Sound Off with Stylist, Educator, & Speaker Rachel J
In the latest episode of the Dailey Blend, we sit down with Rachel J., a renowned stylist based in Chicago, to delve into her fascinating journey from the world of advertising to becoming a global fashion stylist. Rachel shares her story, insights into the fashion industry, and how technology has revolutionized her business.
Rachel's journey into fashion wasn't straightforward. With a background in advertising and journalism from the University of Illinois at Urbana Champaign, she initially carved out a successful career in corporate America. However, her true passion lay elsewhere. "I just wasn't passionate about it. I couldn't imagine doing that for the rest of my life," she recalls. This realization led her to pivot into the fashion industry, starting at a boutique in Hinsdale and eventually working for Nordstrom in Los Angeles.
In 2013, Rachel took a leap of faith and launched Rachel J. Styling, a decision she describes as the best of her life. Over the years, she has witnessed significant shifts in the fashion landscape. "The biggest thing from 2013 to now is how people embrace working with a professional stylist," she notes. The rise of online shopping and the influence of social media have transformed how people approach fashion, making personal styling more accessible to the everyday person.
One of the most compelling aspects of Rachel's business is her ability to blend in-person and virtual styling. The COVID-19 pandemic posed a significant challenge but highlighted the potential of virtual consultations. Rachel adapted by offering curated boxes of clothing to clients and guiding them through styling sessions over Zoom. "I'm forever grateful for Zoom and this platform," she says, emphasizing the importance of technology in keeping her business afloat.
Rachel also touches on the importance of building a team and the challenges of letting go as a solopreneur. "We need to learn how to let go," she advises, stressing the value of finding team members who complement your skills and share your work ethic.
Looking ahead, Rachel is optimistic about the future of fashion, particularly in Chicago. "It's a very supportive, uplifting community here in Chicago," she says, highlighting the city's burgeoning fashion scene. She also sees tremendous growth potential in the personal styling industry, encouraging aspiring stylists to hone their craft and develop their businesses.
Those interested in following Rachel's journey or seeking her styling services can find her on Instagram, LinkedIn, and her website, Rachel J. Styling. Tune in to the full episode for more insights and inspiration from this dynamic fashion entrepreneur. Don't miss out on this engaging conversation with Rachel J. Listen to the episode now and discover the world of personal styling from one of the best in the business.
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Transcription - Sound Off
Host Reed Dailey (@ReedDailey): This is the weekly rundown segment of the Daily Blend Show
The Dailey Blend features owner-operators, entrepreneurs, movers and shakers
>> Reed Dailey: Hey, everyone.
>> Reed Dailey: Welcome back to the Dailey Blend, a show with me that is reed Dailey. If you are new here, this is the sound-off segment where we feature owner-operators, entrepreneurs, movers, and shakers. Just people doing great, fantastic, and exciting things. I am thrilled to have the opportunity to showcase my conversation with Chicago's own Rachel J. My favorite stylist in the whole world, someone I've known for ten plus years, and really, dive into her role as an owner operator and the world of, virtual and in person global styling and what it's like to interact with customers in real life, online, all day, every day, and keeping up with trends using the latest, latest and greatest tech. Run into a team and so much more. As always, you can check out this show on Apple Podcast, Spotify, Google Podcast, and YouTube. You can check out the full show notes on Dailey Blend, and you can check out Rachel on Instagram and her own website. Rachel J. I will put all of those links in, in the show notes and on Dailey Blend. With all that said, let's jump into our conversation.
Rachel J. is a personal stylist and entrepreneur.
>> Reed Dailey: Hey, everyone. Welcome back. We have Rachel J. on the Sound Off podcast. We're going to be talking about all things entrepreneur, fashion, and personal stylist. So, Rachel, why don't you just tell us where Zoom finds you?
>> Rachel J.: I am right now in Elmhurst, Illinois. I'm right outside Chicago in the western suburbs. Rachel J. Styling is based in Chicago, but I work with clients all over the world. That's really the beauty of virtual work.
>> Reed Dailey: Yeah. So, let's just jump into it
Rachel J. Smith started as a personal stylist in 2013
So, I know you from styling me ten years ago. That's how we met, through what I think was a startup company. But your journey has moved in and around various brands, and working as an individual stylist. So maybe give us a little background of, like, how did you get into being a personal stylist? And, you know, what was that like?
