Interview by Carol Wright | Photographer: Sara Anderson Davis
Diana-May’s love of shopping has taken her to unimaginable heights. After quitting her full-time job to pursue content creation, she has worked with major brands like Steve Madden and has a loyal following of people who scroll through her page for outfit inspiration. Kirori hopped on the phone to talk to NYOTA about how her environment influences her outfits, not asking people for their opinions regarding clothes and being intentional about the items she buys.
Social media helped spark your interest in fashion. What was it about the content you were seeing in those early days that caught your attention?
That’s a great question because I don’t even know if it was the content that inspired me. It’s hard to say what really drove my aspirations toward fashion other than wanting to shop. I love shopping. I love clothes. I think it comes really easy to me, and I realized how easy it came to me when I sat down with someone. I’m like, ‘Well, this just makes sense,’ and he was like, ‘No, I would never know how to do that or why to do that or why to pair this with this,’ and I think it’s just something that I get on with so well, and it just clicks for me, which I really enjoy, and it brings me a lot of joy. I feel such a sense of accomplishment when I put an outfit together that I love. But in terms of social media, when I was younger, I followed bloggers, like your classic 2012 bloggers, which is really funny to think about now, and wasn’t really on social media in terms of following influencers and whatnot. Because I was also hesitant to download TikTok, I would make my sister save all the funny TikToks for when she got home, and we’d just scroll through them together. Then, as for Instagram, it was maybe a handful of bloggers that I followed, and I wasn’t on YouTube either, and I was never a YouTube person growing up. I only knew of YouTube because of my friends who were obsessed with it. So I didn’t even discover people that way either, and then I just decided to get on TikTok myself later in 2021. Through me getting on social media, that is how I was exposed to it even more.
Instead of slowly easing your way into content creation full-time, you took the bull by the horns, quit your job, and moved to London. Did you have anxiety around making such a significant life change, or did it feel so right there was no questioning the decision?
I didn’t put too much pressure on it, and I know people are always like, ‘You’ll know when the time is right.’ I don’t even know if I felt any sort of way. I still think that even if it wasn’t for my job saying that we had to be in the office five days a week, I would have quit eventually. I don’t think I was the type to be like, ‘Oh, but this job is stable, I want to keep it.’ No, I didn’t want to do that. I love the freedom of working for myself, so it’s not something that really held me back, but I knew that that was the decision-making announcement because I could not continue to do social media and be in the office five days a week. So I was like, ‘Well, I guess I have to do it and figure it out.’ Corporate America will always be there if I need to go back. There was not really a big tipping moment – should I do this or should I not? I was like, ‘Well, it’s either this or what?’
Finding one’s sense of style takes time because you must experiment, wear the “bad” outfits, and understand what you gravitate to when shopping. Nowadays, we’re losing that fun, experimental journey due to clothing trends blowing up on social media. Is there one piece of advice you have for people who tend to go trendy versus authentic when it comes to their style?
I think the biggest thing would actually be to stop asking people for their opinions. Like, ‘What do you think?’ ‘Do you think this matches?’ Whatever you put on, just go with it. I look back at my outfits where I just went with it, and I’m like, well, now that’s ugly. I think that’s ugly. What was I thinking? But without that and without looking back on my outfits, I would have never grown into who I am today in the way that I dress, so I think that’s the biggest thing ever. And I even catch myself going to text my friends. What do you think about this? First of all, what do I think about it? I don’t know why I need their opinion all the time. So that’s my biggest tip, which is to stop asking the crowd. On social media, it’s really easy to get that way, especially as a creator; it’s an engagement thing; you’re like, ‘Guys, which one should I go with?’ Another tip would be to dress for your life because I find a lot of people are just dressing with the trends, and I’m like, okay, well, you’re not wearing a faux fur jacket to the construction site. This doesn’t match up, but it’s definitely just dressing for your life and not for social media trends, essentially. I also think it’s hard, though. Sometimes, you have certain events that you need to dress for, and I totally get that, but for your day-to-day life, which is what you’re getting dressed for most of the time, I would just say to stick to that.
