Intuitive Style
Intuitive Style
Learning how to listen to ourselves, with Dacy Gillespie
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Learning how to listen to ourselves, with Dacy Gillespie

The first ever episode!

You’re listening to the first episode of Intuitive Style!

Hosted by

.

I’m so delighted to have

as our first guest on Intuitive Style. I seriously couldn’t think of anyone better to help me introduce the concept of this podcast. Each episode offers practical tools and real-world examples to help you quiet external noise, trust your instincts, and create a wardrobe that helps you feel comfortable, confident, and truly yourself.


Episode Transcript

Welcome

Hello and welcome to the first episode of Intuitive Style. I'm your host, Maureen. Together, we'll explore the connection between mindfulness and personal style. We're all searching for a personal style, but what if it's been within us all along and we just haven't learned how to listen? Today's guest is all about teaching us how to listen to our intuition.

is an anti-diet stylist, author of one of Substack’s top personal style newsletters and all around cool person. Please enjoy this conversation.


Maureen

Hi, Dacy How are you?

Dacy

Thank you so much for having me. It's good so far.

Maureen

Great. I'm so excited to talk with you today. I know there's so much overlap between the kinds of things that we're doing online and just really excited to sit down and talk with you today. Just to get us started, could you just really quickly say your first and last name and your pronouns?

Dacy

Sure. It's Dacy Gillespie and they are she her.

Maureen

Okay. Thanks so much. So you are an absolute pioneer in the intuitive style space and you've been leveraging principles of intuitive eating1 and Health-At-Every-Size2 in your work as a stylist, well before these were well known concepts. So would you just briefly define these terms and share how you incorporate them into your work?

Dacy

Intuitive eating is a I guess you would call it a kind of a method or a way of of eating that was, you know, written about in a book by Evelyn Triboli. And in the book, there are some principles that are outlined. And, you know, the basic gist of it is that our bodies are, you know, diets restrict what we can eat, and then our bodies don't get necessarily what they need. And when we're not listening to our bodies, we're not allowing it sometimes everything that it needs. And then we also have kind of a rebound. Like if we're restricting, then often our bodies will try and make up for that, like as you know, as they, you know, should naturally. So the concept of intuitive eating is a is about it's about a lot of things, but it's about kind of trying to learn your body's cues, listening to your body, trying to determine what it needs at different points, and not demonizing that and just allowing that.

And generally, when you begin to practice intuitive eating, there's a long period of time. It could be years where your body is recovering from that restriction and it may feel like it's kneading too much, but it's really recovering. And, you know, ultimately the I guess the outcome, the goal would be to really be in tune with your body's signals and feed it accordingly. There's a lot more, of course, that goes into that.

Health and every size is a concept that just simply means that you do not have to be thin to be healthy that people at any size can be healthy, and that we cannot look at someone and judge their health by their size. And again, lots more to unpack there. But, you know, that's the basic gist of it. how do these concepts fit in with your approach to styling? If you are trying to change your body or if you are not happy with where your body is, it's going to be very hard to get dressed. It's going to be very hard to figure out your style. It's going to be very hard to detach from kind of societal pressures and external messages about what you should wear, because we get the same kind of messaging from diets, right? This is what you should be eating. Listen to this expert. Ignore your own cues.

When I first started working with women to help them with their closets over and over and over, I saw that we couldn't make a lot of progress because everyone was trying to change their body or to revert back to a previous body that they had had. And so, you know, we couldn't we could. But what was keeping women holding on to clothes was the idea that they should be another size. And then if they held onto those clothes, maybe that would motivate them or with shopping or, you know, with shopping, it was like, well, I'm you know, I'm going to deprive myself of clothes that fit until my body fits a smaller size.

And in terms of developing their style, they couldn't look at an image of an outfit or any particular style without relating it to whether it would look good on their body. You know, everything just kind of came back to that. And so it started to be clear to me that. We needed to talk about those concepts. We needed to give permission and talk about the fact that, like, your body can be okay where it is. You can work on accepting your body. It's a very long journey. I don't think anybody in this day and age is ever going to get there. But, you know, we need to be open to these concepts if we're going to be able to work on our style.