>> Rachel J.: Yeah. So let me take it back a bit to paint the picture of my story and how I got into fashion, because it was not always this way. I actually went to the University of Illinois at Urbana Champaign. I got my degree in advertising with a minor in journalism. So, you know, I'm the daughter of immigrant parents from the Philippines, and even advertising and journalism was a stretch for them. Like, they didn't know what the heck that meant. you know, my mom's a nurse, dad's an engineer. Very traditional filipino family. And, so if I had told them back in my college days that I wanted to go into fashion, no way. There's no way they would drop a dime on me going into fashion back then, which actually served me well. I went into corporate America, worked in the advertising agency for seven years. and while it was great, it was lucrative. I was doing well. Bought my first condo and car when in my twenties. I just wasn't passionate about it. I couldn't imagine doing that for the rest of my life. So I knew that I wanted to get into fashion. And at the time, I thought, I really want to open up a boutique. I guess maybe many fashionistas at some point in life have thought I'd love to open up a boutique. So I pivoted out of advertising and started working in Hinsdale, at a boutique. And it happened that the owner needed a manager and needed someone to help with the buying and running of the shop. And so I started in fashion there. And that was kind of where I figured out while I was on the floor and working with clients in Hinsdale, that what I really loved about fashion was learning about the designers and then learning how to dress both men and women for all the occasions and events of their life. so that's kind of where it blossomed. And then the journey took me to Los Angeles. I, worked for Nordstrom a little bit, actually for, it was about three years. And so I worked in one of their designer divisions and then managed their wedding suite. but I think at the core of it, I always knew at some point I still had that very entrepreneurial spirit and I wanted to have my own baby, my own business that I could watch grow. And so I did it, 2013, February of 2013 is when I started Rachel J. Styling. And I had never looked back. The best decision of my life.
>> Reed Dailey: So during that kind of time period, from 2013 to now, a lot has changed. economically, styling for what people love, what do they want to wear at the office in the in between phase, and then casually, you also had, crazy technology changes.
People now embrace working with a professional stylist, um, in a way
So talk to me a little bit about, like, you know, how have things differed from when you first started and what they are now in terms of the way that you kind of run your business, and think about interacting with customers.
>> Rachel J.: Yeah, well, I think the biggest thing from 2013, ah, to now is how people embrace working with a professional stylist, in a way that wasn't really available to them in the past. When I started my business in 2013, having a stylist really wasn't for the everyday person, right in the way that I wanted to work with them. You could go to a department store or any of the stores, but you felt very limited, like you had to buy what was at the store. And obviously the salespeople there and the stylists there, they have quotas to meet. So it's different than working with an independent stylist who can curate and has partnerships with all these different designers and shops. so I think, one, the mentality about working with a personal stylist has changed. Whereas now they're like, wait a second. Personal styling is like, if you want to improve your image and your look, who do you go to? If I wanted to get stronger and more fit, I go to a personal trainer. If I wanted someone to help me with my diet and figure out what I should be eating, I'm going to go to a dietitian. So now, fashion has professionals. We, as personal stylists, obviously know a lot about dressing different body shapes and working in different industries and working with all different ages and backgrounds. So, that has changed. But I think, also the way that people shop is different, a lot different than what it was back in 2013. more people were shopping in person back then. And then over time, obviously, over the past decade, there's just been an explosion of online shopping, influencer shopping from social media. the way that people kind of look at style and what to buy, is different than it was ten years ago.
>> Reed Dailey: And do you find, like, we've seen more individuality where there are sort of pockets, or do you find that customers have sort of moved towards everything's more of the same and kind of similar looks, but just maybe low, medium and high? You know, what are you seeing in terms of where the market's headed? And is there a difference between men and women in that regard?
>> Rachel J.: Oh, that's a good question. so I think that what you're kind of getting at is, is there kind of a uniform way?
>> Reed Dailey: Yeah. Better said than me?
>> Rachel J.: Well, yeah, and I see that now. This also depends, obviously, on age. So I style anyone from teenage kids all the way up to grandparents. So the trend, of course, for the younger generation, I would say, like, around high school, maybe a little bit of college, but mostly high school, is they just want to fit in to this cookie cutter kind of look and way and having all the same brands and having the same aesthetic. And that's okay, because I think when you're young, you're just figuring out who you are and kind of what you gravitate towards and what you love and what you don't love and things like that. So that's fine, I see that. But when you get into, you know, you're more mature, you're starting in your professional life, that too. I feel like starting; you just kind of want to, I don't want to make too much noise; you just want to Blend in a little bit. But as you move through your career and you mature and get older, I think there is a trend to wanting to stand out a little bit more or put together looks more thoughtfully. but it does just depend on the mindset of that person. It doesn't matter whether it's a man or whether it's a woman. It depends on if that person really believes and understands that the way that they dress and the way that they put things together, is a reflection of what's going on on the inside, how they feel about themselves, how they think about life. so it's just, it's a reflection. What's on the outside is reflecting what's on the inside.
