There was a time when I would be on Twitter all day, every day. Back then I had an action sports clothing brand that I was trying to get off the ground called, Azz Monkey Clothing Carnivale aka Azz Monkey. While we were using the @azzmonkey Twitter handle I had the opportunity to chat it up with Fubu’s Damon John every now and again because he followed @azzmonkey for a little while. He asked me to watch a new show he was on called, Shark Tank. He wouldn’t give me details. He just wanted me to watch it. What did I do? Not watch it. At least not in the beginning. I started hearing more about the show as people started watching. I saw Damon on a Shark Tank commercial spot and remembered that he’d mentioned the show to me months earlier so I tuned in for a couple of seasons. I admit it. I’d became a certified “Shark Tank” whore. I watched the show not so much for the investement deals, but for more so for the innovation and the creative ideas that different entrepreneurs had been developing. There was one particular episode that featured a very blonde woman with an odd sense of style. She said that she was the Founder of a tech startup called, Cheek’d and that her name was Lori Cheek…

Panama: Lori!

Lori: Hey!

Panama: I thought that we would start by going back to where our friendship began.

Lori: Ok

Panama: I first saw you on an episode of Shark Tank. You know that I have a special place in my heart for real “Entrepreneurs and Founders”. Especially Founders of Tech Startups because I know what everyone goes through. I know the struggles and the obstacles we encounter when trying to accomplish something because I am also a Founder of a Tech Startup as well.

Lori: Yes

Panama: I immediately felt like I needed to reach out to you. I wanted to get to know you because of what you were doing with the Founding of Cheek’d and also because of what you were wearing on that particular episode. I’m thinking, “Man, that chick’s got some style.” Now, I did not know how much style you had until I saw pics of you and what you were wearing floating around on Google.

Lori: (laughs)

Panama: I was like, “Dope! I really like her style.” So, while putting this blog together I figured that I would first speak to the people that I knew personally. Secondly, reach out to people that were within two handshakes. Those are basically the friends of friends who I could either be introduced to or would probably end up meeting at some point in time when our respective circles or paths crossed. Then lastly, I would reach out to those that I did not know at all. I’d sort of sprinkle all of those talks into The Showroom periodically.

Panama: So for today, I don’t want to speak to you about Cheek’d, per se, but more about your style before Cheek’d. Now, I know that you use to work for a designer right?

Lori: Yes, I was an architect and for about four years. I worked as an in-house architect for Christian Dior.

Panama: Right. So how did that influence your style?

Lori: I’ve always had a kind of quirky different sense of style. I grew up in a town of two thousand people and there was something about me that was always different than everyone else, you know? I made my own clothes, I was in 4H and I just had this funky sense of style from as long as I could remember. My grandmothers had this fabulous sense of style too and they had all these hats and shoes. Every time I would be at their house I would be in their hats and shoes and jewelry boxes so, I don’t know. Fashion’s always been something that’s been was in my blood.

Lori: Working for Christian Dior was like a dream come true. It was always my favorite brand back in the day and John Galliano, who was my favorite fashion designer back then, was the designer for Christian Dior. Like, I couldn’t even believe there was an architecture job open and that was my way into one of the most fabulous fashion houses of all time.

Panama: Absolutely

Lori: I got a pretty amazing wardrobe. You know, they would have employee sales and sample sales and all kinds of great perks, and contests, and gifts, and I just had this amazing wardrobe after being there for four years. Yea, I think it jacked up my sense of style to a more luxurious version of who I was before. I just didn’t have access to that before.

Panama: A very big enhancement to what you were already doing.

Lori: Exactly

Panama: Was it your grandmother alone that had inspired you? Or was it other things? Or other people?

Lori: Well it was both of my grandmothers. Like, I love going to grandma’s house because they just had the most fabulous matching jewelry sets, I mean, it was just fabulous to be at their houses. I could spend hours in their drawers and closets. I mean, they use to have all these fun capes and scarves and you know, people don’t dress like that anymore.

Panama: No, not at all, not at all…

Lori: But I do! (laughs)

Panama: Yea, and THAT is the reason that I wanted to talk to you about it. Everyone that I’ve spoken to or want to have interviewed for The Showroom is for that particular reason. There is something about their style that I like or there’s some product they created that I like. Speaking of which, there’s a picture I’ve seen of you rocking a plaid wool jacket, a hat with a feather, and a necktie. I don’t know what to say about the hat. You simply killed it. Nowadays, people are really becoming “Sheeple”. They are so easy lead like sheep to follow ANY trend that comes out and their afraid to just be themselves and do something different.

Lori: Well, thank you! And you know that hat has a really interesting story. When I was talking on “Shark Tank” about everything I’d given up, I had moved out of my West Village apartment and rented out my apartment on AirBnB for fourteen months. Three of those months I lived in this apartment up in the depths of Harlem and I found this consignment store that I use to find the craziest stuff in. That hat was in there with a tiny broken feather on it and I went to the fashion district and found the biggest feather I could find that wasn’t going to knock people out in the subway.

Panama: LMAO

Lori: I adorned that hat with that huge feather myself. I paid like, $15 for that hat and you would not believe the attention I get on the street with that hat.

Panama: Oh, I’m sure! My daughter Cassie saw that picture and said, “OMG, I love that hat. I love that hat. Dad, tell her I love that hat.” So I’m like, “Yea, I’ll tell her.”

Lori: I’ll will it to her when I move on to the next life, lol.

Panama: (laughs) Ok. She would love that too. She would rock it.