Maureen

I mean, already it just so aligned with what I have experienced personally and then I've been in the observing of style online space for a while and I just completely agree that it's it's so difficult to really understand or define your personal style when you can't accept your body the way it is. And it's just. such a blocker. You have a notable style column on Substack called Unflattering Just one last definition. What does Unflattering mean to you?

Dacy

Well, I think we have to start first with what flattering means generally to most people and to most people. It's really something that they strive for. Again, in my experience working with women. For many of them, that was the top priority in their clothing. Whether it was flattering or not was more important than whether they even liked it. Certainly more important than whether they were comfortable. And and yet the real if we kind of like, you know, are honestly looking at the meaning of the word, what it really means in our common usage is to use clothing to look as small as possible. And so I just want to reject that concept entirely. And so to me, I wanted to kind of reclaim this idea of something being unflattering. You know, like the idea that you would never wear you would never choose to wear something that was unflattering. I just wanted to push back against that. And I guess, give everyone permission to not have to aim for that as the goal.

Maureen
Would you share a little bit more about that idea of giving permission? one thing that I consider sometimes, as I enter the space of sharing what I wear online. And, you know, there are aspects to being flattering that I still resonate with around color or even just sometimes a garment that is flattering is also comfortable because it respects the shape of my body. For example, you know, I have curves. And if I wore something that was boxy and didn't really respect the shape of my body, that also might be uncomfortable because it doesn't fit. So would you maybe share a little bit of your perspective on, you know, the difference between perhaps rejecting unflattering as something that we live within versus accepting the aspects of flattering that also just make sense for us. Do you have a perspective on that?

Dacy

Absolutely. I mean, I think that there are certainly uses of the word that are not kind of aligned with diet culture or, you know, the beauty ideal. And you mentioned, you know, a couple of them. Perhaps you like certain colors on yourself. Sometimes you put on a garment and you just light up a little bit and, you know, and other people would say, that's flattering because you look happy in it or because you look comfortable. But not to put you on the spot. But even the example you gave is that is your personal preference. And so you're able to say, well, I prefer clothes that align to the curves of my body a little bit more, but someone else with the exact same size and shape could if they wanted to reject the idea that that the clothes had to fit the curves of their body. And they could say, I actually really prefer this androgynous, boxy look where no one can see the shape of my body. I prefer to, you know, not be perceived in that way. And so, again, it's really about making that choice of like, do you want you know, if you break down the components of it, do you choose to do the pieces of it, you know, that are typically aligned with that word? And if so, that's great. That's your choice. I think it's more just like when it's a cultural pressure to conform to that is when it becomes a problem.

Maureen

Totally following you. Yeah. And I think that's I mean, the whole point of this podcast and, you know, the work that I do on Clear Day, which is is basically how do we do the work to to listen to that inner voice so that when we get dressed, we are we're choosing things that feel authentic and, you know, maybe, maybe quiet the external gaze that we push on ourselves because we've seen it from other people. So, yeah, I mean, absolutely. Do you have any kind of key practices or things that you do with clients or even just for yourself to to listen to that inner voice and that inner knowing?

Dacy

One of the first things that I do with clients is that I give them really specific instructions for creating a Pinterest board. And so what I want them to do, and it's a very hard thing to do and you can only attempt it. We can never completely, you know, achieve this. But what I want people to do is to be able to look at an image of an outfit and be able to try to separate whether they like the image esthetically or whether the negative thoughts pile in on top of their esthetic preference, saying, well, you could never wear that or that wouldn't look good on you or that wouldn't fit your body correctly. And so what I really want to establish before we talk about fit or, you know, finding the clothes that fit your body, I really want to establish what you like esthetically aside from those things. And it is, like I said, it's extremely hard to do.

Maureen

And in every aspect of your work, you acknowledge that. Leaving space for imperfection, right? I don't think that we're striving for perfection. And as a recovering perfectionist myself, I think it's so important to always caveat, like, these are things that we're trying. These are things that we're working towards. And I mean, I don't think that from anything I've heard from you, and certainly I don't think that there that there is a version of being able to completely strip what we visually like from, you know, the things that we have in our head. And, you know, if we want to talk about meditation, it's not about trying to quiet those thoughts necessarily. That could happen over time. But to me, it's more about acknowledging when those voices are there and hearing them and trying to decide for yourself if that inner dialog, whether it's supporting your needs or not. I'm just curious if you have any perspective on on any of that or if meditation is even part of your process.

