Modern Arizona

How To Dress Like a Boss (after divorce!)

December 22, 2022 Attorney Billie Tarascio Season 6 Episode 2
How To Dress Like a Boss (after divorce!)
Modern Arizona
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Modern Arizona
How To Dress Like a Boss (after divorce!)
Dec 22, 2022 Season 6 Episode 2
Attorney Billie Tarascio

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What do you want your first impression to be? What is your brand? If you're a newly divorced man or woman, you know that it's time to throw away the trappings of the old you because they're just not working any more. That's what The Fabulous Deanna Dupree is going to help you with right now.

In this episode of the Modern Divorce Podcast host Billie Tarascio talks with Deanna about how she became the personal coach to so many women and men who are looking to rebrand themselves in a new and more positive fashion - even if they know nothing about fashion. It's the kind of makeover that can life spirits, bring success, and help you grow as a person.

To find Deanna online, stop by her Facebook group or her website at

Show Notes Transcript

Send us a Text Message.

What do you want your first impression to be? What is your brand? If you're a newly divorced man or woman, you know that it's time to throw away the trappings of the old you because they're just not working any more. That's what The Fabulous Deanna Dupree is going to help you with right now.

In this episode of the Modern Divorce Podcast host Billie Tarascio talks with Deanna about how she became the personal coach to so many women and men who are looking to rebrand themselves in a new and more positive fashion - even if they know nothing about fashion. It's the kind of makeover that can life spirits, bring success, and help you grow as a person.

To find Deanna online, stop by her Facebook group or her website at

Dress Like A Boss After Divorce

[00:00:00] Billie Tarascio: Hello, this is Billie Tarascio with another episode of the Modern Divorce podcast. Welcome back. Today is gonna be a super fun episode. We are talking with a local stylist. Now, when I first heard stylist, I thought hair stylist, but no, we're not talking about hair stylists. We're talking about personal fashion and accessory stylist, which is so, so fun.

So the fabulous Deanna Dupree, welcome to the show. 

[00:00:31] Deanna Dupree: Thank you so much. Thank you 

Miss Billie. I'm so happy to be here. 

[00:00:35] Billie Tarascio: Absolutely. I'm so happy to have you here. I love that your name on on the video is the fabulous Deanna Dupree. 

[00:00:42] Deanna Dupree: It's so crazy. My ex-husband gave me that name. 

[00:00:44] Billie Tarascio: He did? 

No. You and I met at a local event for women, which was super cool.

It was so great to meet you there. And you're a recent transplant to Arizona, right? 

[00:00:57] Deanna Dupree: Yes. I just, um, moved to, [00:01:00] uh, Arizona from California, actually, um, from a beach city and ooh, it's so different to leave the beach and go to the desert. Yeah. Um, but my soul needed this desert energy, so it's, it's exciting to, to be in this new, yummy place.

I love it. Desert 

[00:01:15] Billie Tarascio: energy. Tell me, what's that? What is desert energy? 

[00:01:19] Deanna Dupree: Desert energy feels like grounding solid foundation and just having that nomadic personality, you know, just, you know, kind of here and there. It just feels good to be planted. Yeah. And the desert, the mountains make me feel so secure, so protected.

Um, safe to just be still, which is something I've, never done . 

[00:01:48] Billie Tarascio: Illness is hard. It's So how did you become a stylist? 

[00:01:53] Deanna Dupree: Uh, again, ex-husband . It's so crazy. 

[00:01:56] Billie Tarascio: For real?

[00:01:58] Deanna Dupree: For real. We would, um, we would [00:02:00] go to dinner, go places, and people would just go crazy over my clothes and one lady. Literally bought the shoes off my feet at a restaurant in Orange County, bought my shoes and that night we sit down, uh, she gave me all this cash.

It was crazy, Billie. And she took my shoes and he said, do you, at one point, are you gonna see your effect on people? And like you have something, you know? And I was like, what am I supposed to do? Like what There is no, you know. And I told my mom that night and she said, you think Oprah shops for herself?

