The fashion industry may be filled with content creators—but few know their history and context like Jake Fleming. After studying design and working with influencers, Fleming’s distinctly romantic goth-meets-prep chic personal style propelled him to social media fame. Now, he’s become a darling of brands from Fendi to Moschino—and proves that knowledge, genuine enthusiasm, and a little (or a lot) of humor can go a long way online. Hundreds of thousands of followers and industry insiders now watchfully take in his animal bag collection, viral videos with Donatella Versace, and stylish jaunts across New York, Milan, and Paris. We hopped on a call with Fleming to hear all about his lifelong love of fashion, recent runway highlights, and musings on fashion’s future after 2025’s whirlwind designer shuffle.
Jake, how did you get started in fashion—and how did that lead to becoming a content creator?
I started in fashion school. I went to FIDM in LA for two years, and I had no social media presence while I was in school. Once I graduated, I was trying to figure out what I could do with this degree. Nothing was screaming at me, and I was like, “You know, I’d rather just be my own boss. I need to stop thinking TikTok’s cringe.” I started posting a lot of fashion commentary on TikTok, and it didn’t hit at first. It took me awhile to get an audience and grow. I took a break—I would post, then I stopped, and then life happened. I went into this really horrible relationship, and that’s also what re-inspired me to keep posting. He robbed me, and I was down bad—I needed a job, and I needed something that was creative. So, I started posting again—and the second time is when everything started working out. I gained 100,000 followers on TikTok in my first three months of doing it. At that time, I was working at a creative social media agency, and I was able to stop working at that agency within maybe five months because I was able to monetize social media.
Jake Fleming (Courtesy of Jake Fleming/Instagram)
What did you study in school?
My degree at FIDM was in merchandising and product development. It was like a mix of fashion design and business in one major.I definitely wanted to be on a design team, whether that was as a production assistant or building my way to being a creative director and having my own brand. That never ended up happening because social media started, but now I’m able to use the stuff that I know now for creating my own brand, which is great.
Do you still have an itch to get into design?
Yeah! I have my vintage store, and we’re doing a huge collaboration with eBay. Just know that there’s a project coming, and the vintage store isn’t going to just stick to vintage. My business partner and I have a really clear plan of creating our own ready-to-wear line that’s based off the silhouettes from vintage clothing that we love, that you don’t see too often anymore.
Dev Apollon, Jake Fleming
You have a lot of fun with fashion. When did you find your personal style, and how would you describe it?
My style has changed a shit-ton, especially within the last year since I dyed my hair brown. It used to be very black and white, very edgy. I would only wear Comme des Garcons or Ann Demeulemeester. Now, my horizons have broadened, and I’m tapping into more color and masculine silhouettes. It’s been great. I feel more aligned with what I’m wearing now than what I wore when I had bleached blonde hair. I’m loving this new era. I definitely stick to brands that speak to me the most in whatever time of my life I’m in. Right now, I would say it’s McQueen and Dries Van Noten. I wear so much vintage clothing that it’s hard to pinpoint which brands I’m wearing a lot. I still wear a lot of Ann Demeulemeester, and a lot of contemporary brands like SYSTEM and Our Legacy. My favorite brand right now is Stefan Cook, he’s pretty new, and his stuff is so good. I keep finding myself gravitating towards him. In a more accessible realm, Massimo Dutti is great. I wear a lot of COS.
Jake Fleming
You just filmed some fun videos in Donatella Versace‘s home, which she appeared in and collaborated on with you. Tell us about that!
It all happened because of Instagram. A little over a year ago, I posted this video wearing this vintage Versace blazer. I didn’t even tag Versace in the video, so the way that it showed up on her timeline was completely organic. I posted in this blazer, she ended up commenting on the video and following me. On that video, she commented that no one has worn the blazer better. I was like, “What the fuck?” With that information, I contacted my reps over at Instagram, and was like, “Hey, could we make something happen with her?” For her last show, they invited me to Milan to meet with her. She showed me the collection before Anna Wintour, which was nuts. We filmed our first video that we ever did together meeting for the first time, and the video got 70 million views, which is insane. That led to us becoming friendly, in a way. She gave me a call before I was about to head to Milan Fashion Week this season. She was like, “Jake, come over to my house. Let’s have dinner.” We talked about some things that we want to do together. But the appearances of Jake and Donatella are not stopping anytime soon, because we’re attending a little awards show that’s coming up.
Donatella Versace (Courtesy of Versace)
Fab! Did you have a favorite part of her house?