Dacy

Yeah, I have tried to meditate many, many, many times over the last 30 years, and sometimes I will pick it up and stick with that. And then and then I had kids and it's funny because but I really, really love what you said about that, about just the noticing. And I think I'm going to start using that as well, because you're absolutely right that, you know, that would be really helpful, I think, for people to hear, to say, listen, we know those thoughts are going to come up.

Maureen

The other thing, too, that I've learned through a mindfulness practice is those thoughts that we might have, that we notice they don't necessarily require any action whatsoever. Yeah, just knowing that we are not our thoughts and they're just kind of things that like clouds float through the sky, you know, we're going to have these thoughts and we, especially if we associate our intellect with our thoughts, which I think a lot of Western culture we do that, you know, we are inclined to to take action because I had this thought, oh, that means I need to do something about it. And I think, you know, part of my mindfulness practice is like hearing those thoughts and deciding which ones to act on, if at all.

Dacy

And I just to interject. Yeah, I mean, my business, you know, my substack is called. I'm flattering. My name is Dacy Gillespie, but my business, the name that my business is under is mindful closet. And that is because that mindfulness and that noticing and that what I really think of and and name as a pause is a huge piece, I think, of how we work on all of this. Right? Because if you think about the noticing and then not taking action, as you were just saying, that really can come in handy when people are making impulse purchases or when they are tempted to, you know, buy a lot of extra stuff. And so that was definitely a part of the impetus for that name.

Maureen

Well, that so just talking about your personal style a little bit. So I'm generally more interested in the why behind how folks dress rather than the what, because, you know, getting dresses is so personal as we've been talking about in broad strokes, how do you decide what you want to buy or wear?

Dacy

Yeah, I mean, that's such an interesting question. I, I not, you know, overuse the phrase. But I do think it's very intuitive for me. I mean, I really it was something that I started paying attention to probably 15 years ago, maybe a little bit more. And what I started paying attention to was just the amount of ease I felt in certain clothes versus others. I really have always loved fashion, and for a long time I worked very hard to try and be the most fashionable person in the room or to be the most well-dressed, or to show that like I knew what was happening on like Fashion Week, you know, runways. And I finally kind of and I will say also that led to me buying a lot of stuff. A lot of it was secondhand and and it wasn't necessarily an issue financially, but there was still a lot of stuff. I mean, a few years before I started my business, I had two extra clothing racks full of clothes in my basement.

And so that process really was what I started personally to kind of that noticing, to figuring out. And at that time, you know, I was in my mid thirties, early to mid thirties, life was pretty chaotic and I just needed I have a lot of anxiety, you know, I have potentially undiagnosed ADHD and what I needed at that time was the most simple and the most comfortable yet also somewhat unique pieces. And so that that was that style evolution. I know. You know, and in the list of questions you sent over, you asked about different phases of my style, of which I've had many. Yeah, and most and most people have. But that phase was really very minimalist and it felt really good over time.

I am someone who is aware of trends and aware of just kind of how the fashion landscape is evolving. And it's something that I like to keep up on and I like to kind of be able to visually represent that. I keep up on that, you know? And so. Part of the choices I make are little updates here and there, you know. And it again, it is just fun for me.

And I really, again, want to give permission and to tell everyone else that you can opt out of that if if that's not something you want to spend time and energy on. But for me, again, it's something I enjoy. And so, yeah, it's a combination. And then it's, you know, pieces of my personal style come from the fact that I work from home, that I have two young kids, that I live in the Midwest. I think my style would be very different if I lived in, you know, as I did many years ago in Manhattan. You know, there was a lot more internal pressure and external pressure to make more of an effort to dress up more. And that sometimes resulted in me being less comfortable. And right now, comfort is is a big priority.

Maureen

I love that you're having fun with getting dressed right now. I know. You know, I've gone through different phases where getting dressed is so fun and shopping is so fun. And then I've gone through phases where shopping is anything but fun. It is difficult, it's expensive. It's you know, you have all these inner voices. I'm assuming that comes up with your clients. Have you had any kind of stories where you worked with someone that was not able to have fun with clothing? And maybe through working together, you were able to see that fun aspects come back if they'd ever had it before.

