Local Urban Gentleman: Jason Simon

We’re starting 2010 off on a high note, with one of the most stately Local Urban Gentlemen to date. He looks more like a Nordstrom men’s model than a student/lecturer… but I guess that’s the true making of an Urban Gentleman– innate versatility. Jason Simon is the first Urban Gentleman to exclusively represent New York, but he’s not just representing the state; he’s representing Brooklyn in particular, a place where more than half of its inhabitants seem to have a fetish for good taste and style. Jason not only offers us his above the bar elegance through his choice of words and style, but provides urban gentlemen around the world with quality examples on how to dress in the winter.
The Urban Gentleman is very proud to present, Jason Simon

Button Collar Oxford Shirt, Belt, Down Vest, Shoes: Polo RL / Polo Sport
Jeans: Earnest Sewn; Denim Jacket: Diesel; Silk Knit Tie: J Crew;
Tie Bar: Vintage Swank, Duffel Bag: David King Boston; Beads: H&M
Name: Jason Simon
Age: 24
Location: Brooklyn, NY
Occupation: Grad Student/Adjunct Lecturer
Style Icons: Gianni Agnelli, Sean Connery circa ‘James Bond’, Michael Caine circa ‘Alfie’, Harry Belafonte, Sidney Poitier, Malcolm X, JFK
Favorite Quote: “There is no better than adversity. Every defeat, every heartbreak, every loss, contains its own seed, its own lesson on how to improve your performance the next time.”- Malcolm X
Favorite Brands: Know what designer/ brands work for your style and body type and stick with them: Earnest Sewn, Ralph Lauren, Scotch & Soda, Cole Haan
Favorite Store: Century 21
Favorite Piece of clothing: Blue Bengal L/S Shirt
Bow tie or tie: When in doubt! Four in hand knot.
Flat front or pleated: Flat
Shades, hat, or scarf: Shades!
Ultimate goal: To have increased autonomy to contribute my energies and resources in places that warrant them most.
Favorite Books: Blink! M. Gladwell, The Apology of Plato Aristotle, Black is The New White P. Mooney
Hobbies: Traveling, Reading Periodicals, Thrift Stores,
Grooming product of choice: Andis T-Liner
Blazer, Khakis: Polo RL; Pocket Square: Robert Talbott
Hat: Weatherproof; Vest; Silk Knit Tie: J Crew; Gloves: Fownes; Duffel Bag: David King Boston
1. How would you describe your style?

Classic, functional, and above all, appropriate for my environments and activities.

2. How did you become so stylish?
Style is inward-driven. My style develops as I discover more about myself. I pull from what other folks are doing but my style begins and ends with me.

Beanie, Quilted Jacket, Shirt, Boots: Polo Ralph Lauren
Silk Knit Tie: RL Black Label; Gloves: Vintage Daniel Hayes
Jeans: Earnest Sewn; Duffel Bag: David King Boston

3. What advice would you give someone trying to find their personal style?

To thine own self be true. Forget trends, express yourself through what you wear, be appropriate for your spacings, function over fashion, and most of all, BE COMFORTABLE!


4.
What’s the best clothing advice you ever received?
“The world is bigger than timberland boots”

The story behind the quote:

I was 19 going on 20 years old at the time I was in SoHo window shopping. I went into a few local boutiques like Union NYC (their store will show you how I was style wise at the time) because I was looking for a Leroy Jenkins floral hoodie. By chance and boredom I wandered into a small shoe store, a very non descriptive place. I saw that it sold footwear, but the pieces were too trendy/avant-garde for my taste. They had alot of pointed toe boots with different insignia’s and designs (very Mark Nason-esque). A little italian guy sized me up and down (i.e. for those who step into high end stores as consumers sales associates are taught to look at your feet first.) I’ll never forget [what he said], I can quote his exact words til this day, “The world is bigger than Timberland boots”. It was not rude, he was trying to be helpful (I was wearing a pair of beeswax 6-inch premium boots at the time). I replied “I know” and promptly left the store, but that comment resonated with me more so at the time because I had 4 different colors of size 13 Timberland, and those were only the ones good enough to be in the rotation.

Blazer: Scotch & Soda, White Dress Shirt: Ike Behar, Hat: Weatherproof
Shoes: Frye, Jeans: Earnest Sewn; Pocket Square, Socks: Robert Talbott
Tie, Belt: Polo RL Blue Label

(a small letter of appreciation from Jason to the Urban Gent editors)

Dear [Urban Gentleman],
Your advice helped a pal of mine buy his first bespoke suit in Hong Kong. He is a heavy set guy; he played as a college linebacker for the past four years, is about the graduate in May, and wanted to step away from LRG for his life as a professional. The tips you posted guided him to a sound choice insofar as cut, detail i.e. double vented and color.

- Jason
Jason in Hong Kong. He just returned to the USA not too long ago.
Trench: Club Monaco; Shirt: Scotch & Soda;
Tie, Belt, Pants: Polo Ralph Lauren
What’s the esteemed Urban Gentleman manifesto/decree: “The Urban Gentleman is the modern gentleman, he is a man of style, class, culture…” In order to sufficiently become a cultured gentleman, one must travel when the opportunity avails itself. For the readers who are still students, please take advantage of the Study Abroad programs at your school. Explore the many countries in South/Central America, Africa, and Asia– indulge in their bountiful culture, try to learn their language. Take summer internships overseas if possible… if you are American go over to Europe perhaps London, Paris, or Milan if possible and vice versa. Don’t bankrupt yourself traveling, but seek programs that will extricate most of the costs.

Get a piece of Jason’s look:

Are you the next Local Urban Gentleman?
Answer the questions above and submit them to
urbangentblog @ gmail.com
along with 4 or more stylish pictures.
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6 Comments


  1. Wow. Is all I can say, great post.

  2. Dude is straightup Ivy Leauging it. This is how I plan to dress when I get to college.

  3. The polo boots go hard, definitely getting those. The question is though… how can I wear them in the Spring?

    -Llyod

  4. Quite the scholastic dresser I see

    What I like most about his looks are is bags, he doesnt over do it

    I feel there is a need for a guy to have a bag these days because of all of our digital stuff

    but no real man wants to carry a "murse" or anything that resembles a woman's purse

    he however have bags that are functional yet simpl

  5. This guy's confidence and style are awesome. He's putting a fresh spin on traditional looks. That's the key about fashion- adding your individualism and finding a good fit for you. Wear the clothes- don't let the clothes wear you! :)

  6. SkippyPeanutButterinDC

    Perfectly executed. He's amazing!

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