All the artwork and the photography in her home. Obviously, she’s Donatella Versace, so all of her family photos are shot by Helmut Newton, Peter Lindberg, all the most iconic photographers that you can think of are all over her house. It was really inspiring to see how much history is in her halls.
We also understand you have an Instagram show coming out soon!
This show was inspired by the original video that I did with Donatella, where I went to surprise her and us meeting for the first time. The concept of the series is based off of that. Instagram and I have a really great relationship, and I had pitched this idea to them. They didn’t even hold back, so I have the help and support of Instagram to create such a sick show like this. It’s basically a fashion docuseries where I interview my favorite creative directors, celebrities, singers, actors, basically anything you can think of where somebody is a public figure, shadowing them in a day of whatever they do for their job, whether that’s a creative director doing a new collection, a singer on tour, or an actor that’s on set.
Jake Fleming, Zoi Lerma (BFA.com)
Who are some designers or fashion figures you look up to?
One hundred percent, Jonathan Anderson. He has such a vision. Everything he does is so up my alley. Same with Alessandro Michele. The two of them create clothes that I would sell my soul for. Thankfully, now that I have adult money, I can support their endeavors as much as I possibly can. Everything that they do inspires me a lot.
Why is it important for you to fiscally support different brands when you’re able to—especially since content creators usually receive or request these as gifts?
It’s important because you’re supporting somebody’s creative ideas. Sure, a lot of these big designers are conglomerates at this point, but you’re buying into their vision. That’s just something I like to do. I like to encapsulate myself into somebody’s vision. Being able to buy designer clothes and wear them how I envision them is something I always dreamt of doing as a kid. I think I’m just fulfilling that dream of mine that I had as a child. Being able to do it comfortably now makes everything feel a lot more fulfilling.
What was your first luxury fashion purchase?
My first big fashion purchase was a pair of Balenciaga boots. This was during Demna‘s era, because during his era is when I started doing social media. They were these pair of heeled black leather boots that I ended up actually selling after a few wears, just because I realized I really was never going to wear them. They were these trash bag-looking leather boots that tightened around your calves. That was the first big purchase. I think they were $2,400. Soon after, as I continued this career, I was able to buy a lot more different things.
Jake Fleming (Courtesy of Jake Fleming/Instagram)
You’ve gone viral for your collection of novelty animal and item-shaped bags. How did that start?
It started when I started buying Jonathan Anderson’s animal purses. I bought the frog and the pigeon when he first released them. I was like, “Okay, this might turn into an addiction now.” Then, slowly but surely, it started. More and more brands kept making them, I kept buying them, and I kept posting them. Social media pushes your stuff out, so all these brands, were like, “Why don’t we just send Jake these bags, since he collects them?” Now, I’m at the point where I rarely have to buy bags anymore. They just show up to my front door every week, and I wait to see what shape or object is going to be. I did a collaboration with Moschino last summer, and those were some of the most viral videos that I did, with crazy Moschino bags. As we know, Moschino creates some insane object bags. It’s been fun for me to collaborate with brands solely based off something I started as a little hobby. Now I just have them all over my apartment.
Fleming’s J.W. Anderson pigeon bag, named Patricia (Courtesy of Jake Fleming/Instagram)
What’s missing from your bag collection?
There are a few Loewe ones that I want. There’s a lemur and there’s an elephant that I don’t have. There’s actually a wicker elephant from Loewe that I would absolutely love to get. Also, the Loewe tomato. I really, desperately need that. I’m also excited just to see what Jonathan [Anderson] is going to do, if he does any weird animal bags over at Dior. We’ll see what happens there. The possibilities are endless for what I need, because some of these things show up and I’m like, “I didn’t even know I needed this, but I love it.” Cult Gaia sent me a clutch that’s shaped like grapes. And I was like, “Oh, shit, I didn’t even know I needed this.” It’s one of my favorite things to look at. I love it so much. They also sent me a bag that’s a vase of calla lilies, and the video I made with that bag is one of my most viral videos ever, with 20 million views. It’s crazy that this has become somewhat of an avenue for me now. I have broken a lot of the bags that I have; a lot of them are ceramic, and are not meant to be dropped on concrete. I’ve shattered most of my JW Anderson bags because I actually use them. I’m very clumsy, and I was out one day carrying my Puffin bag that I purchased from JW Anderson—that, mind you, was $840. I dropped it and it shattered into bits on the ground in the Lower East Side. Like, “Really, this is happening right now?” Oh my God.” There’s a gold fish bag that this small business The Vin sent me, and they’re having a little moment online after I posted. It’s a brass fish, and I think it’s one of the coolest pieces that I have.