>> Reed Dailey: Yeah, gotcha.
There's still a lot of gray area in terms of working with an independent stylist
So maybe talk to me a little bit about, you know, when a customer comes to you or someone, a prospect, I should say, comes to you for the first time and says, you know, I recognize that there is a chain I need to change, but I've not ever worked with a, ah, personal stylist and probably, you know, a little bit, uncertain in terms of the process. How do you navigate a first-time consumer of services that you provide, and what is sort of like the coaching you give them in terms of here's how we're going to work together and here's how we're going to be successful together?
>> Rachel J.: Yeah, that's a great question. There's still a lot of gray area in terms of the process of working with an independent personal stylist. So it's rare to everybody, they don't know what we do. So I think that it's on us to really walk them through the process from beginning to end. So the very first thing would be a consultation. And this happens in obviously many different industries, but of course when you're working with a stylist, that first introductory call, 2030 minutes to sit down and actually talk through, what are you frustrated with? what are the struggles that you have getting dressed and then what do you want to achieve? What is it that you are hoping through. Working with a stylist is going to transform in your life, whether that is your overall look or just the ease of getting dressed. We've got a million things to do. A lot of the clients that I work with are coming to me when they're frustrated. They don't have any time, but they want to look really good. How do you do that as a stylist? I know all the different designers and I know all the shops kind of how to pair things together quickly. But for someone that is very clueless about that, they want to have a professional just kind of take it off their hands so it's not so overwhelming. So that first step would be, an introductory call. And it's really the first time for many of my clients that they're actually verbalizing their style. And I'm asking them, you know, tell me about your lifestyle. Tell me what you do Monday through Friday. What do you do on the weekends? What do you do in the evening? So it's my job as a stylist to figure out what they're doing in their lives and then me putting myself in their shoes, knowing how they want to move and navigate through this world, what's going to work on their bodies. I'm just asking a bunch of questions. We really need to be, investigators and curious about, you know, what it is that they already, like, figure out, you know, colors that they like, patterns that they like, and just, just what it is that they really want to accomplish in the end. So, and then after that introductory call, we kind of assess where we need to start. And every client's different. For me, I don't have, like, a standard. You know, this is the package, and I, you have to go through steps a, b, c, d. for me, I'm going to meet them where they're at. So if a client already has a good, good wardrobe, there's many clients out there. They like to shop. They know what they want, but they just don't know how to put it together. So that's one service. Or there's some clients that just want to start from scratch. Like, they can't stand what's in their closet. They need to get rid of everything. And let's start from the beginning. yeah. So it's really discovery of where they are and then where they need to go.
>> Reed Dailey: Gotcha. So it could be almost like fine tuning, refinement, versus sort of starting from scratch. Yeah. And then what? in terms of, like, prepping for this call.
Rachel J. says assembling a team came from letting go as an entrepreneur
we talked about you assembling a team, and we talked about the fact that when you first started this, you were a solo entrepreneur. how has you being a solo entrepreneur to now having a team underneath you evolved? What was that process for you in terms of recognizing that, hey, I've hit certain threshold, and I need to bring people around me in terms of capability, extensions, or supporting. How did you decide that as, an entrepreneur?
>> Rachel J.: I think as a solopreneur, we need to learn how to let go. And because we are the multitaskers, we are the doers of everything. But it is impossible, almost impossible, to grow to where you want to be and, you know, burning yourself out doing everything. so I think a lot of solopreneurs have to trust that one. You're not going to find someone to do your work exactly like you. I'm not trying to find that, but I'm trying to find, you know, someone who compliments or someone who has the same work ethic, same, hustle, same. Doesn't have to be the exact same vision, right. Because as especially in the creative, creative arts world, right. I, appreciate all the different, perspectives and visions of my stylists. and I really, welcome it, you know, as I'm getting older, the stylists that are all, you know, working on my team, they're younger than me, they have a fresh perspective, and I never want to belittle that because they're, they're younger. I welcome, that, and I think that, ah, as a business owner, you need to, you know, understand kind of everyone's in a different stage of life, and there's beauty in that. There's beauty in the fact that she may be 25, but, you know, she can assist me with a 50 year old client and give her a different perspective than me. so I think that, you know, assembling a team came from a lot of letting go. And I still struggle to find, stylists that I would trust to go out on sessions without me. You know, I feel like I'm starting to get to that point, but I still feel like I need to be there or involved in the process to a certain degree. And that's what the clients want, too, right? So they're, they're expecting to work with, with Rachel J. And if they don't, it's, you know, at least I have some part of the, of the process. but I can say this is, this is also something that I've done. I've had. I've hired interns in the past, and I hired two interns, this past, this past year, starting in January. If you're not prepared as a manager, a business owner, to actually delegate work to interns, it can become a big missed, ah, opportunity. So we as leaders, we as the managers, we have to be prepared with the workflow. Like, what are we actually giving them? Because they can't read our minds. You know, I try to meet with them every week so that they, can hear from me and they can kind of, we can stay on the same page. But I think if you're managing people and you don't have a plan for them, it's really hard to actually accomplish anything.
