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How I Shop: Eileen Kelly, Also Known as @killerandasweetthang

The sex educator and influencer gets personal about how mood and memory influence her shopping choices.
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Eileen Kelly. Photo: Eric White/Courtesy of Eileen Kelly

Eileen Kelly. Photo: Eric White/Courtesy of Eileen Kelly

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

For sex educator and influencer Eileen Kelly, shopping and style go hand in hand with mood and memory, whether she's using clothes to celebrate the memory of her beloved mother or also tapping into the nostalgia of different eras. To that end, you can often find her wearing one of her mother's patterned frocks paired with a vintage Fendi Baguette bag at fashion week events or one of her various speaking engagements where she likes to get real about what's lacking in today's sex education.

As someone whose life has been scrutinized by the media, Kelly is is not afraid to get personal about the ways buying things — whether it's scrunchies, toothpaste or kids' Nike sneakers — can, at times, fill certain voids. Not that there's any shame in that; many of us are guilty of this type of behavior, too.

Also like many of us, Kelly has trouble parting with items that hold any sort of meaning. And as the founder of Killer and a Sweet Thang, a site that publishes young people's stories about love and sex in the digital age, she's a firm believer in sex- and body-positivity. To her, lingerie represents something deeper, whether you're wearing it under your clothes for a night out on the town, going to sleep alone or for an Instagram snap.

Here, Kelly fills us in on her earliest shopping memories, where she finds her favorite vintage pieces and why she travels with 50 pairs of underwear.

"When I was younger, I had no neutral clothes. No black. Nothing. I only wore crazy colors, probably until middle school. My memories are really spotty but I used to shop at this place called Oilily, it's a brand that went bankrupt around 10 years ago. I think I heard that it's back now, but switched owners a few times. They made these eccentric, colorful patterned children's clothes that were meant to be worn together. I used to have these brown Dr. Martens boots from there but they were covered in flowers and I would wear them with a patterned skirt and a T-shirt that had a million different flowers. Their patterns were so over the top.

I would describe my style now as casual and comfortable but it also totally changes with my mood and what's going on in my life. I also like to keep a certain feminine element to whatever I wear. Recently, I just have way too many clothes and don't need so much stuff anymore. And then on top of that I get sent so much stuff from brands. It's actually insane how much stuff I get sent. I'm wearing jeans right now that someone gave me a week ago. I haven't bought jeans in three years because I just get free jeans all the time.

I like to shop secondhand luxury for shirts, skirts and dresses. I shop online a lot, on sites like Vestiaire Collective, The Real Real and 1st Dibs. I also like to go to a few little vintage stores in Brooklyn but I don't remember their names. I have stuff from all different eras. It's really depending on my mood. For example, I have all these really beautiful skirts and stuff from the 1920s and '40s. A lot of the stuff I've been wearing recently is from the early 2000s.

I have all of my mom's clothes from early 2000s. I don't really have any distinct memories of her. So this feels like a way I can connect with her memory and aura. It's really special to me to be able to fit into her clothes and wear them. She had a wild, eccentric style, which is probably why I dressed so eccentric when I was little. She used to pair everything together — a lot of animal print, some bright colors — but I dress slightly more minimal.

Her clothes feel like a piece of my personal history that I can wear on my body. And that's really shaped my personal connection with fashion in general. It can be so much more than just throwing something on the morning.

I'm a huge body positivity, sex positivity advocate. At night I'll wear different lacy and fun underwear, but for my everyday outfits, the underwear that I like to sleep in it are cotton briefs that I buy from the Gap. I feel like wearing lingerie is such a great way to feel comfortable in your own skin. I don't wear it for other people. I like to wear it for myself and know that it's underneath my clothes when I'm out to dinner. Recently, I've been sleeping in these cute, vintage slip dresses. They're vintage Victoria's Secret from the early 2000s that I got on Ebay for super cheap. They're really comfortable.

