TAC C6E3 Jessie Chiang Interview Podcast Graphic

Hello and welcome to Talking about Clothes, with me, Holly Chayes, where I talk about clothes with people who wear them. This is the transcript for Using style to feel more confident and powerful – a conversation with Jessie Chiang. 

In this episode, Jessie and I talk about personal style as a way to feel more confident and powerful in business. Jessie is a past coaching client and was looking for help getting out of a style rut. We discuss how she learned to stop allowing her clothes to hold her back, and how to redefine what successful shopping meant (which inspired this blog post!). Jessie and I also talk about style and clothing as a form of self-care and embracing a love of fashion. 

We originally recorded this conversation in 2021, and I’m so excited to share it with you. 

We do talk a lot about bodies and sizing in this episode. So if that’s something that is sensitive to you, please please listen with care or listen next time.

You’ll find the rest of this season’s conversations and links to everything we mention at WhoWearsWho.com/podcast6 (And if you want your own help using personal style to feel more confident and powerful find out how we can work together here.)

So let’s dive in.

Jump to a section of the conversation: 


Holly  (02:17): Can you start with your name and where you’re located?

Jessie  (02:21): My name is Jessie Chiang and I’m here in Orange County, California.

Holly  (02:25): Cool, what do you do?

Jessie  (02:27): I am a spiritual business coach. I help spiritual women entrepreneurs to reach their goals twice as fast and under 90 days. Without the fluff. Without wasting time and energy.

Using style to express yourself

Holly  (02:40): And kind of diving into talking about clothes and bodies and the relationship between the two. When you think of clothing your body what do you think of?

Jessie  (02:53): When I think of clothing my body I think of it as a way to express my creative self without having to say much. I want to be able to step into the room with my clothes feeling like… I like the phrasing. “What you see is what you get.” So what you’re seeing with me is what you get. There is nothing to hide. This is exactly me. And my clothes tells you that about me. So, it is an extension of myself.

Holly  (03:22): What do you want to say?

Jessie  (03:25): I want to say that I’m just really confident with who I am. I’m a woman of integrity. I’ve been through a lot in life. That, I’ve seen enough that nothing can shock me anymore. And that I’m really here to add value in your life.

Jessie  (03:45): I’m a person who is a… I have a can do attitude. I want to go help people raise the vibration in the collective. So I’m just, I’m not here to just play around. I’m really here to do the work. So if you’re going to be a friend with me, or do, have any work relationship with me, you know that things are gonna get done.

Wearing style that make you feel confident and powerful

Holly  (04:08): Yeah, that’s awesome. How does that translate to like what you put on in the morning?

Jessie  (04:14): I feel like whenever I wear something I want to feel powerful. That I want to feel powerful for the day, get things done. I’m, so I don’t know if you speak about the human design. You know, the human design, I’m a generator. So I want to and I love feeling satisfied. What I’ve done for the day. Even if it’s just like you know, referring a friend to this friend because I know that they have a common audience and common topic, and that makes me feel good. Just because I can connect people together.

Jessie  (04:49): So yeah, that translate in a way that you know in the clothes that I choose in such a way I want it to make me feel good. Like today I have this actually I have a very colorful necklace that I wore for nine seconds. I took it off because it was just too heavy. But it did make me feel good because I had a talk before this. It made me feel good to just wear this with this black top. Because it’s powerful. Because it actually activate all your chakras as well. So I love that idea, of again, the spiritual connection, not just with the fabrics of things, but just what it means as well to me.

Crystal jewelry & opening chakras

Holly  (05:30): Yeah. Do you have like other examples of that?

Jessie  (05:34): Let me think. Well, I have a lot jewellery that are definitely made of crystals. So I know. Like if I’m going to be talking I’ll wear Aquamarine to help me open my throat chakras. I also have some clothes that I got from Bali the last time I visited Bali. So it always reminds me of that spiritual connection with you know how they’re very spiritual with their environment, the trees, the ground, the water. And so when I looked into some of this design from this clothes, I just instantly felt that connection was like going back to your core self. Going back to your soul purpose. Where are you heading? What you’re doing in this lifetime? So it reminds me a lot about that.