>> Reed Dailey: I mean, everything you've just described in terms of going from your work with clients to how you're thinking about, I will call it defining needs and delegating or plan, do review exactly the same framework that I see in a lot of the consulting projects I do, which is totally refreshing.
You use technology to amplify your brand on social media and your website
talk to me a little bit about, you know, before we got on, we talked about, you know, your TED talk and, and having a videographer and using technology, and you're super, pervasive in terms of the amount of content you put out on social media and on your own website. How have you used the power of technology to amplify, and communicate your brand? How has that evolved and what are the folks and capabilities you've activated to do that?
>> Rachel J.: I think from the very beginning of my business, I'm very fortunate to have a photographer and videographer who has kind of been by my side through everything, capturing this whole journey with me. I don't know if that's kind of along the lines of technology is what you're talking about.
>> Reed Dailey: Yeah, absolutely.
>> Rachel J.: Absolutely. Okay. but without her capturing the images, the behind the scenes, what showing me at, you know, capturing me actually doing the work and then sharing that, publicly on, you know, on social media or in newsletters or, you know, on the website without that content. I feel like entrepreneurs really struggle because, especially when you are small business and you're trying to just get people to notice that you're doing the things that you're doing, without having that visual, content, it's a struggle to really get people to trust your brand. And so I think that that's probably the biggest part, for me, especially because I'm very involved in Instagram. That's probably my number one source of getting, the word out. It's where I'm most active I'm also active on LinkedIn. Not as much on Facebook, but I still have my page up there as well. but it's incredible how many clients I've gotten through Instagram or just developed a following of really engaged, people that are interested in what I do. I think that m the base of my following on Instagram is very diverse. And that's another thing that I think has, been really helpful in terms of the videos and photos and everything is just kind of showing all the different aspects of how I work and what I do.
>> Reed Dailey: Do you think putting a little bit of behind the scenes, like, kind of not only just shows people, like, brings them on the journey, but kind of maybe, like, humanizes the work? Is that kind of 100%?
>> Rachel J.: 100%. So I teach, obviously, I've taught the business of personal styling. I wrote an online course, and then I teach at Columbia. And so I have fashion styling students where I'm not only teaching them the foundations of styling, but also the business part. And I'm constantly reminding them to take behind the scenes because your audience wants to. They don't know what you do. They really don't. They don't know the process of your work and kind of the hustle, the hustle behind it. Right. You can post fancy photos of the end product, but if you don't show the photos and the video, the little snippets of, the grind leading up to that, it's not as meaningful. Right. Perfect example is, you know, the TED talk, and that's not styling work. Right. But leading up to the TED talk, I was in Tulum, I was writing, I was coming up with, you know, finding the outfit, and it just brings people in. There's so many angles where you can bring people into your story. and just obviously that branding is a whole other part of this, but the people that I work with want to work with me because they connect with me. They trust that I'm a good stylist. Right. But at the core of it, in any business relationship, you want to work with good people that you, you know, that you might want to become friends with, you know, and that's a beautiful thing.
>> Reed Dailey: So, interesting.
In ten years since you started your company, technology has changed dramatically
I want to ask one more sort of technology question, before we talk about kind of market trends. So, you know, in the ten years since you sort of started in eleven, I guess technology has evolved. And how have you found, when we kicked off this conversation, you mentioned you've got customers in the Chicagoland area, but across the country. How has the interaction with customers changed. Do you find that they're email, phone calls, like, you know, everyone's different. Like, walk me through how technology has helped or hurt or changed the way that you've interacted with your customer base helped, immensely.