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There's this bra I'm obsessed with. It's by a brand called Cuup. I'm actually wearing it right now. They sent me a few. This is not sponsored; they just gave them to me and I'm obsessed. I wear them every day. They're like the best everyday bra.

Whenever I go somewhere, I travel with like 50 pairs of underwear. Everyone thinks I'm crazy when they look at how many pairs of underwear I bring, but I'm a woman with an agenda, discharge and a full life. If I end up going swimming, I don't want to put on dirty underwear, you know? I just feel more safe. Even if I'm going for a sleepover, I'm bringing an extra pair of underwear.

I have this suitcase I use when I travel, it's actually called Raden. It's this little tech suitcase. It's actually discontinued now, but you can still find them for really cheap. It's a carry-on and you can fit so much stuff into it. I'm dressed for comfort on flights always, so I'm usually wearing pants. I don't give a fuck what I look like and I'm not trying to dress to impress, to be honest.

I'm really lazy about trying things on in a store. I'll usually just buy them and then I'll make the trip to return if I have to. I'm a firm believer that you can dress really well, have amazing style and not spend a lot of money. I'll spend money on specific pieces once a year or a few vintage pieces here and there, but I'm definitely not someone who walks over to Barneys regularly and drops a lot of money on a new design. I'm also very straightforward with myself with knowing what is is just fully out of my budget. I love buying purses, that's usually what I splurge on when going shopping.

I like small handbags. I don't really have any big bags. You will never catch me walking around with a big bag, unless I have my laptop with me. I like tiny bags that just fit my wallet, my keys and my phone. My favorite bag is the Fendi Baguette bag, which was really popular in the late 90s, early 2000s. Sometimes I'll find them for really cheap online. I have them in a bunch of colors. That's my favorite go-to bag.

I definitely have some fast fashion in my closet from places such as Topshop and Forever 21. While ethically I don't agree with the conditions that a lot of fast-fashion clothes are made in, at the same time, I believe that regardless of your financial situation, you should be able to feel fashionable and have access to the designs that are popular and cool at the moment.

Shoe-wise, I love my Nike Air Force Ones. I have 20 pairs. They are my go-to sneaker. I go through these periods where I'm really obsessed with one thing and I'll only buy or wear that. I fit into the children's sizes so they have a lot more color options. I buy them on Ebay for really cheap, so I have them in all these different colors. They are a fun way to break up an outfit and add a pop of color. They're such a classic shoe. As far as my other shoes, I'm really obsessed with these little ballet slippers with a tiny heel in patent leather. I wear those to dinner all the time and you can dress them up or down. They're just a really versatile shoe.

I'll usually only buy something major once in awhile. Every six months, I'll need something specific. For example, I needed a warm coat this year so I bought it at Aritizia. For Christmas, I asked for a hat.

I've always treated my relationship with clothing and shopping as if it's a band-aid solution. If I'm in a good mood, I will be like, 'Oh, I don't need anything right now.' But when I'm really upset. I'm like, 'Okay, I need to buy something.' The instant gratification thing is real. I mean I could even get the rush of purchasing something from buying scrunchies and toothpaste, so it doesn't really have to be like a huge item.

Living in New York is really dangerous because you're walking by a million stores every second of your life. Yesterday, I was walking in Little Italy — thank god I wasn't in a funk; I was in a good mood — but I saw this thing in the window. It was a little cosmetic bag and it said 'Crazy Cat Lady' on it and I could feel it pulling me into the store, but I walked away.

When I was younger, I used to be a hoarder, which is definitely related to my childhood trauma. But yeah, I have a hard time getting rid of things. If I have a memory attached to something, it's really difficult for me to donate it or give it away even if I never wear it. I still have this dress that I was wearing when I met one of my ex-boyfriends from five years ago and I'll probably keep it for forever. Weird stuff like that, you know? Or the T-shirts that I bought when I first went to college, but they're too small and got ruined in the wash."

This interview has been edited and condensed for clarity.

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