Dacy

Yeah, I mean, honestly, that happens a lot and it's super fun for me too. I mean, I just got off of a try on session with the client a couple of days ago who and many people say this, they they always say, oh, that wasn't as bad as I thought. That was actually kind of fun. Yeah. And I think it all goes back to that original concept of these need to be things that you like.

And I think that sometimes and I don't know if this has been the case for you personally, but a lot of times what makes getting dress not fun is that you feel so much pressure to please other people. And then also you feel that if you're not doing it in exactly the right way to please, you know, others or to, you know, be trendy, or then there's a lot of feeling bad about yourself.

And so I think another thing that probably makes it a little more fun for my clients is that that they have help, honestly. And, and when I just said that, a lot of people feel bad that they're not what they feel, they're they feel that they're not doing it it meaning, you know, getting dressed. Well, it's because we've kind of, I think, been conditioned as women, as females to think that this is something we should know innately. And I think it's really, really important to acknowledge that developing your style, ease with getting dressed. All of those things are skills. Just like accounting is a skill, you know, just like playing an instrument is a skill.

I just had someone I talked to the other day and we were just getting started and we kind of reviewed like her past relationship to clothes. And in every phase there was someone dictating what she had to wear. You know, at first it was her mother, then it was maybe, you know, trying to keep up with her friends. And then in when she began working, it was a very clear dress code and, you know, on and on. And so basically, you know, she's in her forties and I said to her, I just want you to be aware that you are in your infancy of developing your style. You have never been able to ask yourself what you want to wear because you've always been told what you had to.

Maureen

That's so powerful. So many people when you think about the skill of getting dressed, aside from the fact that probably people don't even think it is a skill, if they do think it's a skill, it's probably associated with, you know, this person that I see online has that skill and it looks like this and I can't do that. So I don't have the skill of style. And I think, you know, in my journey of of dressing authentically and intuitively is was so much of rejecting my attempts to force other people's dressing on myself. And, you know, I'm also having fun getting dressed again because I stopped assuming that to have style meant that I had to mimic someone else and that, you know, every person has style and every person who gets dressed in the morning or even those who don't get dressed in the morning. That is style. And I think to me, it's about accepting whatever your style is, you know, and that is almost the skill is accepting your personal preferences. It's really that skill of listening and and taking that on. I love to see that, that's something that you, experience frequently with your with your clients.

Going back to the idea of style revolution and you talked about, you know, that minimalist phase. Any other kind of memorable phases? Or if not, what? Where are you today?

Dacy

As I said, I loved I've always loved clothes since, you know, as long as I can remember as a child. And so I'll run through my phases real quickly, because one thing that I do with my clients and it's even a column on my substack is we talk about style stories and and then every time I run one of my group programs, we talk about style stories. And so my own style story is very fresh in my head. And what that means to me is just thinking back through what were those phases? What did you feel good and what were the messages you got? And then that to me is all valuable information in knowing maybe why you've made the choices that you have. And then once you can acknowledge those things, you can decide whether you do want to hold on to that thing you were taught or not. So for me, I grew up in a family where my parents were I guess you take, what, countercultural? And they did not care about clothes or decorating our home or would not allow me or my sisters to wear makeup or get our ears pierced. We were like a brown rice household, you know? And so they did not encourage my interest in clothes at all. And I never had. And we also didn't have much money. And so I never had kind of like the things that the cool kids had. So for me that really, you know, has been a lifelong thing of trying to notice, like, do I want this thing because it's like the end thing to have or do I want it because I like it? Then in high school I really am going to date myself here, but I was in high school in the nineties and I really got super into the grunge thing. So like my favorite outfit I remember was like the black and white striped tights under like a pair of cutoff jean shorts in college I, I dressed pretty traditionally and I was a little bit more dressed up than everyone else. And then I would say my twenties were really that phase that I mentioned earlier of, you know, buying and trying a lot of stuff and trying to, you know, just really kind of be a little bit out there, honestly with my clothes. Then then came the minimalist phase and, and I'm still in that. I still don't like to have a lot of clothes, but lately I've been introducing more color and a little more. Well, I've always ever since that I would say one thing, you know, that that is interesting that I think a lot of people will relate to is that for a long time, part of my style goal was to look hot. And so, you know, when I started wearing clothes that were unflattering, there was a whole different level of freedom. I didn't have to hold my stomach and I didn't have to worry about how guys would look at me and, you know and that I've never gone back because that's it feels so much better. But yeah. And so since I kind of gave myself that permission, I've always loved kind of oversize clothes and and things with a little bit more volume in them. And so, yeah, I'd say right now I'm, I'm still minimalist, I'm still pretty classic, but lots of volume. Some blocks of bright colors, but not a lot.

