While at a hip Portland restaurant eating breakfast with friends the other weekend, a bus boy in his twenties came up to one of the men at our table and said "That's a sweet shirt, dude." This is a real compliment if you are still in your teens or twenties. However, if you are in the man's world now, receiving a compliment like this is your wake up call that you are not dressing appropriately for your age.
A majority of men who work in industries that don't require a set dress code (i.e. wear whatever) fall into the "cool dude abyss." Their style hasn't changed regardless of their change in life status: career, title, position. They continue to buy and dress as if they are still in college or their early twenties. What may be hip and stylish for college boys (worn/distressed jeans and a graphic t-shirt), is not hip and stylish on a "grown" man in the workplace or when going out. Nor will dressing this way make you appear younger in a positive way. The never grow up ideal didn't do anything good for Michael Jackson's image.
Your assignment: take a look in the mirror and if you are in your thirties or beyond and wearing a graphic T-shirt to work or to go out on the town (see the example above from Threadless.com), you are probably mired in the abyss. The only exception is if you are a male fashionisto who has mastered the edgy, urban, street look (usually by spending thousands of dollars on designer clothes just to look like you just rolled out of bed).
How seriously do you take a college boy wearing a beer t-shirt? Just because you are older, wiser and have a nice title or position, doesn't necessarily mean people will take you any more seriously if you are dressed in "cool dude" attire. While you may get a laugh or two from the ladies when wearing your "LoveRobot" T-shirt, please remember they are essentially laughing at you. The message your never grow up attire sends to any woman of substance is "Never mind."
Dressing the part for you age and position will give you significantly more self confidence (even if you don't think you need any more). And the best part is the return on your effort; your peers, colleagues and superiors take more notice and express more confidence in you. When the CEO stops you to say "that's a sweet shirt" and you look down and see a quality, tailored fit dress shirt, polo, etc.; you have shed the dude and become a man.
-Lisa Bruckner Certified Trunk Club Consultant

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