Decluttering to feel more confident and powerful 

Holly  (06:20): Yeah. Does that translate to how things feel physically in any way?

Jessie  (06:25): Oh, yeah, I think definitely. Definitely. I think all your clothes carry some sort of vibrations. I feel I definitely feel like all the things that I’ve taught definitely has carried some trauma. Small T trauma. You know whether it might be a time when you bought it, you might have a different idea around life and what you were experiencing that time. And as you uplevel those are the things that you no longer connect with. And the clothes still hold on to that memory. Interestingly enough.

Jessie  (07:03): So as soon as I toss a lot of those old memories, I and I kept the ones that bring joy obviously. I definitely noticed how fast I have advanced since being able to let go some of those old memories. definitely like, lighten you up and so it speeds things up. So then the more you wear those clothes that makes you feel powerful I feel hold a higher vibration it definitely lift you up faster.

Holly  (07:35): Yeah, yeah. Have you done like a recent closet clean out?

Jessie  (07:40): I did. I did over the winter break.

Holly  (07:43): Yeah. It’s as good a time as any.

Jessie  (07:49): I also didn’t have enough winter clothes, because I’ve lived in Malaysia for the last… What is it from 2013 to 2018. Those five years there and so I don’t have enough of that collection. So now that I’m here again, I need to have some cute clothes and things have changed and a lot of trends have change. So I figured you know I’ll get rid of some stuff and bought some new clothes so.

Choosing yourself over bad fitting clothes 

Holly  (08:19): Nice! Yeah. You touched on this a little bit, but kind of the relationship between our clothes and our bodies and past selves and future selves. And who we were and who we want to be is a very fraught relationship and can get complex at times. Yeah. So when you think about the stuff that like air quotes, “stuff” that clothing brings up. What does it bring up for you?

Jessie  (08:52): You mean my old clothes?

Holly  (08:53): Yeah, yeah, old clothes or what you don’t want to bring into your new wardrobe. That kind of thing?

Jessie  (08:59): Oh, yeah. When I was buying clothes, I was more this time around. I was more cognizant of how I want to. I want it to be a good fit, I want it to be just perfect for me.

Jessie  (09:10): You know, in the past, I would have just buy whatever that fits. Like, “oh, it fits. I’ll get it.” Because I was just really I thought my body there’s something wrong with my body. The clothes are right. And I think we talk about that like how is not really so much about our body.

Jessie  (09:36): But now I realized that “hey, there is going to be clothes out there that’s going to fit me.” So it’s okay to try them on and say “Hey, didn’t work so we’ll return it.” So this time around definitely a more critical of the fit and the colors and the way it makes me feel.

Jessie  (09:57): And sometimes you know, the clothes looks great online on the website. You ordered it and you wear it and it looks like. It looks like you have on a piece of bag. I just ordered this nice denim shirt. It is supposed to have this big bell sleeves. Looks great on a six’ two” feet model right and I’m only five’ three”. It really looks like a balloon on me.

Jessie  (10:25): So yeah, it goes back to the fit. I feel like you’ve got to have a fit. And I think you know you only own those. And knowing what works for you is great. But also how it makes you feel.

Jessie  (10:35): So at the end of the day I go with like, what, does it make me feel good about myself? Does it represent me and my values? You know, do I come across as Jessie Chiang? And not Jennifer Lopez you know? So yeah, I stand by that right now with shopping.

Confidently shopping for new clothes

Holly  (10:59): Yeah, I remember back to when we were doing coaching together one of your big revelations was that you don’t have to walk out of a store with any piece of clothing. Do you were there any instances kind of in this shopping? Not spree but obtaining new clothes…

Jessie  (11:19): It kind of was a spree…

Holly  (11:22): Fair enough. …is like getting a new wardrobe that you were like “there’s nothing here for me. That’s fine.” Like what’s, how’s your thoughts on that change?

