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."

When Kit Keenan got out of a Bentley at Pennsylvania's Nemacolin resort on Matt James' season of "The Bachelor" ("the limo was giving me a little bit of a drive-share vibe"), she was inadvertently breaking the show's unofficial but long-established dress code: Instead of a long, beaded, jewel-toned gown, she donned a feathered mini dress with black lace-up heeled boots. From the get, she stood out from the crowd of contestants with her style. 

"I went in there without really knowing what the style code was," she says. "I had watched previous seasons, but while I was packing, I didn't think to bring any long dresses. Literally, every rose ceremony, I was wearing a short dress — I was like, 'Okay, this is very me.'" 

Bachelor Matt James Kit Keenan ABC 2

Now, this was no surprise to viewers that occupy the Venn diagram intersection of Bachelor Nation and the fashion industry (there are quite a few of us!) who recognized Keenan as soon as she made her limo car entrance: She's the daughter of Cynthia Rowley and an influencer in her own right, with her own brand and podcast. She's also still a student, currently working on a degree in fashion and business at NYU. 

To be fair, she was a part of an especially stylish cast of women: Chelsea Vaughn was crowned Best Dressed on night one with her black A'kai Littlejohn gown; Bri Springs' rose ceremony dresses were consistently strong; and Serena Chew's knee-high glitter boots... I mean. Keenan wore a lot of Cynthia Rowley on the show, naturally, as well as other recognizable labels like Off-White, which at times, she remembers, confused some producers: "I was trying to explain to one of the producers — he was like, 'What are those sneakers?' I said they're Off-White, and he was like, 'They're pink.' I was like, 'No, the brand is Off-White. The color isn't off-white."

Keenan's approach to fashion has been shaped by growing up so close to the industry, but when it comes to style inspiration, she's found that looking back in history has been most impactful to her. "I think a lot of times when people have a style icon that's super contemporary, their style is always changing. It's totally fine to follow trends, but it's really inspiring for me to find someone like Jackie O. that I can always reference and know that her style is totally timeless," she says.

Ahead, we talked to Keenan about being an expert-level The RealReal scroller, shopping the Cynthia Rowley sample closet, getting dressed for "Bachelor" dates and more.

"I say that, usually, girls fall into four categories — which is a little simplistic, obviously, there are way more, but — there's the bruh girl, the fairy, the baddie and the hippie. I definitely have fairy style: very feminine, very girly. I love dresses. I love floral print. I say I kind of dress like a grandma. I cannot wait to be that grandma, sitting at a café in a Chanel suit that I bought years ago, drinking a latte and living my best life. That is, I think, my ideal style, an old grandma.

"I definitely went through the more rebellious high school style, where I was obsessed with American Apparel pleated tennis skirts. I was always breaking the dress code at my high school. I went to Grace Church in New York, which, at the time that I started, was very 'Gossip Girl' in the sense that they wanted us to all dress pretty modestly, and I was definitely not about that. I really found my style later, in college. 

"Growing up in New York City, style was so important [to] everyone I was around. All of my friends had their own cool styles; even in middle school and in high school, what you were wearing to school was so important. It was definitely a status symbol, but also a way to set yourself apart. All the cool kids wore Undercover and brands that no one had heard of at the time. That was always a part of the zeitgeist. But then also, I was always around fashion because my mom is a designer, and I grew up around people that worked in the industry and going to fashion shows, where people had the craziest outfits and were always telling me about cool small brands and designers coming up in the city. That was another level of seeing what the industry was all about.

"Most people my age get their fashion inspiration from Instagram and TikTok. That's where I follow a bunch of my friends and influencers [whose style I love]. It's cool because you can see people from all over the world and how they're dressing. One of my closest friends, Ella Rose, has the cutest style; it's very fairy. I would say Hannah G., I love her style also — 'Bachelor' squad. I also love Lilah Ramzi; she's a Vogue editor and is always posting her vintage looks and they're insane. I don't know where she goes vintage shopping. I'm always like, 'Lilah, please take me with you next time you go.' I love following Serena [Chew], because she knows all of the cool young Instagram brands. She's definitely a baddie, by the way. Our styles are different, but I love following her; sometimes I'll wear a top or something that's a little bit out of my comfort zone or shows a little skin and I'm like, 'Okay this is my inner Serena.' A lot of my friends from the show actually moved to New York, and I love to see how they're getting inspiration and stuff in the city. I try to mostly look on Pinterest for style inspo, content inspo and life inspo... It's so curated to your personal style that it's kind of nice. I'm just served old Dior, old runways and vintage photos.

"At the same time, [social media] can kind of become a little bit of an echo chamber where you know these three influencers all have a very similar style and all post very similar things, and that's cool, but at the end of the day, I like looking back in history for style inspiration. Because I know that's an icon that's not going to change as much. I want my personal style to be more timeless, rather than based on trends. Jackie O. is my ideal style icon. I love her. Princess Diana, I love her style as well.

