‘The Season of Style’: OSK Styles Owner Omar Kinnebrew Takes Calculated Risk In The Name Of Fashion

Kinnebrew talks finding your passion, how a man knows he has style and forgetting the safety net

After transitioning into adulthood, there are a few recurring themes I’ve noticed. 1.) Nobody has life fully figured out. 2.) It is never too late to make a transition that makes your life meaningful. 3.) Your passion can drive you to your paycheck. I recently got the chance to sit down with OSK Styles owner Omar Kinnebrew who only reiterated these points. OSK Styles is online destination for custom-crafted garments, hi-end shoes & leather goods.

A Hamden, Connecticut native– Kinnebrew found his true home down south at none other than North Carolina A&T; which he refers to as the best HBCU in the world. Amid playing football for two seasons and pledging Kappa Alpha Psi, Kinnebrew majored in Chemical Engineering and minored in Spanish. After realizing engineering was not his calling, he promptly changed his major to Business.

Working at a print communication company for a little over eight years, Kinnebrew was going nowhere fast with only one promotion in the meantime. Even after obtaining his MBA from Mercer University, Kinnebrew found himself at a crossroads. Everyone’s worst nightmare ended up becoming a blessing in disguise for Kinnebrew. The last one in the door and the first to go, he faced layoffs at a healthcare IT company that brought him to what we now know as OSK Styles. 


It All Started with A Pocket Square

Before he found himself at a crossroads, Kinnebrew put his engineering skills to work. Already in the world of custom pieces, Kinnebrew began searching for a way to keep his pocket squares from falling. Finally crafting a mechanism that worked, Kinnebrew started selling that along with other accessories on Etsy, eBay, Amazon Prime, local boutiques, and other platforms with relative success. “I knew if I put a little more effort into my brand, I could build up and grow the way I want too after looking at my initial revenue numbers,” says Kinnebrew.


With no background in fashion, it’s his passion that keeps him moving forward. “If the passion is there, I’ll work hard to make it work,” says Kinnebrew; a gem that resonated with me. Luckily with a background in business and many years of sales under his belt, Kinnebrew saw that he had a leg up. If you’re thinking about going into business for yourself, Kinnebrew forewarns that marketing & sales will comprise about 85 percent of your business.


Best Dressed Man In America

In the business of custom garment’s, you can imagine there is a target demographic in mind. For Kinnebrew and OSK Styles, his ideal consumer is a C-suite senior executive who falls within the range of 85K or more, between the ages of 38-56, in the metro Atlanta area or within a 35-mile radius.

A rather specific niche, thanks to social media Kinnebrew has a much broader audience that looks to him for custom pieces. Those seeking custom garments are looking for a few things; something for a special occasion such as a wedding, helping with redoing their wardrobe, or have seen his work and want to start purchasing custom pieces.

What does a man that creates custom garments for most women’s ideal man wear himself? While sitting with him, Kinnebrew gives me the rundown on his ensemble.

“This is very random, but I am wearing a double-breasted jacket a little lighter than forest green. My shirt is slate with a geometric pattern, with red thread and a French cuff” explains Kinnebrew as I notice his Batman cufflinks. He continues with “custom grey stretches denim jeans, double monk strap, dual-toned, mixed material, green kit suede and denim shoes— all custom made by me.”

The rundown didn’t end there, getting his start with men’s accessories it wouldn’t be complete until I knew what his wrist and hand candy consisted of. “Normally I would be wearing the watch my wife bought me for our one-year anniversary, but today I’m wearing a Japanese divers watch. My beads are from a fellow Nupe, LJ Soul Stones, and this is black sodalite, and the Jade beads came from Amazon. In my attempt to be a non-corporate badass I’m trying out random rings!”

One of the best-dressed men in America credits his fashion inspiration from various spaces and people. He doesn’t hesitate however to credit his father as one of his first guiding lights. The former UGA football player and one of the first black players on the team added his flair to his style back in the 1970s, especially for his larger body type.

“Two wide lapels, everything fit well, large bell bottom pants, taco meat out, the most fly people on Earth were probably rocking around in the ‘70s,” says Kinnebrew.