Jessie  (11:34): Oh, yeah, totally change. I don’t feel like I need to pressure myself to get something just because I visited the store. And, you know, even though, yeah, I have some spare money to buy and I was like so determined. Like I would want to get this pair of jeans and I want to get this top.

Jessie  (11:53): You know, sometimes I even saw it online. And I would be like going to the store just to realize that it’s not what I expected. The fabric is too rough on me or anything like that. So anything that I feel is not a good match.

Jessie  (12:08): I think it’s also safe to say with like friendship and relationship like if it’s not a good match, it’s okay. We can live our own lives. We don’t have to argue. You know we can live separate lives.

Jessie  (12:19): So it’s the same way now with what I see in clothes. Like if it does not match me. It’s okay. I can walk away empty handed. And I know there’s going to be something out there that is going to be a good fit for me.

Holly  (12:30): Yay. I love it. I’m so glad.

Being confident enough to choose clothes that work for you

Jessie  (12:37): It is so much more peaceful when you would think of that way. You’re living in that abundance mindset, isn’t it?

Holly  (12:44): Yeah, and I one of the things I see a lot is kind of the clothes that hold you back that don’t feel good, were often things that we buy, because we felt like we had to get something. Even if it wasn’t the right fit. And that settling for clothes has long term implications that we don’t always acknowledge when we’re just picking that piece up.

Jessie  (13:11): Exactly. Yeah, exactly. I think the pressure was for me is I used to not have enough time so I thought and then not thinking, thinking that I don’t, will not ever find that perfect fit. There was something wrong with my body was what pressured me to must have that. Must have it because just because it fit. You know, even though size 8 didn’t fit, I’ll get a size 10 “Oh, it’ll fit” and I walk away with that. So totally wrong mindset I feel. Right now, I feel much more at ease with buying.

Holly  (13:44): Yeah, I assume you feel like you make better purchases is that accurate?

Jessie  (13:48): Oh yeah, totally better purchases. Better choices. Better wardrobe.

Wearing what you most enjoy

Holly  (13:53): Yeah, what do you enjoy wearing the most? Like what’s your absolute favorite item?

Jessie  (14:04): Um, you know, recently I just got this two blouse from Madewell. Because they’re made really well, I feel. They are. I just realized that I just noticed the quality in it in the clothes. So it was just this blouse, sleeveless blouse. It is a top with vertical lines. Off-white with pink lines. And the front is just a regular sleeveless top. At the back. It has a nice criss cross designed to it. And it has small buttons that hold the criss cross. And I love it so much.

Jessie  (14:44): I love that little details, those kinds of things, and it’s very texture as well. So I love the feeling of having a texture. Sometimes you’d like things smooth. Sometimes you’d like things a little rougher. I like that contrast. You know if I put a cardigan on it.

Jessie  (15:02): But it makes me feel really nice like feminine and cute and fun. You know, heading to springtime.

Jessie  (15:10): And then the other one was like a nice long sleeve blouse. Has this again, the balloon sleeves and with a peplum detail on it. It has a brick, it’s a brick color and at the back it has four buttons. And again, I just feel wonderful in it. I feel like it’s the really nice work from home type of clothes. And because of the brick color is kind of a bright red, orangey red. So you can really just stand out. Like if you on a zoom call among 24 people you’re the one who is gonna stand.

Holly  (15:46): Yeah, absolutely. And that’s something we never had to really consider before this.

Jessie  (15:52): And I have to also mention that there was this jumpsuit I think we talked about that. This onesie I got from Singapore. And it was long pants, jumpsuit, as a full wrap in the front with a drop sleeves and it has kind of a flare sleeve there. And then you have a tie on belt. As a whole it’s a dark navy. Whole thing is dark navy is just really plain but I love what it love is this expose a little bit of your shoulder where it makes things a little fun and sexy. But then the rest of it is like I’m in business too. Right?

Holly  (16:33): Yeah. And that’s such a balance to achieve and finding what your individual balances is always the key to that.

Jessie  (16:42): Yeah. And that’s essentially my business too.