Maureen

Do you have any style or personal goals that you're excited to work towards this year?

Dacy

You know, we're recording this, I think, on January 16th. And to be perfectly honest, I don't think I've really processed 2024 yet. Yeah, you have something that I know about myself that I didn't know for a long time is that I do processing slower than maybe other people. I often need a longer period of time to make a decision. That goes for trying on clothes and and shopping as well. And so, no, actually, at the moment, I don't really I don't really have anything intentionally planned for this year.

Maureen

I think that's super valid, too. You know, so selfishly, I'd love to get your perspective on something that I've been struggling with a little bit, which is wanting to dress authentically for me, which in large swaths of my life I do, but also recognizing that sometimes life is easier or safer when we dress to conform. So, for example, I'd love to stop removing body hair that folks have determined is gross on women. But, you know, also being in a bigger body now, you know, I'm not necessarily in like a state where I'd like to draw more attention to myself in that way. Do you have any recommendations on how to balance that perception of safety with also living authentically? I mean, I'm sure so many people can relate and in different ways.

Dacy

Yes. Gosh, I have so many thoughts and I hope I can remember them all to get them. I mean, the first thing is this is the perfect opportunity for me just to acknowledge and for us to acknowledge that as much as we want to wear just what we like, it's not possible for everyone. It really isn't. And the more marginalized your identity, the harder it is for that to happen because you literally might be punished for it.

You know, if you're a black woman and you don't straighten your hair and that may prevent you from moving up in a corporate environment or, you know, if you're trans and you could literally be susceptible to violence. And so this is that, you know, you bring up just such a good point that sometimes we can't do that.

And in a way, I think this relates back to intuitive eating because one thing I think that people misunderstand about intuitive eating is that you always eat whatever you want, whenever you want. And one thing that they do make a point of intuitive eating is that you still have to plan around your life. You still have to be realistic, right? And maybe financially you can't eat everything you want to eat whenever you want to eat it. Or maybe you're going to be in a meeting over lunch and you need to bring a granola bar, you know, even though that's not what you above all want to be eating then. And so I think that that's what we have to bring in to the idea of intuitive dressing as well as like in an ideal world maybe these are the things I would do, but for me to feel safe right now, it is important for me to do these things.

And again, I to me it comes down to a conscious decision. You're not conforming just because you've been taught that what to do and you've never questioned it. You have questioned it, and you've made a conscious decision to say, I wish I could not do that right now, but again, I don't feel safe enough. And so I'm going to continue doing this.

Another big thought that I have is that sometimes it just takes time. And so I know when my body has changed. There have been years where I didn't feel like I could show my midsection at all because I just didn't feel comfortable. And then after I truly had a couple of years to get used to that body and that belly, it wasn't quite as scary anymore. And then I could, you know, maybe tuck things and have more high waisted stuff showing.

So I think you really have to give yourself grace in that area. And a lot of people will go. So far to the other side that they'll beat themselves up for saying like, Oh, I'm a bad feminist if I don't, you know show my belly or if I don't stop shaving or whatever. And to that, we just have to remember that this is the world we're living in. Of course, we wish it was different, but it's not.