Lori: (laughs)

Panama: When was the first time you’d ever felt good about a look you put together? Can you remember that?

Lori: I mean, I’m telling you, I have always been into fashion. Like, even in elementary school. My seventh grade picture is so funny. I have on a purple button-up shirt with a purple polka-dot tie and glasses.

Panama: LOL

Lori: Yea, I was wearing ties and gold jewelry back then and it’s so funny. That tie thing has been around forever. I’ve always been inspired by men’s fashion with a little bit of gangster bling meets very feminine 40’s chic so yea. You know, I can specifically remember when you had your school pictures taken, I remember for days I would lay out all of the outfits I wanted for the photographs.

Panama: What trends do you think are timeless?

Lori: I do love the 40’s. I feel like all fashion that I have loved and admired back from my grandmothers to this day and age is tapered men’s suits and thin ties. I like wearing pins. I don’t think people like to wear pins anymore. I love “Great Gatsby” fashion, you know? Just anything kind of old school with a modern twist. I like wearing 40’s glamour with a little bit of Jay-Z or like, gold stuff. I’m really into black and gold too.

Panama: What trends would you like to see go?

Lori: Well, I just think it’s funny that, you know, my mom, she really knows I’m into fashion and she’ll call me sometimes and be like, “Well, I saw the new thing on Good Morning America was blah, blah, blah. You know, this is the new trend of the season.” And I’m like, “Mom, you know I’m the Anti-Trend.”

Panama: LMAO

Lori: If it’s a trend, you know, I walk the other way. Trends are trendy but then they become the norm. But I don’t know. I honestly can’t think of something that I really want to see go away right now. I mean, I just remember the worst look ever was the shorts and those UGG boots but that was from times past. Oh, and those Crocs! But those are gone too. (thinks) Yea, I can’t think of anything that irritates me at the moment.

Panama: That’s why you and I are so connected. I’m an Anti-Trender myself. If the masses are going to the left, I always try going to the right. For the most part, I do not like to wear or do what most are doing because you would never stand out. You stand out when you make bold choices and decisions like, “I’m not going to wearing “Hammer” pants again. You guys can wear them but I’m not wearing those shits again.”

Lori: Right (laughs).

Panama: I mean, some of the trends they have now are alright but I just try to do my own thing. I know this might sound counter-intuitive but I try not to let any fashion or style person “Jedi Mind Trick” me into some of this bullshit that I’m seeing today.

Lori: Exactly

Panama: Where do you go shopping?

Lori: You know, when I hit that financial wall a long time ago, I ended up selling my Dior wardrobe to help fund my business. I haven’t really shopped in serious stores in ages. Now I find myself in TJ Maxx or Marshalls or cheap stores all over New York. But I don’t think that money matters. It’s just like, if I see something that I like, I get it. It could be $10 but I think I make it look like its $1,000,000. It’s just in how you wear it. My brother gives me a $75 TJ Maxx gift card for my birthday and for Christmas because everybody knows they can’t shop for me. That’s my main shopping budget. I also have a lot of credit on Amazon.com so if there’s stuff that I really want I usually order it from there.

Panama: How is your sense of style different from your girlfriends?

Lori: None of my friends really dress up outside the box at all. And that’s how I think I differ. I mean, my hair is this crazy bleach blonde and its almost like I can’t hide. Not that I want to but people can see me coming from a mile away. I think that a lot of my girlfriends are pretty conservatively dressed. I mean they’re dressed nicely but they would never be caught dead in some of the crazy outfits that I step outside of the door. Again, they all have corporate jobs and maybe can’t dress the way that I do but I think its all part of my character. I live and breathe my business and my image. I just have a really fun time getting dressed and I’ve got an awesome closet filled with all kinds of fun things.

Panama: Oh, I know this. Any woman that can wear a pair of wings and get away with it is cool with me.

Lori: LOL, those wings have gotten me in Forbes Magazine.

Panama: Really?

Lori: Yes, I was on the cover of the Irish Times with those wings too.

Panama: I guess bold choices can get you places. Maybe people need to know this. Stop wearing that same shit.

Lori: Everything comes back to my business, for me. Even the way I dress has landed me in the news for my business.

Panama: What advice would you have for those that I have not found their “Style Voice” as of yet. Maybe they don’t know how to put an outfit together. Or perhaps they are afraid to step outside of the box with bold choices.

Lori: When I use to be an interior designer and people didn’t know how they wanted to design their homes. I’d tell them to flip through magazines and pull out pages of things that they liked. If you just wad it all up together that’s going to be your style. I think it’s similar in fashion. I usually get inspired by people off the streets. I don’t get inspired by people in magazines. You know, I’ll see somebody wearing some crazy furry slippers on the street and I will stop them and find out where they got them. Overall, I think it’s just about being bold and taking chances. Paying attention to the things that you like and maybe even keeping a little scrapbook. It’s a little hokey but it could be an inspiration finally if you start tearing out looks that you like, or making notes about things you saw on the street, or asking people where they shop that you admire their fashion. It’s about baby steps. If you want to do something bold I’d say don’t walk out the door wearing a garbage bag. Just take little steps towards finding who you want to become in your own fashion sense.

Panama: Ok, doll. Thanks for sharing with everyone. Don’t forget, the next time I’m up top in NYC and you are in town and, not in Kentucky, we’ll have to hookup for drinks!

Lori: Yes! Yes!

Vist Lori Cheek on Instagram

http://www.networkd.io and http://www.cheekd.com