Holly  (16:45): Yeah.

Jessie  (16:45): It’s about marrying both the spiritual practice and ancient healing methods with the practical strategies of business and marketing, you know, lead generation. So it really actually, like you said it’s fun and business as well.

Using style to feel more confident and powerful 

Holly  (17:00): So yeah, yeah, absolutely. Is there anything finally that you want to say about clothes and your body and feeling good and all of that?

Jessie  (17:10): You know, I came from a very long journey of not being not confident with my body. And I always thought that dressing up nice is a curse because then I attract attention. You know, I had been violated for long when I was a kid. So I assumed that was the case if I do dress up.

Jessie  (17:34): So for anybody who feels like “oh, you can’t dress up because you’re going to gain unwanted attention.” Or “that’s going to make other people feel intimidated because you dress up so nicely and so professionally.” To know that that is not your problem. It is theirs.

Jessie  (17:56): You have the responsibility to bring the light into the world. You have the responsibility to share your light. And the more you do, the more you’re going to motivate and inspire the people around you.

Jessie  (18:10): I have to say that a lot of people who have seen me on Instagram and see how I’ve been dressing up they were inspired as well. I have people who just commented and or text me and messaged me and said “Jesse because of you I feel like self care so important. I want to look like you – I don’t want to look you know tired all the time.”

Clothing as self care 

Jessie  (18:31): And it does take that effort to go for it because you want to look a certain way. Can you say it’s vanity? Not really. But it’s really about self care. It’s how you feel how you feed yourself emotionally, how you fill your cup. So, at the end of the day: is how do you want to feel?

Holly  (18:53): Yeah, I’m so glad you said that and brought it up. I think that we often overlook our clothes as a way of living self care throughout our entire day. Because we can either dress so that we feel really good and we feel really good the entire day because of that. Or we can dress in something that’s slightly too small. It’s slightly cramped. It’s not feeling great and you carry that with you for the rest of the day. So it’s a really important part of self care that I think gets lost in like bubble baths and reading on the beach.

Jessie  (19:31): Yeah, very much. It’s all the subtleties that you gain from wearing something that fits you and makes you feel good. I have a client who told me that before she had coaching with me that she would try to fit herself in this really tight jeans. And even though it was tight, she would still want to wear it because apparently it holds everything up. Right. But after coaching she started dressing and buying jeans that fits her size. So that tells you when you feel good on the inside it shows on the outside as well.

Dressing up and using personal style to feel powerful and confident every day

Holly  (20:05): Yeah, and I remember early in our coaching, getting you to dress up every day was a new revelation.

Jessie  (20:16): It was, it definitely was.

Holly  (20:17): Yeah, and it blossomed and bloomed in amazing ways.

Jessie  (20:21): Yeah, yeah, I think it also helps me to take myself seriously in my job. Because it’s so easy to think that “oh when you work from home then you can be, you can dress whatever you want.” You know you can put your a pair of slippers and you might even wear pajamas to work. And I think it’s such a bad habit. I won’t do that. I didn’t think of it that way until you brought that up to light. It’s when I started seeing “I am my own business.” So are you. And so how you carry yourself even though other people may not see you. But it’s being heard in your voice in the things that you do and the things that you post. People feel your vibrations.

Holly  (21:02): Yeah, and it distinguishes work and non work time. In a really important way. It’s very important to do.

Jessie  (21:10): Oh, yes, thank you for saying that. Yeah, yeah.

Holly  (21:15): Yeah. Awesome. Well, thank you so much for chatting with me.

Jessie  (21:18): It was fun. Thanks.

Holly  (21:19): Excellent. Yay

Jessie  (21:20): Thank you so much for having me.

Holly  (21:26): And thank you for listening. I hope you enjoyed this conversation as much as I did. You’ll find the rest of the conversations and links to everything we mentioned at WhoWearsWho.com/podcast6

Holly  (21:42): I’ll talk to you soon.

And remember if you want your own help using personal style to feel more confident and powerful find out how we can work together here.

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