Maureen

I mean, super powerful. I mean, and I totally love the connection back to intuitive eating. I personally, you know, I think a big part of my style authenticity journey that I've been on over the last year really started with working with a dietitian ostensibly for IBS, irritable bowel syndrome, realizing that I could benefit from intuitive eating and home in every size practice through working with that dietitian and, you know, really taking that lens to my closet and saying. Am I putting these clothes on my body because they're serving me? Or am I putting on these clothes because I think I'm supposed to wear them? And so much of that was I'm supposed to wear them because they make me look this certain way that you would be thinner or taller or whatever. And, you know, there are certain aspects to to your point that I still prefer because they are. And the overlap between my personal preference for fit and comfort, but also do serve in some ways the perception that I still, you know, exists within as a female in this country. I think it's just also related and just that ability to to discern. You know, again, going back to meditation and mindfulness, there's a concept of discernment which is, you know, being able to. To know what is and isn't worth your effort and your energy. I mean, I'm sure you could define discernment in a much better way, but just being able to know for yourself what is authentic and what where it's stemming from. And I personally think that comes through a practice of learning to listen and and going back to learning style as a skill, you know, that comes at a time just like accepting your body for what it is right now as it changes. Is is also a skill that takes time.

So just one last question before we wrap up. So understanding that you are a very experienced stylist, as we've talked about. What advice would you give to someone that's trying to build a wardrobe that feels intuitive and authentic to them other than following you on or. Sorry, unflattering?

Dacy

Oh, did you say Unfancy?

Maureen

Yeah, sorry.

Dacy

No, that's pretty much just a callback. Well, that is so cool. Yeah, but Caroline, whatever her name was with the capsule wardrobe. Yeah, that's so funny. Don't worry about it at all.

Well, I think one thing I just want to, like, free for you personally. I just want to make sure in what I just said that I gave you permission and that you give yourself permission to wear the safe clothes when you need to feel safe. You know, I just want to make sure.

So I think the best thing that people can do is listen to this conversation again. Really everything we've been talking about to mean the first step in any of this and in learning to dress authentically, eat intuitively, you know, make career choices authentically, is that awareness and that noticing And so, you know, take three weeks and just notice when you get dressed, how many things do you reject because you don't like them or how many things do you put back in the closet or throw on the floor because they don't fit? Right. Just starting to notice your preferences. I mean, really, that's where everything starts.

And once you have a little bit of a semblance of that in place, I think the next step is, you know, going on Pinterest, getting some visual inspiration, and it just goes on from there. But again, I really think the most important thing you can do is start to pay attention to what you like, why you like it, what you don't like, why you don't like it. Maybe if you have something you don't like, why on earth did you buy it? You know, I mean, almost maybe journaling a little bit about it every day, like what you notice. Truly, I think that's the the best, most impactful thing you could do.

Maureen

And if I could say one step further, is also just taking the moment to say my preferences as they are are valid. Yes. You know, when you take those pants off because they don't fit. Right. You know, someone else could say those pants fit you just fine. But if you put them on and they're not comfortable and they don't fit according to your standards, that is 100% okay. And that's the end of the story. That's enough. I think that's how that acceptance comes generally, is just listening to those preferences and letting that be valid.

Dacy

Yeah, I completely agree. And and, you know, I really think of the way that I work with clients is not I always tell them I'm not you're not a paper doll. You're not a Barbie. I'm not going to dress you. My job is to kind of be your guide to help you figure out what it is that you like. Because ultimately, that's the bottom line. If I tell you, you should buy something, but you'll never wear it. That's just a waste.

Maureen

Yeah, yeah, yeah. That's de-influencing right there. Yeah, that's that's the core of ‘under-consumption core’.

Dacy

Oh, yeah. The salespeople at Nordstrom used to hate to see me coming. I was. I was always picking everything apart and saying, you know, need that. Yeah.

Maureen

Oh, gosh, I love that so much. Well, I mean, this has just been so much fun. Some of the most fun I've had in a while, actually. So thank you so much for your time. And. Where can listeners find you?

Dacy

Sure. Well, you know, my substack is where I'm spending a lot of time. It's dacygillespie.substack.com. Or you can just look for Unflattering on Substack. And then I'm also I have my business website at Mindful Closet Dot Dotcom and I'm on Instagram at my info closet also TikTok but who knows where that's going?

Maureen

So again, this was recorded early in 2025. Okay. So I'll also make sure to include all your links along with this episode. And yeah, thank you so much.

Dacy

It was super fun for me, too, Maureen. Thanks for having me.


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1

https://www.intuitiveeating.org/about-us/10-principles-of-intuitive-eating/

2

https://asdah.org/haes/

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