Kat’s Closet Deep Dives: Olivia Jessner, Depop expert

“Kat’s Closet Deep Dives” is a series of interviews with Stanford students about their personal style, where they find inspiration, their views on campus fashion trends and their thoughts on the future of fashion and sustainability. 

In this installment, Kat sat down with Olivia Jessner ’25 to discuss her signature pieces, style and thoughts on sustainability.

This interview has been lightly edited for clarity.

The Stanford Daily [TSD]: In a few words, how would you describe your personal style?

Olivia Jessner [OJ]: That’s a good question. Maybe bright, intentional and coordinated. 

TSD: What are some places you like to shop?

OJ: I think I get most of my clothes from Depop, but other than that, I really like to shop at this brand called Big Bud Press — it’s an LA-based brand. And I also like the website Lisa Says Gah. And then if I have to get something in a pinch, I usually go to Urban Outfitters, but I try to avoid it, honestly.

TSD: What are some of your signature pieces? 

OJ: The color green, grandpa sweaters, statement patterned pants and overalls and jumpsuits — anything of that variety. Those are the four things that I rely on to have a cohesive wardrobe.

TSD: What would you say is your favorite era for fashion??

OJ: I think it’s probably the 90s, but I feel like sometimes the lines blur for me between the 90s and the early 2000s. It’s a mix of the two. I used to be more into the 70s.

TSD: Who are some style icons that you really like from the 90s?

OJ: I really like to look towards girl groups from the time — a lot of album covers. If you look to music, there’s this one song I love called “The Tide is High” by Blondie. And I forget what the that group covered it in the early 2000s was called, but I loved their album cover. I really like to look at what people were wearing at the time, especially Black women — Destiny’s Child, obviously, and also the Pussycat Dolls. And I feel like my other kind of style icon is just grandpas.

TSD: Are there any trends that you really like right now? I know you said you were into Y2K.

OJ: For me, I think the number one trend right now is the resurgence of cargo pants. I absolutely love cargo pants. And I love thrifting old ones, but I also like the new ways that people have been interpreting them, especially with parachute pants and stuff like that. And then, also, the resurgence of Y2K in general — I’ve been a big fan.

TSD: On the flip side, are there any trends you don’t like?

OJ: Honestly, the resurgence of balletcore. I don’t like ballet flats. I can get with some interpretations, like I really liked the Simone Rocha or the Miu Miu ballet flats, with the platform and stuff, but the stuff that’s straight-up what I would wear in, like, middle school — for me, I just think it’s too soon. And in that same vein, skinny jeans as well. And also riding boots. Basically anything I would wear in middle school. I think memories for me are tragedy plus time, and there hasn’t been enough time yet. But I don’t know — those are so polarizing that I always talk to people who really love the trends, and I enjoy seeing peoples’ interpretations of it. But I haven’t hopped on the trend yet.

TSD: What are some of your favorite pieces in your closet right now?

OJ: Every single pair of overalls that I own, I absolutely love. There’s this one sweater that I have that I recently got from Depop — it’s the brand Izod — and it’s between a brown and green, and it’s the perfect type of oversized, and I’ve been wearing it almost every single day since I got it.

It came with this horrible cigarette smell, and I had to get it dry cleaned, and I was like, this is such a nuisance. But when it came back to me, it was just so perfect, I wear it almost every day. And then there are these pants that I got myself over the summer as a birthday present that are from Lisa Says Gah, and they’re called the “Italian Summer” pants, and they have this food on them — a lot of Italian based ingredients. There’s sardine cans on them, which I think is really funny because I would never eat sardines, but I think they’re fun on the pants. Every time I wear those, it’s such a statement piece, and I love it. They just make it an outfit. Also, Ann Ferriday tops on Depop — I have two of those, a green one and a pink one, that I really love. I think they’re also a statement piece.

TSD: How do you like to accessorize?

OJ: I’m actually such a lazy accessorizer, but it looks like I put a lot of effort into it because I wear fifteen or sixteen rings at any given time, but I just never take them off. And I have four or five necklaces that I wear all the time. I like to accessorize with the same jewelry every day, but with very intentional jewelry to where I feel like it can go with any outfit that I wear.

I feel like for me, my rings are my personality. And so I don’t feel like I need to do much else. I really like dangly earrings. If it looks like it could have been purchased at a flea market — it honestly probably was brought to the flea market — that type of jewelry I like.

I really enjoy other types of accessories. For Christmas, I got this secondhand Coach bag from Etsy. It’s just a leather black bag, and I hadn’t been into bags before, but now I really am. I really think it adds to an outfit. And I don’t really do hats that often — my hair just doesn’t agree with that. I’ll do a bandana every now and then if I feel like it, but honestly, I feel like I’m very lazy when it comes to accessorizing.

TSD: What advice would you give to someone who’s just getting into fashion and trying to establish their own style more?

OJ: Honestly, I feel like people say not to take inspiration from other people, but I think it’s totally fine to use other people as a jumping-off point, like asking people what their strategies are. For me, my biggest thing has been curating my Depop. It takes years to do, but brands that you really like, finding shops that you like — all of that curates your page for you. Eventually, the fashion starts coming to you, which is really nice.

I feel like I take inspiration from what’s around me, but I have my core things. I have my four signature  things that I always wear, and I feel like those will always stay with me.

It also really helps you find your personal style when you’re doing it for fun. You have to be excited about it — it shouldn’t be a chore, you know? I just love the prospect of waking up every day and planning a new outfit. During the COVID pandemic — I was class of 2020 in high school — I was really upset because my senior year was canceled. I was bedridden all day, wearing sweatpants. And I remember thinking to myself, one day in April, it had been a month, and I was like, “Let me put on an outfit today.” It really changes your outlook on life, and I feel like it brings me a lot of joy. You can think about the joy that clothes can bring you and use them as an extension of yourself.

TSD: Where do you usually get inspiration for fashion or outfits?

OJ: I do feel like I use social media a lot. One of my favorite things is going on TikTok and just looking — I have a folder on that app of all these outfits. Not ones that I necessarily want to recreate, but of people who I think have really nice style and layering or have put these two colors together, two items together, that I want to try. I feel like I don’t necessarily get pieces from it, but I get styling ideas from it, so social media is big for me.

TSD: What advice would you give to someone who’s trying to shop more sustainably?

OJ: That’s a good question. It can be really hard to shop sustainably because of the price, and honestly, Depop is getting really expensive these days, so I would recommend sites like Vinted or ThredUp or Mercari. Or, honestly, eBay. I love eBay.

Sometimes it’s just about buying less from fast fashion and being more intentional with the pieces that you buy. If I need to buy something that’s fast fashion, I have to make sure that it’s not something I’m only going to use once, and it’s something that I’ve really been wanting for a long time. For me, I feel like the biggest thing is intentionality.

TSD: How would you describe the style profile of campus right now?

OJ: I definitely feel like there are a lot of different vibes on campus. I definitely have noticed a lot of oversized silhouettes, which I love — I do that as well. Low-rise pants definitely are very in right now, and I think all of the different varieties of Converse are in right now. I just got a pair of Chuck 70s, and I’m obsessed with them, so I definitely also participated in that trend. But then I think there’s a lot of people who dress for comfort — I’ve seen a lot of HOKAs around campus lately — so I think there’s multiple camps. But I really like the range that I can see when I walk across campus, and I do think I pull inspiration from people here sometimes.

Olivia Jessner ’25 is a copy-editor at The Daily.

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