Jake Fleming (Courtesy of Jake Fleming/Instagram)
There’s something so whimsical about a tiny bag.
There really is. It makes fashion more fun. I love the juxtaposition between wearing an outfit that’s really chic and then adding something that’s a bit crazy, like an animal bag. If the bag’s small enough, I use it as a wallet, or just as a little pouch inside a bigger bag. I just purchased my first Birkin. I use a lot of my animal bags as different pouches inside the Birkin to hold any beauty stuff.
What’s in your Birkin?
I’m carrying all of my EpiPens, because I’m allergic to nuts. Every nut—kiwi, pomegranate, the list goes on. I’m carrying around EpiPens and inhalers. I have a little Aquaphor lip balm, some Caudalie Beauty Elixir face mist, maybe a little bottle of [Maison Margiela] Replica, By The Fireplace. I have some journals in there, my Acne Studios wallet, my Apple headphones, keys, and maybe a little snack.
What were your highlights from Fashion Month this year? You hit New York, Milan, and Paris for the Spring 2026 shows.
As we all know, this was such a big year for fashion. There [were] so many people’s firsts at these brands. It was a very exciting season overall. But the two that I feel stick out to me the most were Louise Trotter at Bottega Veneta, and Jonathan [Anderson]’s women’s at Dior. Oh, and Dario [Vitale] at Versace. Those three stuck out to me the most personally, and I loved all three of those collections. I know a lot of people hated on Dario’s vision, but for me, being such a supporter of Versace, I think the vision is there, and the styling I really enjoyed. It was a really cool way to do something new for the brand. I obviously know that it’s completely different than what Donatella was putting out, but I’m excited to see where the brand is going to go at this point.
You also made an appearance at the Victoria’s Secret Fashion Show this month! What was that experience like?
I always FaceTime [my mom] on my way home, which is what I usually do after a fashion show. I give her the rundown. But me and my friend Renée, who was sitting next to me, were screaming our heads off the entire time. Her and I had a few friends that were in the show, which was also a really full-circle, really fun thing to witness. We were screaming at everybody, cheering them on. It felt such a great, empowering moment for all different walks, different types of women. It was really sick to see. I love that Victoria’s Secret is focusing on different body types now. I think the inclusivity of the show is amazing.
What’s been the biggest difference between living in Brooklyn, versus living in Manhattan?
I love Brooklyn! It’s so much homier here. When I need to go into the city for work, I do that, and then I get to go home, and it’s calm. The area of Brooklyn that I live in feels like I’m in, a fall ’90s rom-com. It feels like everything’s perfect. It feels like I live in Gilmore Girls. The street is so goddamn cute, the brownstones and all the surrounding areas are so nice. It motivates me to be in the neighborhood and not feel like I have to go explore somewhere else. I feel comfortable where I’m at.
Jake Fleming (Courtesy of Jake Fleming/Instagram)
What are your thoughts on the creative director shuffle this year—and how do you think it’ll affect fashion as the 2020’s continue?
I’m not sure I understand what the big parent companies are doing. However, more women need to be creative directors, especially for these houses that are so focused on womenswear. We get that men can design, but we know that women obviously know women’s bodies more than a man does. We’ve got to throw some more women in there, especially women of color—let’s talk about Miss Wales Bonner going to Hermès. That was such a grand moment, especially for a heritage house. That was the happiest day of the year. I almost forgot about all the stuff that happened during Fashion Week, because that’s what we have been needing. Teams [also] need to be in touch with what’s happening economically. More people are buying into the secondhand market than buying new, which is great, because we need to be more sustainable as a society. From what I hear and read, people are not investing in luxury fashion as they once were, which I think is why brands are shuffling creative directors to clean out and create new imagery for these brands that may be struggling behind the scenes, which we as consumers don’t necessarily know about. I’m on the sidelines watching, like, “Is luxury fashion going to stay around forever? What’s going to happen?” People in the state of the world right now are not wanting to spend $5,000 on a goddamn jacket. We both saw the trunk show prices of what Tom Ford and Versace were selling. You have to make luxury fashion more accessible, to a point. There’s always going to be that mystique and envy about luxury fashion, which is what keeps it where it is. But at some point, you’ve got to give. I’m excited to see if that’s going to happen, and what is going to happen with these brands that are fighting to stay afloat.
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