>> Rachel J.: So Covid happened 2020 and no people could care less about what they were wearing. It was the time in fashion where everyone was going into sweat suits and jogger pants and comfies at home. And for me, I was at that time, I was, what, seven years into the business and I thought, I'm going to have to think of something else because nobody cared. But, coming out of COVID there was this resurrection of people really caring about how they're going to show up now. They're like, oh, shoot, I'm going to go into the office two to three days a week. I better show up. So, that being said, during the time that Covid was happening, technology in terms of doing Zoom calls and still working with clients around the world, with virtual styling, truly virtual styling. So it wasn't just a consultation, but I would have, I'm gonna use a client in LA, for example. I would have boxes sent over to the client, curated by me. I would work with the designers and the shops and I would send boxes to my client in LA, give enough lead time for her to receive the boxes. And then we would, we met over Zoom. And so she was literally like, you know, changing, going into the outfits and I was directing her on, what to put together. And it's, nothing's going to ever replace being in person and having me, you know, touch and feel the fabric and do all the tucking and the zhuzhing and all that stuff, nothing's going to ever change that. But the fact that we could, work over Zoom and she was, you know, how many miles away? 2000 miles away, and I was here. And the end product, she was still, like, very happy with all the looks and she got great new outfits and, and felt good after that. I'm forever grateful for Zoom and this platform. Whatever. Google Meets Google, all the things. It's amazing. Nice.
Chicago fashion is on fire right now
>> Reed Dailey: yeah, no one has a crystal ball, but you've obviously, between teaching at Columbia, having your own, online course, and then obviously working with your customers, where do you see fashion heading and where do you see styling world heading and supporting of people trying to connect and figure out their own personal brand and kind of enhancing their look and feel.
>> Rachel J.: Yeah. Gosh. Looking to the future, in fashion, I feel so blessed and honored to be in fashion at this point, because it's such a good time to be here, especially in Chicago. If you are in the Chicago fashion community right now, you know that it just feels like it's on fire. Like, everyone really, the community is there. People want to get together and connect from, whether it's designers, stylists, influencers, shops, etcetera. Like, it's a very supportive, I feel like a very supportive, uplifting community here in Chicago. So, we're doing it. We're never going to be New York. We're never going to be Paris or Milan. But, in terms of Chicago being, a place where people are like, oh, the fashion in Chicago is really, shown out, and everyone's intentional and making an effort. Whereas I feel like in the past, in Chicago, it was that city where people were just, again, Blending in, just wanting to get by and not really, make a mark or stand out. But I feel like fashion in Chicago is, people are more bold. They're bolder than they've ever been. which is a great thing in terms of the industry as a whole. I feel like there is so much opportunity in the personal styling, business. There's not enough of me. There's not enough of me to take care of all of the, everyone's out there in every industry of every age group. And so I'm a champion for all stylists. I feel like, come on in and learn to learn your craft, learn the art of styling, and develop a business, because people really do need help. You know, there was kind of when I, there was a time when I thought, people know how to put outfits together. People know how to put a, shirt and pants and a dress together. No, it's not second nature to everybody. To some people, it's more so that. But for a lot of people out there, they need help. And so I am encouraged that the styling industry is growing, and I hope to see more stylists in this space.
>> Reed Dailey: Yeah, very cool. close us out. Tell us where we can find you on the web and online.
>> Rachel J.: You can find me online at racheljstyling.com. so, Rachel, just with an racheljstyling.com, most active on Instagram @racheljstyling. So racheljstyling.com there, and also on Facebook - @racheljstyling, you can find me on TikTok, but I'm still getting there. I'm still trying to build that up, or it's just amount of how much time you, put into it. So I'm not very active there. But then on LinkedIn, I love to see people connect, with me there. So, Rachel Jimenez Penca. And, yeah, I'm at all the places.
>> Reed Dailey: Perfect. And for all the show, all, the links, we'll make sure we put those in the show notes so you guys can find them. Rachel, thanks for joining us, and, thanks for, you know, helping people in the Chicago land and throughout the world, you know, look better and feel better. Appreciate you being on.
>> Rachel J.: Thanks so much for having me.
Rachel J. talks to The Dailey Blend about being an owner-operator
>> Reed Dailey: All right, that wraps up our conversation with Rachel J. Once again, I just want to say thanks to Rachel for spending time and talking to us about what it's like to be an owner-operator. What's it like to run the team? What's it like to be in fashion in 2024 and so much more? As a reminder, you can go and connect with her on Instagram and check out her webpage. Rachel J. I've got all the show notes in the details. And over at Dailey Blend, don't forget to like, follow, and subscribe to the show on Apple Podcasts, Spotify, and YouTube. You know the drill.
>> Reed Dailey: Check us out on social media.
>> Reed Dailey: Social at Dailey Blend on X and ig, as well as threads. And with all that said, catch you on the next episode of, the Dailey Blend Show.
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