Last year, the Sweets & Sneaks series was fun to see come to life. Do you have a process for thinking through new series ideas and ways to make your content stand apart from the pack?
When I first started social media, as in TikTok, mainly because Instagram is the same, there was more of a creative process for me behind TikToks. Well, sometimes, because sometimes you just post. That’s the fun thing about TikTok; it doesn’t have to be thought out all the time. But when I first started, it was definitely heavy into fashion, and I know that’s what my platform was really started on and what people really followed me for, and all my videos were basically about different outfits to wear for different events and different things like that. But as I started to grow, I was like, ‘Okay, I do want to take this into more of a lifestyle and fashion; I want this to be a well-rounded page.’ And I didn’t always want it to just be fashion; I’m not in the business of creating my own fashion brand or doing anything like that, but it’s just something that I happen to be really passionate about, but I also love everything else, life and style. So I kind of started creating around that, more so vlogs, and those also do well, and vlogs can translate to YouTube, which is really nice. So, if I ever wanted to start long-form content, which I did, there was longevity in starting vlogs on TikTok as well. So I think I just wanted to start incorporating more life into my fashion content, which kind of led into all these other avenues, and then from there, I’m like, ‘Okay, what series could I start?’ Because I feel like any manager will ask you, ‘Do you have a series?’ ‘Do you have a specific series that people go to you for, that you’re known for?’ So, having a shtick is something. So I always try to look for something just a little bit different, like sweets and sneaks. I know that’s really personal to me, and I know it aligns with me really well. My audience would understand why I would be doing sweets and sneaks because I talk about those two things all the time, and I love them both. So I’m always trying to find something that is meaningful to me or would make sense for me to share in terms of a series or whatever it is really. And I think the longer I’m on social media, the more comfortable I become with kind of sharing anything, not anything, as in I share everything, anything in terms of I don’t box myself in as much. I’m just going to share this today because I feel like it, even if it’s not a series or something like that. So really just more of sharing my life essentially and day-to-day things, and of course, I’m always looking to see where brands can intersect into my content, and I’m like, ‘Okay, so if I post this, how’s it going to push the needle for working with different brands?’ So there’s always that in the back of my mind.
You’ve lived all over, from Chicago to Paris to London. How has your experience spending time in these cultural hubs influenced your style?
It’s so interesting because when I was in London, I had comments on social media, not bad ones. People were like, ‘Oh my gosh, you dress like a London girl, you’re really starting to dress like a London girl,’ etc., etc., which is so funny, but I do feel the shift in my outfits, but I also think it’s because I am dressing for what I’m doing for where I’m at for all those things. So, being in bigger cities, obviously, I’m wearing more sneakers because the city’s walkable. London, it’s cold, it’s rainy, I’m wearing more pants and sweaters and different coats, and it changes a little bit, but it’s still how I would usually dress; I’m just dressing more so for my environment. Paris was similar, but Paris was very warm when I was there, so it was just my sundresses and sneakers. It’s really, really inspiring to see the way other people dress in different cities. I love it so much. I remember that for the first stint that I was in London, I was in an area called Stoke Newington, and I watched everyone walk by on a Saturday afternoon, pushing their kids in strollers. I’m like, ‘Wait, you guys look so cool.’ You guys are in your 30s, with a two-year-old (that was the demographic), and you look so cool, and I just loved it. So, yeah, it’s influenced the way that I dress when I’m there, especially, and obviously, I take it back to whatever city I’m in.
I loved your Spotify Wardrobe Wrapped for 2024. With overconsumption being the talk of the town in recent years, it’s a perfect way to track loved or unloved items. As someone who has an interest in fashion and shops frequently, what are your methods for aiming to buy items you know you’ll 100% wear?