And I was like, oh. It had never crossed my mind that that was like a real career. I thought it was very, um, Uh, shallow to wanna shop for a living. And, um, I started looking into it and there was a real school I heard about fit. I would just totally close off to all possibilities. And at the moment I started to, at the time I was doing social media management for all these like, you know, corporate com.

I told them, they were all like, [00:03:00] that's you. 

[00:03:01] Billie Tarascio: Wow. 

[00:03:02] Deanna Dupree: And I was like, hi, does everybody see that from me? 

[00:03:05] Billie Tarascio: Wow. So you shop for people for a living? 

[00:03:08] Deanna Dupree: Yeah, that is my job. Okay. 

[00:03:10] Billie Tarascio: Okay. So I wasn't, I wasn't sure if you were just helping people, like if you were just consulting with them, but you are, you are a, a full-time 


[00:03:18] Deanna Dupree: Yes. I'm in. 

I literally, day to night I'm shopping. 

[00:03:23] Billie Tarascio: Wow. 

[00:03:24] Deanna Dupree: Feeds my soul. It's the, it's the, it's the best job in, in the world. 

[00:03:30] Billie Tarascio: Wow. Wow. 

[00:03:31] Deanna Dupree: Yeah. Okay. Okay. 

[00:03:33] Billie Tarascio: So are all of your clients like Uber Rich or who works with you? 

[00:03:37] Deanna Dupree: No, my clients. Our clients, they're Divorcee's , they are empty nesters. They are entrepreneurs.

They're just launching a company. They've lost weight. They've gained weight. You know, they. They want something new, Billie, you know, and they, they, they feel like everything that, that they're looking at dressing in is just not who they [00:04:00] are. They don't feel yummy anymore, you know? And so their budgets aren't humongous, you know, but I make it work.

I'm a wonderful shopper, you know, I'm that girl. Well, I'll go to like, girl, I found a Gucci bag, you know, and I'm her, you know? And so, um, You know, I make you work. I, I just want women to feel alive, you know, and to know that there's possibility, you know, and that came, you know, I was married and then, you know, our Divorce it, it, it, it, it murdered me, you know?

And so I was down for be five months just in the dark, you know, literally like in the dark. And when I finally. Came to light. I, it was a phone call. Mm-hmm. from someone that heard of me and asked if I would take cash if I would shop for her. And that was, it changed my life because I was literally, I had seven bucks.

Yeah. Literally, you know, and it was just like, it was a call from God, you know?

[00:04:52] Billie Tarascio: Yeah. 

[00:04:53] Deanna Dupree: And, um, noticing that that was my, that was my girl, you know, the woman that was just like me, you know, just [00:05:00] coming out of a bad situation, needing to find herself again, starting with outside and then in, so. 

[00:05:06] Billie Tarascio: Wow. Yeah. It's a, it's a, I got chills. I did. Yes, I did. 

[00:05:13] Deanna Dupree: It's deep, you know, and it led into becoming a life coach because I, you know, I'm in their closet with all this trauma and she's on the floor, I didn't know how to support that, you know? I'm like, oh my God. Like I just, Hit a nerve or I found something and I wanted to support that, you know, that revelation. Why are, why can't we let go of this outfit, of this dress, of this scarf?

Who was it attached to? You know, more chills and, um, . 

[00:05:42] Billie Tarascio: Wow. 

[00:05:42] Deanna Dupree: I, I told my then mentor, I was like, you know, I, I'm not helping my ladies. It, it's more than shopping, it seems like. And she's like, you need to really go get. The tools that you need, you know, and get certified. And I, I did. And so now it's, it's a, it's more than shopping.

It's a full experience, you know, it's, it's an [00:06:00] awakening. 

[00:06:00] Billie Tarascio: It's so cool. 

[00:06:01] Deanna Dupree: Yeah, it's beautiful. It's, it's beautiful. I'm literally living my dream. 


let's say somebody comes to you and they, they, they don't like their style. They're like, listen, I. . 

