Esquire Magazine’s Best Dressed Real Man Contest 2010…The Journey


If you had a chance to check out the About section of this site you will see that I was one of 5 finalists for Esquire Best Dressed Real Man in America 2010. There were thousands of people who entered and over eight long months the field was narrow down to the final five. The 5 finalist were actually featured in the Sept. 2010 issue of Esquire Magazine (on page 54 I believe) which featured a brief profile on all of us.

I followed the contest for a few years, however; I would not have known about the contest if it wasn’t for my fraternity brother Steven Penn Markoe that told me about it in 2008 when Kenyatte Nelson won the prize. In 2009, I decided that I was not ready to enter the contest but really gave it a push for 2010 and obviously you know the rest.

The outcome of the contest in September was that I did not win the contest overall, however; I was named the fan favorite for the contest and a few other bloggers (and people of the United States and abroad) did really dig my style. Since the contest usually opens up around February of every year I decided to show the looks that got me to the finals and into Esquire Magazine this past September.

Fan Favorite from

There was a fair amount of mystery during this contest, especially in finding out if you won a particular portion. The day that I won the fan favorite title, I was surfing Facebook and had a message written on my wall from another contestant (and eventually a finalist) Wale Oyejide congratulating me on winning the Fan Favorite Title. When getting this news, not only was I excited, I did a few celebratory jumps in my office then went back to work.

From June until August I got to ride the wave of holding the only guaranteed spot in the finals and on August 11th the September issue of Esquire Magazine was release with the rest of the top 5 Best Dressed Men in America (Congrats to grand prize winner Angel Ramos of Miami Florida) being revealed.

When looking back at the looks that I entered, I believe the overall reason I made it as far as I did was because I had a lot of variety in my looks. As my style has evolved over the years I’ve always said you have to actually wear the things that you own. Having the clothes and knowing what to do with them are two different things that some people don’t seem to understand.

Keys to my wardrobe:

  • Know the versatility of a piece of clothing
  • Never buy outfits
  • Do not rush to buy something because you think you need it.
  • Get a tailor that you can trust to do your alterations
  • Know the basic style rules and then twist them to fit your personal style

Here are all the looks that I entered in the contest for Esquire’s Best Dress Man 2010


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Categories: Men's Style, Style Tip, Versatility

Author:Sabir M. Peele

Founder & Creative Director of menswear style & lifestyle blog Sabir serves as an independent brand consulting working with brands like GQ, AskMen, Indochino & Z Zegna (among others). Selected as #GQFall Best Dressed in 2013 & one of Esquire Magazine Best Dressed Real Men in America in 2010. Follow @MensStylePro on Instagram/Facebook/Twitter. Email with your inquiries.

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5 Comments on “Esquire Magazine’s Best Dressed Real Man Contest 2010…The Journey”

  1. January 13, 2011 at 10:56 PM #

    Very interesting! Thanks for putting this together, and congrats again!

    • January 13, 2011 at 10:58 PM #

      Thanks Andrew. I am a huge fan of of your site and the advice you give.

  2. January 25, 2011 at 8:40 PM #

    Wow, this is so cool! I can see why you were a finalist, I really like your style. So many guys these days our age don’t know the value of dressing to impress. It’s really a lost art!

    • January 25, 2011 at 8:42 PM #

      Hi Maggie,

      Thanks for reading and for the shout out to my style. I feel like if you can walk out the door each day and put your best foot forward to how you look it will translate to your work as well.




  1. Fashion Express Tie Plaid - January 18, 2011

    […] Esquire Magazine's Best Dressed Real Man Contest 2010…The Journey … Cotton Blazer by Old Navy | Waist Coat by Heritage | Denim by Gap | Khaki colored shirt by H&M | Knit Tie by Unknown. Sweater by H&M | Striped Khaki pants by Express | Oxfords by Zota. Bowtie by Andrew's Ties | Plaid Shirt by H&M . […]

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