Outside of his immediate circle, Kinnebrew says he aims to be casual, while not putting in too much effort all while still looking stylish. The goal is to make whatever you’re wearing look cool. Like most of us with social media platforms, it’s common to pull inspiration from Instagram or Pinterest where up and coming models and photographers consistently put their most fashionable foot forward. Outside the norm, Kinnebrew credits interior design magazines as another form of inspiration when it comes to fashion. “Color, contrast, the pairing of tones, materials, and hues all work within the world of design whether it’s furniture or clothing.”


Season of Style

Have you ever intentionally waited for a specific season to roll around just, so you could style and profile? If I had to guess would it be Fall? Although not your typical thought or question, I asked Kinnebrew if he had a seasonal preference and after much thought, he could agree Fall is the season of ‘style.’ “Fall gives you more opportunity to succeed or fail with layering. It allows for the expression of particular style compared to warmer months especially for men who like to keep it simple” says Kinnebrew.

Atlanta summers only require a shirt, shorts, and shoes to make it through the day. But Kinnebrew notes that you can quickly see if someone has style no matter the season based on how they wear various things in different ways. “When it’s not too cold, we want people to tell us we look good, in the fall you get to show off different things,” says Kinnebrew.

This sentiment leads to me asking another question I’m sure a lot of men wonder themselves…how does he know if he has style? In my mind the answer was simple; ‘if you know, you know’—right? Kinnebrew suggests “the easiest way a man knows he has style or if he’s doing things right is to not by receiving compliments from women but other men.”

Not the answer you were expecting huh? The narcissist in us wants to be complemented by any and every one. But what is the logic behind being complimented by another man? “If you can get a guy to step out of his comfort zone, a lot of times men don’t complement each other. Although when we do it still has to sound as masculine as possible, it’s still genuine. If anyone goes out of their way to compliment you, you’re doing something right” says Kinnebrew.


In Every Man’s Closet, You Should Find

I couldn’t let Kinnebrew leave without first lending some style tips to the fellas looking to step their game up. I asked what staples every man in the working world should have in his closet, here is the rundown:

  • 1-2 full three-piece suits, minimum. Go for navy or slate, medium charcoal or grey. Logic: three pieces suits offer flexibility to wear as a two-piece in various ways.
  • Chino’s/Khaki’s, reach for blue, grey, slate, olive and burgundy tones. Logic: comfortable but colors are more modern and versatile.
  • With shirts reach for your simple white, blue, grey, muted colors, even a lavender tone.
  • Shoes don’t have to be expensive or custom but take good care of the shoes you have. Logic: ‘Shoes are a piece of art’ says Kinnebrew. It’s nothing worse than having the perfect outfit, and the shoes are worn down or dirty, throws off the entire look.

Kinnebrew acknowledges that many companies are moving toward the business-casual model. If you happen to wear jeans to work, go for a more well-fitted and dark denim look. The logic behind this one is simple: it’s more professional. He also emphasizes to put effort into how you look while at work. It is where you spend much of your time a day, so why not look good and collect a check at the same time? Even if you aren’t at the point of purchasing custom garments, Kinnebrew notes that you can always find good deals at department stores and while thrifting, you can always find vintage steals! The significant takeaways Kinnebrew says is to ‘do you and look good.’


Calculated Risks

It’s not all fashion and style with Kinnebrew, as someone who decided to ignore the safety net and take a risk— it is essential to emphasize how calculated those risks are. You’ve realized your 9-5, corporate hustle is not your true calling and the lack of passion is evident to you and those around you. What is your next move? “Follow your passion, do it in a very strategic way, so you are covered if anything were to happen” suggest Kinnebrew. Many of us know how difficult it is to overlook that safety net that keeps our bills paid and food on the table but are you missing the opportunities in the grand scheme of things?

Even if you aren’t ready to jump just yet, build up your knowledge base, craft, and experience so if you were to leave, or in Kinnebrew’s instance get laid off, you already have a leg up.

“Sure, the grass is greener on the other side,” says Kinnebrew “it could also be dead and need watering. It takes a lot of soul-searching to get comfortable with yourself and what you want to do, but don’t forget to take [calculated] risks along the way.”

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