Dapper Gent of the Week: Jonathan Cole  

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Hello “Cigar Community” and “Cigar Family!” Thank you for joining us and reading another great article here at Red Lips and Cigar Sticks™ we are happy to have you as one of our new, and/or faithful readers!

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Today’s dapper gentleman (Dapper Gent) of the week is Jonathan Cole out of Chicago, IL.


There are some great qualities and characteristic of men within the “Cigar Community,” who mixes fashion with their cigar lifestyle.  It displays empowerment when a well-dressed gentleman has a great eye for fashion, as well as a profound appreciation for cigars. One’s fashion choice is based on his personality and level of comfort to be causal, and/or dapper.

Therefore, our “Dapper Gent” of the week, Jonathan Cole, his fashion sense started at a very early age. He was directly influenced by his father, who had a great sense of style. Jonathan’s father would put thought and effort into everything he wore. And, he would make ascertain that his sons followed suit and looked their best for every occasion.


Once Johnathan became a teenager, ​he really started to develop his own sense-of-style. Even as a teen, who wore uniforms to school, he was very meticulous about his attire. He made it his point, to pick out the best quality shirts and slacks, and he always creased and pressed his clothing the night before school. These very early habits influenced Jonathan to subscribe to fashion magazines, which he would use these as a resource and a guide to assisting him with putting together different looks and ideas, at the time.

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​​And, from there, this motivated and inspirited Jonathan to pursue his passion for fashion, which has put him in the company of other business professionals in the fashion industry. Also, as he advanced in his career and from the course of meeting other individuals, he became a fashion consultant, which he has his very own business/brand page (stayrandomlyfly), and YouTube channel (RandomlyFly).

📸: @ron_mac_photography

In addition, Jonathan was introduced to cigars roughly two years ago, by a good friend, who works at a cigar lounge. The Avo Classic is his cigar of choice because it’s not too strong and it has a smooth pull. Jonathan is a novice to the “Cigar Culture,” so he hasn’t developed his palate, per se, so he likes to stick with a mild cigar.

📸: @thevintographer

Jonathan’s drink of choice when having a cigar is Dusse Cognac.

Photo Credit: D’USSÉ

Jonathan is our Dapper Gent of the week for his vigilant spirit and his tenacity, as well as charisma to follow his dreams and incorporate those very core values that he learned from his father to persevere.


You can find out more about this Dapper Gent on his IG page:


Author: Naimah “Ni” Pears


Welcome, I’ am Naimah “Ni” Pears! I always wanted to have a platform to share some of my creativity, as well as my enjoyment for writing, loving cigars, bourbon, and whiskey, and way too many other cool things to name all here.  However, I hope you will continue to visit Red Lips and Cigar Sticks, the magazine, to learn more about me and the Cigar Lifestyle. I’ am not an expert, but I am extremely knowledgeable!

Also, please connect with me on the listed social media sites from the homepage for a more personable connection and subscribe to the magazine, to stay updated and current on the latest articles.

Thanks for visiting and I hope you’ve become inspired. Peace and Love! Ni

Gents and Cigar Sticks is the affiliated name for the men’s section of Red Lips and Cigar Sticks. There will be a weekly featured “Dapper Gent”, to showcase his style, cigar preference, his drink of choice, and any extracurricular activities to highlight about him will be included. If you are interested and would like to be featured, please send your name, location, a description about of your style (optional), and 5-10 clear, unfiltered pictures of yourself, the pictures can be a collage, to redlipsandcigarsticks@gmail.com, and/or send a direct message via IG @redlipsandcigarstixx

Disclaimer: Images submitted will be featured on Facebook, Instagram, Twitter, or any of our social media platforms. Please be advised: once published, the article and pictures will not be removed or taken down. Thank you in advance!

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