I don't, I don't, I don't know what to buy. Right. , that's always them.

that's always, you know, and so, which is, which is where I want you to be. I don't want you to come to me. Oh, I know who I am. No, you don't. You know what I mean? If you did, you wouldn't be here. Um, or on my phone. But I love when they're lost. Cause we get to go through a series of, uh, it's a journey, you know, of questioning.

You know who you are. Tell me about your day, you know. Your lifestyle, you know? You know, who's your style icon? That always helps me when they answer who they saw icon is. Mm. Um, and some say, I don't know what a style icon, like who's that girl that you remember looking at as a kid, as a teenager, as a, you know, young woman?

Like, ugh, if I could just, you know, sometimes it's their moms, their grandma, you know, someone that had just grace and beauty and that's all she really [00:07:00] wants. Doesn't really have a look. She just wants to just feel like a woman, you know? And that, that's my girl. Wow. 

[00:07:07] Billie Tarascio: Yeah. Very, very, very cool. I think this is so fun.

So what, what are the different ways that clients can work with you? 

[00:07:16] Deanna Dupree: Um, Um, I have, I have a number of ways. So what I, what I created for the girl who just could not afford like a full service. I do style challenges every month. Just a week. Yeah. And just, you know, seven day style challenge. And we'll do it on Facebook, on virtual, and it's a way, it's affordable.

It's like $99, you know, and you get me for a whole week on the phone, in your closet, on Zoom, on FaceTime. I'm pushing the envelope, you know, how would you feel in stripes today? Wear red lipstick today. You know, wear lace panties and we're just doing things to kind see what works for you and just kind of, you know, open you up some more creative, fun looks that make you feel yummy when you go out into the world.

So that's one way. I love that. That's a super fun way to, [00:08:00] to work with me. They can actually, if they wanna do a full closet, you know, overhaul, go through it. It's strenuous, but it's so good to just purge and let go of Oh yeah. It's good. Who you're no longer, you know, it's just mm-hmm. . The closet feels so much lighter when we come back into it.

I'm just, I walk in like, oh my God, it feels so heavy. You can feel all these personalities. Yes. It's heavy, heavy after I leave . Oh, I'm sorry, what? Go ahead. Go, go ahead. 

[00:08:32] Billie Tarascio: No, I didn't hear you. 

[00:08:33] Deanna Dupree: No, I have to like stage myself when I like leave their, cause it's so much energy, right? 

[00:08:40] Billie Tarascio: And like literal dust and literal weight of, of things that you literally, you haven't touched or you won't wear, or.

You know, a color that looks terrible on you or whatever. Yeah. 

[00:08:53] Deanna Dupree: Yeah. But that's where a lot, a lot of the hoarding, you know, we're so afraid to let go. You [00:09:00] know, like, I may get back into this, you know, I'm, I'm getting on this weight loss, weight watchers thing and I'm gonna get back, you know? But my response to that is, doesn't the new woman deserve something more yummier than this? I appreciate you getting back to her, getting back to that weight. But give her something new. Totally. Don't hold on. You know, like, get rid of this. This whole has old energy. It has, has a story that you're not happy with, so let's give her something new. You know? And that they, when I say that, like, okay, you know, but it's, it's heavy.

It's heavy. So 

[00:09:36] Billie Tarascio: how do you approach fashion trends? 

[00:09:40] Deanna Dupree: I don't, you don't? 

[00:09:42] Billie Tarascio: No. I love that. . Tell me more. . 

[00:09:47] Deanna Dupree: Um, you know, when, when, when I have my clients send me, you know, pictures of, you know, they send me all these Instagram pictures and Pinterest and I'm like, okay, so we're not gonna do that. We're gonna do it with your [00:10:00] flare, with your funk, with your fashion, you know what I mean?

So I may, I just don't rock with it. Billie, I'm a very classic, timeless dresser and stylist. And what cause that is the. That is the era of the woman, you know what I mean? When we were really feminine and soft and soft power. I'm not getting you in some halter dress with holes on the side. I'm not doing that.

