The Stylish Progression From Boy To Man

I believe there comes a time in every young man's life- in which he must answer the pinnacle question: "Am I ready to be a man?"

When answering this he must consciously think about his past — and what the future could possibly bring. He must ask himself "Am I sincerely ready to travel and be on my own like those before me– (insert names of great men that inspire you, fictional or real)". Ready to tell mom and dad, "It's okay, I can handle it." Ready to face it when he has to cut out Friday nights at Stats or Pink Pony because the insurance on the brand new Audi just isn't going to pay for itself.

And just as he asks himself these questions about life's essentials, he must also ask himself the same about another "life category" that actually, even if not admittedly, is as important. Just as there is a time in which his actions must ripen from boyish to manly– as must his style develop from the worlds to his own. It is quite hard to know when that time has come. The decision to buy a house, buy a car, or even to get married comes more naturally to most men, than to decide that "I must now own my look, my own style."

The truth is, most men never own up or develop it. They progress from immaturity to dignified maturation while always missing one element that few are able to acquaint themselves with. Many become great men, distinguished, erudite men, but not quite embodying the maximum meaning of those words because he lacks the complete essence of it.

Those before you who took the important leap did so because they felt it necessary to grow into manhood– at it's entirety. It is a complex situation– to decide what style, what look, will sum you up. To figure out what people will see of you before you mutter the simplest word. As you walk through Whole Foods, figuring out where they stash the Bolthouse smoothies– what one second summary will the girl restocking the oranges think? As the red double decker full of tourist pass you while you're off 42nd and 6th– what will be their impression of the true new yorker as they gaze upon you?

And as I ask, you must ask– travel deep into the depths of who you are and decide. Do you wish to present an outward image that fully reflects your personality? Or do you wish to be true to yourself while yet knowing that providing those on the outside with a particular reflection will only enhance your current position– be it financial, emotional, or simply artificial (in the many ways it can be)? The choice is yours…

It requires reflection, perhaps a long overdue visit to the men who have come before you– fathers, grandfathers, great uncles. Maybe it takes you finally releasing what will make "her" like you and focusing on what will make "you" like you… while hoping she sticks around for the progression.

For some, this journey, this leap, this step happens naturally– happening between 24-30 (lucky bastards). While for others, because of life's circumstances, late 30s, 40s, and midlife crisis's will induce a band-aid pull effect– this change will be sudden, very quick and fast. But for you, because you were smart enough to be on this particular site and read this particular article on this day, you have the delighted and highly coveted– choice.

You can choose to further peruse in a stagnated manhood, silently chuckle because you semi-arrogantly but mainly pridefully have already become a man and developed your own style, or you can begin this journey. Flip the coin, roll the dice, choose from the petals of a flower if you wish… I suggest that maybe, just maybe it is time to become an, Urban Gentleman.

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23 Comments


  1. That was just deep. You should really send that to GQ or somebody. You really need to have your column in somebodies magazine. Or start your own. If urban gent became a magazine I would buy it.

    I am 23 and I use to go with the trends and the baggy clothes. But now I work in the professional arena. Reading this blog really has helped me to turn my fashion life around and find a style that works for me and that I feel comfortable with.

    So really thank you.

    On another note. When did you create the urban gentleman II?

  2. Wow, that was the best article I've read in awhile. Seriously, I totally feel you. I'm 26 and just last year I had to make "that decision" and what's so funny about it is that I actually did talk with my uncle about. I'm trying to be partner in my advertising firm by 29/30 and I knew I had to project that image. I love this blog and I understand that you may not be able to update it every single day, but know that I'm always going to check and support the urban gentleman.

  3. Antonio, I agree! This should be in Men's Vogue ASAP. If you don't submit it, I will on your behalf.

  4. That was great. There is a lot of really good advice to take to heart. Thanks for sharing that with us.

  5. AsianPersuaison.

    Samuel- ditto. Couldnt said it any better. great Read!

  6. Impressive

    This is the BEST article I've read since the "How to be a Man" in Esquire… submit this Cindy- they'd be crazy not to print it.

  7. yeah, what they said, lol. two thumbs up

  8. "Or do you wish to be true to yourself while yet knowing that providing those on the outside with a particular reflection will only enhance your current position"

    deep, thanks for this.

    -L.A

  9. Same as everyone else- Great.

  10. The Urban Gentleman

    Thank Everyone!!!! I'd love to have a little section in a major mens mag… maybe one day soon:)

  11. The Urban Gentleman

    Oh and Antonio– I've had the other Urban Gentleman for about a month now… I had some other post before then, but the first real article I created for it is the one above.

  12. I am still trying to figure out what shoes Ne-Yo was wearing at the awards (it seems you had the same question)!
    Anyone know! My brothers birthday is next week and he needs a pair, ASAP!

    Beautiful site. I will be sending thi discovery to all my friends!

    Please let me know!
    AlannaElyce@gmail.com

  13. This is excellent. People form Costa Rica reading this and like it. Thank you

  14. Inspiring!

  15. Jerrell Trulove

    yo, great article, great poster (i own it) people need to read this.

    Jerrell

  16. Every blk man should read. It a real eye opener!
    Durin frm Detroit

  17. This article was perfect for me today! I just made a new post today about retiring from hip-hoppper/hipster look. This article really spoke to me. Thank you Urban Gentleman. I can’t wait to see what the future holds for this company

  18. I will talk about it to my friends. Thanks ;)

  19. I’m so happy that I stumbled onto this article. I am 20 yrs old and I am at that moment trying to get a balance in my wardrobe do I stick to my jeans and sneaker combination or my plaid pants and brogues. Reading this article has just helped me in making up my mind, first impressions count! I want people to see a man and not a boy.

  20. Where can I get a copy of this picture?

  21. Nice site. I am glad I came across it.

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