recently down in Palm Beach for a meeting at The Breakers and stopped by the Ralph Lauren store located right in that fantastic hotel.  As I chatted with the store’s manager, Patrick, he pointed out that I was probably a 44 short when it came to suit jackets and sport coats, like he is.  This was news to me; as far as I was concerned, I have always been a 44 regular.

However, as he explained, in most cases the short is simply shorter in jacket’s body, that’s all.  For someone like me, or Patrick, who is middle of the road when it comes to body type,  a short often provides a more tailored and proportional fit.  I tried on a lovely gabardine blazer and sure enough, the fit was far more proportional and darn if he wasn’t spot on.

I kept my mind open and was willing to accept that I’m always learning, and in the process I learned something new and valauable.  Thanks Patrick – teaching is one of the most important aspects of good retail.

And just like that you can start to assemble a more flexible and professional wardrobe.

If you work from home and have client or co-worker meetings less often, than keep abreast of general style trends. Update your wardrobe selectively and make sure to have someone else give you an honest assessment about color, fit and style. Pay attention to how you look when others aren’t around so that when they are, you always present your best face.

What do you think? Tell me your thoughts on this discussion or stories on dressing for the real world.

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  1. Adam Nelson

    Chris – Great commentary. I think your blog helps to bridge that gap between work and play.

  2. Bill

    And dress up a little when you go out to eat. I am so tired of seeing younger people where the woman has on a nice top and skirt and the wreck she is with hasn’t combed his hair and has on a tattered tee shirt and basketball shorts with flip flops. Have some pride!!

  3. My dress says either how I am feeling about myself or how I want my day to go. I can don a cashmere robe over pjs to complement a lazy morning at home with newspaper, or slip on penny loafers, a print tee and khakis to water the lawn. Later, I might throw on a linen jacket and complete the look for Brunch. I can also have those days where I am not sure and I look it.

  4. I like the idea of “always dress as if your ex-girlfriend was going to be the next person to see you.” Make everyone around you know that you’re prosperous and successful by the way you dress and that will carry over into your psyche – making you prosperous and successful!

  5. Great comments everyone – I especially like Jamie’s rule about dressing for your ex-girlfriend. A friend of mine actually had that happen at an event where he ran into his ex-wife and her parents! He looked great, was incredibly polite and nonchalant and heard later that he was the topic of discussion afterwords – much to his ex’s irritation.

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