You know what I mean? Because that's not who you are. Um, it's only a trend now and then you're gonna hate this picture in 20 years. 

[00:10:28] Billie Tarascio: Oh, right, or in six months . 

[00:10:31] Deanna Dupree: Yeah. Look, I'm not a trend follower at all. You know, I could even tell you what today's trend is. I'm not into it, you know, when I watch even fashion week, I'm just look going for the glamor, the elegance, the gowns, you know?

But I'm not watching for who's putting a silver hook and blue pants with a, with a. That's not who we are. You know, especially as women in business, as mothers, they're, they're, they don't, they're not into trends. They just wanna look and [00:11:00] feel good. So I'm just looking for what makes you feel like a million bucks, you know?

And it's generally not a trend, it's a timeless blouse, a timeless high waist trouser pan with a simple shoe and you just feel and look darling, you know? And, um, I stay away from the trends. 

[00:11:17] Billie Tarascio: Where are your favorite places 

[00:11:18] Deanna Dupree: to shop? 

 I actually like to shop at boutiques. I like unique pieces. I like thrift stores.

I like mm-hmm. , um, to find emerging designers. Mm. Um, you know, people, something that no one has ever seen, you know, but it's something that, I feel close to, you know, it could be a timeless white Oxford, you know, but it's just the fabric or the maker has such a beautiful story where I really want you to have that.

You know? So I try to stay outta the malls. Um, cause I don't want you to ever see yourself coming down the street. Never. It's like the worst thing besides could do is replicate a look nine times in the same town. I'm like, they all look, look alike. Why would you you do that? You know? So [00:12:00] I try my best to.

Go to, you know, unique, um, designers, boutiques, and, um, venture stores if I can. Now I do have clients who literally, really, they want nothing but Fendi Dior, but just how I would dress it, you know, so I did have girls that way. I'm like, okay, well I'll buy it. We're gonna spend this 30 grand. On five pieces and , you know what I mean?

I'm like, you wanna do that? So I try to tell them, let's stretch that. You know, I can, I can do a whole wardrobe, I can do a cap. So I do shoes, bags, belts, everything for that, versus just getting this boot, a shoe and two dresses, like mm-hmm. 

[00:12:41] Billie Tarascio: Thirty thousand??? People do that? 

[00:12:43] Deanna Dupree: Uhhuh, 

[00:12:45] Billie Tarascio: wow. 

[00:12:46] Deanna Dupree: Mm-hmm. I had a lady, she, she had, she was like, okay, I have 11,000 to spend.

And I was like, cool. You know, we can go, no, no, no, no. I want you to go those Fendi boots for me. And I was like, are you kidding me? You just told me you wanted, [00:13:00] like, you're ready for change. You're, you know. But she wanted this new Fendi boot that had just come out and it was 7, 7, 9, 5. Mm-hmm. . 

[00:13:09] Billie Tarascio: Okay. So those are not where I shop.

I didn't even know that Boots cost that much. I really didn't. 

[00:13:15] Deanna Dupree: Oh. Oh yeah. For sure, for sure. 

[00:13:17] Billie Tarascio: So, okay. Alright. So I feel like fashion is so powerful because it gives you the opportunity to express your brand a hundred percent. And Modern, Law recently went through a kind of a rebrand and mm-hmm. , it's great photographer and everybody is kind of doing this thing in this, in this new brand and it's been so powerful and I've never done it before.

Hmm. How do people find their brand? 

[00:13:40] Deanna Dupree: Ask yourself, how do I wanna be remembered? How do I wanna show up in the world? Mm-hmm. , you know what I mean? Mm-hmm. , if you wanna be known as this, you know, woman about town, or you know, this guy who just, you know, is just so. Fun and approachable and powerful and graceful, then that tells me exactly where I'm [00:14:00] not gonna shop.