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"I'm studying fashion and business at Gallatin, and I've learned so much about the ethical and sustainable issues within the industry. Growing up, I saw my mom dealing with the very stressful business side of fashion, but I didn't really know as much about the sustainability issues as far as manufacturing and stuff like that. I've been learning about that for the past three years, and it has definitely made me look at fashion completely differently. I always thought when I was done with school, I wanted to work in fashion, but [now] I'm more interested in working in sustainable fashion, if I were to do that, or on the business or publishing side. It can get very emotionally taxing to work in an industry that you know more products mean more suffering for the people working to create those products and for the environment. That can get morally icky.

"I'm the biggest scroller on The RealReal. I will spend hours on The RealReal. I think shopping secondhand is amazing. I remember one time, my mom was accepting an award from SCAD and the woman who was presenting it to her was wearing these Cynthia Rowley leggings she had gotten off of The RealReal. This was early days, when I think designers were a little like, 'Hmmm, I don't know if I love that.' But I remember my mom [being] so happy, because it showed that this pair of leggings was so loved that one person could wear them and have a story in them and then this woman could wear them and present in them and be so confident in them. That's such a beautiful aspect of the fashion industry, that the cycle will never stop. Clothes are so much a part of our personal identities. The fashion industry is huge, but finding better ways to consume and consuming less is all we can do right now; also, still appreciating the beauty and self-confidence that comes from wearing an outfit you love.

"I love estate sales. Estate sales are the best. I love Depop, What Goes Around Comes Around. For my day-to-day, I love Reformation and shopping on sites like Ssense, Net-A-Porter and Revolve — places where I can discover new brands. I'm pretty lucky, because with my mom... I can fill in the gaps there as well. [I always take Cynthia Rowley's] little short dresses. Especially in the summer, that's all I wear. It's a trick, because people think you have it all together when you're wearing a dress, yet it's the easiest piece to put on. Little short dresses are definitely my go-to, which is why I also love Reformation. So easy with sneakers, or dressed up with heels for dinner. 

"EB Denim sent me a pair of jeans — it's kind of like Redone — and they look so cool. They elevate the denim to a whole other level. I wear them all the time, with a cute little Brandy tank top or a great blouse for dinner with heels. I actually splurged on a pair of vintage Levi's; sometimes they can be really expensive, but once you find a pair of vintage jeans that fit like a glove, it's the best. They're so hard to find, and you might have to go somewhere and try on a million different pairs. I found my last pair at The Vintage Twin and was just like, 'You know what? I'm gonna spend some money on these,' because I know that finding a pair of vintage jeans is so hard and when it happens, it's literally like trying on a wedding dress. It's insane.

"During the day, [I'm] usually in sneakers because I'm running around the city. I try to walk everywhere. But I love little kitten heels. My feet are still getting used to walking around in high heels — they don't know what those foreign objects are. I just found this brand Alohas, which is amazing. Steve Madden is awesome, honestly. I found the cutest Chanel kitten heels slingback shoes on The RealReal and I have worn them to death.

"The first designer piece that I bought for myself was a Chanel flap bag. I wear it every single day. It's absolutely destroyed at this point because I wear it so much, but I know I'll have it forever. I got it off The RealReal, again. It's one of those pieces that's going to last forever. That's the great thing about investment pieces: They help dress up every outfit. For jewelry, I just got a few pieces from KBH Jewels; I love Verlas as well. 

"I actually found out about ['The Bachelor'] kind of late to the game, so I really didn't have time to prepare. I had probably like four days. Most of the stuff was my mom's — which, so thankful, and I was happy that I got to rep her brand. I got two of my best friends, one who has worked for my mom for years and another who works for Louis Vuitton, to come over, pick looks and take photos of me in everything. I definitely didn’t pack enough. I got there with two suitcases, and I remember girls coming with four giant things. I was like, 'Uh oh, I don't have enough stuff.' 

Bachelor Matt James Kit Keenan ABC

"Throughout the process, I had my mom send me boxes of clothes to wear. Thank gosh I have her to fill in the gaps that I missed, because I literally didn't bring any jackets or warm clothes. I was definitely unprepared in some areas. But you only realize when you get there that you don't know what you're doing every day.

"There was one date where we were walking through the forest — I didn't know what we were doing until we got there, and I was wearing a pair of trousers that I had gotten at an estate sale, these beautiful vintage Saint Laurent trousers, and heeled boots. And they were like, 'Mm, I think you gotta change. This is gonna be little bit more involved today.' Thank gosh I had jeans. That was definitely not the move. 

"My friend that helped me get ready for the show, Devon, she's like a fashion protégé — she just knows everything. I will ask her [for her opinion]. You need to have somebody who at least follows the sales and stuff like that, especially for high designer and high fashion. Everyone needs a friends that knows what's in at the moment."

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