Coolest Person in the Room: Jake Fleming

I’m always so curious when I talk to content creators about what it took to go viral. Was there a specific moment that you remember when your videos started to stick?

I didn't start that long ago. It's only been a little over two years now. I started on TikTok, but it just wasn't working for me in the beginning. I was kind of trying to follow the trends of that time, when COVID was just ending, and I wasn't finding my own unique footing so it wasn't working. I kind of gave up because no one was watching anything. Then a few months later, I was like, Let me try this again. I started talking and showing my personality, and that's when I noticed that it started clicking. I got my first video that had a million views, and I was like, Oh my god, here we go. It kind of just spiraled after that. Always show your personality.

Personality is what really is what makes someone cool!

I feel like my personality is kind of niche in the grand scheme of people creating fashion content, because a lot of people are more mysterious and dry and don't really show their personalities, because that's what sells. It was more fun for me to pave my own little avenue of the internet. and it was well-received. Thank god.

What do you think is that little avenue of yours?

It’s the relatability and the not-so-stuffiness of the fashion industry that people can relate to. It makes it more fun and lighthearted, rather than this untouchable creature that just wears designer clothes all the time. Like yeah, I wear designer clothes all the time and work with designer brands that are in itself untouchable, but I make it more relatable by just being like a friend on FaceTime in my videos.

How did you find your personal style?

It's definitely been gradual over time. Even when I look at stuff that I wore two years ago, I'm like, Oh my god, that's horrifying. I wore so much color before, I figured out that was definitely not for me. But now I figured out what silhouettes, materials and brands I like. I wear a lot of Japanese designers like Yohji [Yamamoto], Comme [des Garçons]. I have big collections of that type of stuff because I fell in love with it. I kind of muted all the colors in my closet, so now I really only wear black, white, some neutrals here and there, darker versions of blues and greens. Everything's very dark, but I think it also just looks better with everything [now] that I have bleached [hair and eyebrows].

It's funny because your energy is so vibrant, but then your style is avant garde and all black and white.

It's a nice juxtaposition because on the surface, I might look not very approachable. But then I open my mouth, and I'm like, “Heyyyyyyy!”

Did you have experience in the fashion industry at all before?

No, I hadn't stepped into the fashion industry at all. I did go to fashion school in LA. I went to FIDM, and then I started posting online right after I graduated. I only went there for two years, though, and got my AA. I thought I was going to be a production assistant or working behind the scenes, but always in the back of my head, I knew that I was going to do this whole situation. I don't know how, but I was like, I'm gonna figure it out. And then it ended up working out.

Now that you’re fully in it, I’m curious about your perspective about the industry as a relatively new insider.

The business is crazy, and I didn't realize how crazy it was prior to getting into it. It's a very political industry, and you have to have a good grounding for yourself, or else you're going to drive yourself crazy and compare yourself all the time to a million different people that are doing the same thing that you're doing. It's hard sometimes to not get flustered by the things that are said; it's very nitpicky on people's images and body types and sexuality and all of that. I've even dealt with some things, like being flamboyant and gay. You would think that you would get praised, but it's not always like that. They want people that are commercial and not so avant garde all the time. But as things progress a little bit more, it's honestly gotten so much better. Like, if you look at the influencer/creator fashion industry, there was no one with personalities like five years ago.

How do we make fashion actually more fun?

If the older people that are still running things in these fashion houses become a little bit more open-minded on marketing and stuff like that, I think that's when we'll allow some more lightheartedness and fun. You see it now, even, with Loewe. They have fun. If you look at Loewe’s TikTok or whatever, their content’s fun. You don't see many other fashion houses doing that, because they want to keep that mystique. Brands have to find that happy medium, because fashion definitely is this pristine industry. So if you can make it pristine but a little goofy, I think that's like a good mix.

What does your day-to-day look like?

I try to keep things on a tidy schedule. That's just what works for me. On a typical day, I wake up around seven, just because my bedroom is very, very bright. So it's seven or nothing. We're getting up right then and there, and then I try to do a little workout before I do everything else. I plan based on if I'm going to film a certain amount of videos that day, and usually there's meetings over Zoom and answering emails. Right now, we're planning out all of fashion month, so my days have been spent doing the logistics for that and then shopping for looks for each day. Then I'll have my assistant come over, and she'll help me shoot and do things around the place, whether that's rotating the closet out, selling a bunch of stuff that we don't need anymore and getting new stuff going out to film.

I'm getting back into acting. My family's in the entertainment business, so I grew up acting, and now I'm getting back into it. So that's another thing that I do towards the end of my days, whether that's filming self-tapes or going to a class.

Is acting where you see this all going?

I see myself forming into more of a personality in the entertainment business as a whole, using the platform that I've been building to help push it there. I've been focusing enough on fashion the last two years to be able to start diving into some other things. Whether that's hosting things or doing mini series with some streaming service or working with brands as a personality instead of just a content creator, I'm ready.

I feel like everyone is kind of over the sterile, perfectly-curated breed of influencer.

As much as it is pretty to look at online, where does that end up going, at some point? I think with me starting with having a personality online, and people knowing me for me, it’s allowed more progression and growth.

Lastly, what does “cool” mean to you?

Being completely in touch with yourself and understanding your uniqueness. It doesn't matter how much money or fame you have. If you're just unique and authentic and living freely, that's what I think cool is. When you look at somebody that's really dope walking down the street, you can tell they just don't give a fuck. They're doing whatever they want, and they're so in touch with themselves. That's what cool is.

Photography: Diego Villagra Motta
Styling: Angelina Cantú
Hair: Chika Nishiyama
Makeup: Amelia Jackie
Nails: Jay Oh

Styling assistants: Joyce Esquenazi Mitrani, Mo Johnson

Editor-in-chief: Justin Moran
Managing editor: Matt Wille
Editorial producer: Angelina Cantú
Story: Andrew Nguyen
Location: Nine Orchard