You know what I mean? But I think if people really think about who they want, how they wanna be remembered, and how they want to show up every day, what, how do you want your kids to see you? Mm-hmm. your clients, you know, does your brand, um, Is your brand employable, which means like, you know, if, if a company wants to buy you, buy your company.

You know what I mean? Does it really mesh with the look that you telling me, are you worth what you're charging? Mm-hmm. , you know what I mean? Things like that. So go through those questions to really kind of see. What's the right brand color? Your logo, your look. Should, should, should you have a t-shirt on for this picture?

Should we have a, you know, a, a blazer on, you know, it really helps me when they tell me how they wanna be remembered. You know, how they wanna be known. I don't want to be known as. Just a shopper or you know, just this girl that is gonna just, um, you know, get trends and charge you with arm and the leg and just be about my, I want, I wanna be a part of the family, you know, I want you to be like, I know who I'm [00:15:00] calling for that wedding, for this event, for my next podcast.

Or, you know, because they trust me. They trust that I am gonna hold their brand in the highest regard that I would do my own. 

[00:15:10] Billie Tarascio: Okay, so what I've heard so far is you, do you do a weekly 


[00:15:16] Deanna Dupree: Uhhuh? Uh uh. It's a monthly challenge for one week for seven days, and 

[00:15:20] Billie Tarascio: that is $99. 

[00:15:21] Deanna Dupree: Yep. 

[00:15:22] Billie Tarascio: You will do special events, you'll go find outfits for events, special occasion.

Mm-hmm. . And then so somebody would give you a budget and you would be like, this is how much my fee is. Yes. The rest is what we can go, okay. Yes. Somebody can give you $11,000 and tell you to buy boots or Yes. Or more than that. Sure. Okay. or you do closet overhauls 

[00:15:43] Deanna Dupree: Uh, and then I do styling parties where, 

[00:15:46] Billie Tarascio: oh, tell me about that!

[00:15:47] Deanna Dupree: So fun. So you would like host it, you have your girlfriends come over and I would, so I tell everybody to bring some of your pieces that you just have had a, a problem dressing. Stop. I have [00:16:00] this dress, I don't know what to do with it. I love it, but I just don't know. Something's not right with it. Right? I'm like, okay, bring that

And I bring over like all my favorite foundation pieces. I bring over my, you know, some close from my old boutique. I had a boutique at some point. So I, I have a lot of pieces that I, um, I, uh, I travel with. I bring my belts, accessories, handbag, shoes, I bring all that. And so I kinda show you how to style it.

You know, some people purchase, some, just wanna know how to dress their bodies. It's always, you know, a nice party. I bring the bubbly and um, it's an amazing time, you know, and the girls, they give me for like four hours. It's just play, play, dress up. 

[00:16:37] Billie Tarascio: Well that sounds so fun. That sounds like a great quarterly thing for my company cause I feel fun.

We would all love that so much. Yeah. I I just think that's wonderful. Okay. Have I missed anything? How else can people work with you and where can they find you? 

[00:16:51] Deanna Dupree: They can find me, of course, on my website, I'm sure you're gonna put it in links somewhere. Of course. I, I'm very active on [00:17:00] Instagram these days.

I have a lot of fun there. Um, but I have a lot of women that just send me questions, You know, I see you posted that, you know, I'm having a problem with this. So I do a lot of consulting via Instagram, so that's fun. And then I have a Facebook, um, group called, um, dress Like a Boss with Deanna, like the Boss . And that one has about 300 people in there.

We just talk, you know, people have events, they have meetings. We're changing seasons, you know, should I change my hair color? There's all kind of questions in there, so we just talk. I'll go live every, every day and give a, you know, a style tip and, um, it's fun so they can find me there too. 

[00:17:41] Billie Tarascio: I have really, really enjoyed this very, very much.

I, I love meeting you at the event and Yeah, and it's been great to get to know a little bit more about you. I will be signing up customer right here. Um, and I, I would encourage everyone, especially like if you're going through a Divorce or maybe [00:18:00] you're even thinking about going through a Divorce, but you're not quite sure, like getting in touch with ourselves as moms, as women in our new roles.

