Jarrett Bennett: Personal Style & How I Developed Mine

This is a guest post from: Jarrett Bennett.

My journey to finding personal style began in high school. As I stated before, I was the kid who would always try out different things. I remember for an extended period of time, I was big on converses. This was like the Wiz Khalifa “Taylor Gang” era. I think I may have had at least ten pairs. I’d wear them in a different way almost every week. One week it may be a solid colorway, the next it may be two different colorways at once lol. 

As time went along, I got more into actual clothing. I achieved my first pea coat my sophomore year of college. That’s really where I developed my love for Autumn/Winter wear. You never really saw me arrive on campus without it. I actually still have that jacket now. My brother Q. Winchester is currently working on it. In college, a lot of times I would be the first person wearing something. From grey joggers when they first blew up to Chelsea boots, and got clowned for it. I got called things like twinkle toes, ballerina boy, clown boy, things like that. The next year, everyone was wearing them. I was the first person to have an authentic pair of Gucci flip flops on campus. The following semester, I saw at least ten pairs.  One day I thought that I should try something different, so I started to do some research. 

One celebrity that played a part in my search for personal style was Kanye. My favorite eras of Ye were 2008-2015. That was like 808s & Heartbreaks – Yeezus. I felt like he was really in his bag then. Mixing both menswear with streetwear, while making it look clean at the same time. Hearing him mention brands such as Hermès, Yves Saint Laurent, Louis Vuitton, and Versace in his music, made me want to know the type of product they released. 

Before that, I didn’t know what “luxury” was 

One of my favorite versus he created was a line from American Boy x Estelle: “Dress Smart like a London bloke. 

Before he speak his suit be spoke.

And you thought he was cute before

Look at his PeaCoat, tell me he’s broke”. Next thing you know, I was wearing denim shirts, camel cashmere overcoats, biker jackets, and any OG Air Jordan (1s, 3s, 4s, 8s) silhouette I could find.

After I got out of the “Ye” stage, I decided that streetwear isn’t really a look that I would go for down the road. I personally like menswear more than streetwear. It’s something about popping out in a suit, and styling it to make it more casual, as opposed to just putting on a box logo supreme tee that’s overhyped. Some of my favorite menswear designers are 

Tom Ford, Hedi Slimane, Rick Owens, Raf Simons, Ralph Lauren, Marc Jacobs, and Dries Van Noten, J.W Anderson, and Samuel Ross just to name a few. I honestly can’t count on my fingers nor toes, the amount of collections I’ve watched. 

Once I found my personal style, I started following people on Instagram and Twitter that I thought could help provide information about menswear/womenswear that I didn’t know. As a fashion consultant, you have to understand how to style men and women. Some pages that I follow and actually have had conversations with are @Pam_boy , @LondongirlinNYC, @henson (stylist for A$AP Rocky), @thecrediblesource, @sirjoslin, and @coreytstokes . By reaching out to these people, I learned difference between good styling, good taste, and something that’s trendy but won’t last. Research is very important when finding your personal style. 

For a while now, my favorite era of fashion has been the 1960s-1978, with a skip to the 1990s of menswear. It’s funny because fashion today, seems to be circulating back to those time periods, and I’m completely here for it. You just have to put your on twist on it ya know? 

Style is different with every person. Some people would prefer sneakers over a loafer or dress shoe, and vice versa. I personally own more loafers/dress shoes than sneakers. The last sneakers I purchased were my Saint Laurent Paris Court SL/10h’s. Not going to lie, they cost me a steep price because I paid for them brand new. I do believe in buying what you want, but being smart with it. 

The amount of money you pay for something, doesn’t automatically show you have good style. I’m a big fan of thrifting. You can have a lot of money with no style. It’s possible, look at certain celebrities. Good style is either a hit or miss. Either you have it or you don’t. 


Follow me on social media: Twitter & Instagram.

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