I’m in a lucky spot where I really know what I want to wear. Granted, that could change, but I feel confident about what I’m buying. And even lately, in the last two months, I’ve just been shopping around because I was in New York, I was in London, and I’m like, I don’t want to buy anything. And it’s so interesting because I’m like, I’m not buying just to buy anymore. I feel like before, I’d be like, ‘Oh, this could work,’ or I could figure out a reason, you know, I could justify anything. I’d really just be like, ‘Okay, this is a cute sweater, I’ll buy it.’ Now I’m like, that’s just not exciting to me if I don’t love it and if I’m not just so into it, and I think that makes it more exciting when I’m shopping because I’m shopping so much less or I’m buying so much less. I’m still out and about shopping, but I’m not purchasing goods. It’s so exciting to come across something that I really, really love. So I think it just comes with time and repetition and wearing my clothes, like wearing them over and over and over and restyling them, and then I keep a running list of what I actually want to add to my closet, and I’ve had the list for two years now, I want to say. And it’s just things I keep saying, like, ‘Oh, this would pair well,’ or I gravitate towards this one piece. And it really rings true when I add it to my closet; I’m like, ‘Oh, this feels good, this feels like a complete puzzle.’ But I’ll keep it on my list for months or for a year or a year and a half until I find that item. And obviously, if I don’t want the item by a year, then in a year, I just won’t get it, but that has also really, really helped because I just look at that list before I go shopping, and I’m like, ‘Okay, what do I actually need versus what’s new and exciting and I might want right now, but I don’t want later?’ Also, as a creator and someone who gets sent PR, it’s really, really important to say no to brands. And I used to feel guilty about it all the time. I’m like, ‘Oh, that’s so kind, I’ll just accept it.’ But I’m like, it actually doesn’t matter, it’s fine, you can say no. So I’ve had a lot of discernment of PR, which has been really nice because now I don’t feel so inundated with stuff. But it’s also just a bonus to have a sweater sent to me, and I’m like, ‘Well, I was going to buy this anyway,’ so that’s really nice.
What’s an underrated brand that our readers should know about for 2025?
I know I’m in a bubble, and brands that I think are well known might not really be as well known. A brand that I do always look at, just because they’re fun, is Call It By Your Name because I found them when I was in Paris. They have a section in Le Bon Marché, and it’s really cool. You could do like toiletry bags, tote bags, and all of that. I think they’re fun. I don’t think they’re underrated, perhaps. I’m sure people know about them, but they’re really fun. Another brand is an Australian brand I love. So it’s probably not underrated in Australia, but I love it. It’s ALEMAIS.
With the social media landscape always evolving, what advice do you have for others who want to create content centered around fashion?
I would say, and it’s the classic answer you’re probably always going to get: to be as authentic as possible when posting and sharing what you want. I see so often people copying another creator, verbatim, using the same templates on Substack, and doing different things like that, and I’m like, this is not how you start. I get that you’re using these people as inspo, but then you’re just like the others. There is a reason that people are following you, and that’s not because you are like the other person that you’re copying. So I would say do it because you enjoy it or it’s your passion or it’s a creative outlet and not to always look to people for inspiration necessarily because then I think you just get caught in that copycat, turning out content that looks like others. And have fun doing it, literally; that’s what everyone says, but making sure you’re enjoying it and respecting those who are also on the platform and your audience as well is so important. I think it is just so easy to tell, for me at least, when people are in it for the wrong reasons, or they’re just not authentic, and I think it comes off, and I don’t know if they realize it comes off that way, but I’m like, this is clear as day. So that’s my biggest tip. And the other thing is what people are usually worried about, like who is seeing their content. They’re like, ‘Oh, these kids from school,’ but that is never something I think about anymore. And once you just get it going, who cares? To me, I don’t even have an audience; I’m just posting into the abyss. Good, someone from high school saw it. Like it. Comment. Engage. So, not to be scared about that as well.
This story first ran in Issue 39: The Digital Issue. Read more from the issue here