Especially like as you move through ages, like yes, what works for you in your twenties isn't gonna work in your thirties, isn't gonna work in your forties.

[00:18:17] Deanna Dupree: Exactly.

And women, I want people to remember, you know, it's, this is the thing. How you dress is an exact representation of how you feel about yourself in your life.

Okay? And if you're still, if you're forties and 50 still wearing your 30 to 20 year old clothing, people are like, oh, she's, it is so many judgemental statements that I hear, right? But you're not even honoring who you are today. When you do that. You're not honoring who you're becoming, you know? And if you are becoming a divorcee, you're becoming a c e o. You're becoming, you know, this powerful anything, woman, man. Then dress accordingly. You know, sometimes we do need a trained eye. You know, your girlfriends can't tell you, oh yeah, that's so cute. It's cute. However, they [00:19:00] don't see these little, you know, minor details that I would see.

And so I really want women, and well, I, I have men clients too, but I want you to be able to see yourself as this, um, as a billboard. 

[00:19:12] Billie Tarascio: Yeah. 

[00:19:13] Deanna Dupree: You are a walking, talking billboard of your brand, of your personality, of your business, of your life. You are that. So you're showing the world without saying a word exactly who you are and who you're not.

So it's important that we, have the wardrobe to, that speaks to that. You know, sometimes my clients, I'm like, we don't need a hundred pieces. I can do a 40 piece closet and. Kill it. You know, you know how to mix and match. You have the, you know, five pants, two shirts, nine belts through your shoes, and we, we can work it, you know, it's, it's all possible, but don't stay in the past.

That's where, you know, you continue to wear your trauma and it shows up in your energy, shows up in your language, but definitely shows up, you know, in your, in your image. So, um, I want people to get outta that mindset. 

[00:19:57] Billie Tarascio: I have one more question. Do you Yes. Because [00:20:00] it feels like this would be a great gift.

Like I've got a brother who's turning 40, Uhhuh . I feel like he's going to the business... 

[00:20:08] Deanna Dupree: Yes, I've been gifted about 20 times. 

[00:20:11] Billie Tarascio: Okay, and how does that work? 

[00:20:12] Deanna Dupree: So someone will say, Hey, I have a, you know, a friend or a wife or whatever. I wanna gift you, I wanna gift your service. You know, it's pretty much physically I have like an actual voucher, but, you know, in, in, in just the business of it, it's a matter of them either.

Um, , they're gonna actually pay for the service or just ask the person, what do you want from, you want a full wardrobe? Do you want a shopping day? I wanna gift this to you. And I just work it out with an actual, with the buyer. But it looks like it's typically I start off with like a $500 gift card or a gift voucher, which will get us at least on camera, in person, let me see your closet, what are you working with?

Right? And then we can at least start there. And I know. I can see it, I can always feel it. Oh, I see. This is why they called me. Right. You're still wearing your, like Miami Vice suit from , [00:21:00] you know, with like holes in it. Um, so typically it's, uh, I've been gifted a few times. It, it's a wonderful gift to give, to gift of style, but it's a gift of transformation.

You know, it's of, of love, of lights, of newness that people just. I don't think it's possible, you know? And so I appreciate being that, you know, that gift to people. But yeah, gift to me. I'm here. Mm-hmm. . 

[00:21:22] Billie Tarascio: Okay. Love it, love it, love it. Alright, if you all have enjoyed this episode and I know you have cuz I have, unless you don't like fashion.

But, um, if you enjoyed this episode, rate it, download it, send it to your friends, go back, rate the other ones. And if you'd like to be on the Modern Divorce Podcast, make sure to reach out and let me know. Deanna. Thank you so much for being such a wonderful guest today. Really appreciate it. 

[00:21:44] Deanna Dupree: Thank you, Miss Billie gratitude.

You're amazing. 

[00:21:46] Billie Tarascio: Have a good day. 

[00:21:47] Deanna Dupree: I love what you're doing. Bye y'all. [00:22:00]