![269 | When to Get Rid of Something and When to Try Harder to Style It [LIVE Coaching!] — Her Style Podcast | Shopping, Color Palettes, Fashion, Wardrobe, Outfits, Clothing cover](https://static.libsyn.com/p/assets/e/6/2/9/e629fc13e77601f416c3140a3186d450/269-When_to_Get_Rid_of_Something_and_When_to_Try_Harder_to_Style_It.png)
I love hosting free events, like our upcoming Wardrobe Revamp Bootcamp, for so many reasons. It’s exciting to provide a focused training and such a joy to see your transformations in less than one week! It’s a joy to hang out with you inside our...
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I love hosting free events like our upcoming Wardrobe Revamp Bootcamp for so many reasons. It's exciting to provide a focus, training and such a joy to see your transformations in less than one week. It's a joy to hang out with you inside our free pop up group and get to know you better. And one of the biggest highlights is having the opportunity to answer your toughest style questions in real time and coach a few of you personally along the way. That's right. We are already giving away tons of awesome prizes including 15 minute power style coaching sessions with me. And today you get to listen in as I coach our most recent prize winner, Meg on some extremely relatable questions and conundrums like when should you get rid of something and when should you work harder to try and style it? Will transitioning to gray hair impact my best colors? How can I wear deeper, darker colors without overwhelming me and I can't figure out my style words help. Yes. We covered all of these questions in about 15 minutes. You'll be amazed at what we can accomplish with even a short amount of focused time on you and your wardrobe. If you like what you hear in this episode and you want the chance to win a free style coaching session with me, then grab your free seat for the Wardrobe Revamp Boot Camp, head into our Pop up community for the event and enter to win this week's store Prize by Friday, September 5th. Press pause right now and go sign up at herstylellc.com Bootcamp for now, listen.
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In on this advice packed live coaching.
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Session on cleaning out your closet, wearing color with confidence, and finally figuring out your unique signature style. Enjoy.
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Welcome to Her Style Podcast where we're all about empowering you to show up and get dressed every day with confidence. I'm your host, he Riggs, a 15 year and counting certified image consultant and color specialist, ready to build a wardrobe and a personal style you love.
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Let's get started. All right, Meg, so thank you so much first for joining us for the Wardrobe Revamp Boot Camp. And thank you for playing along with our first door prize which we gave away last week. And you're the big winner. We get to do some power coaching today and as I mentioned to you before we started doing the live stream, I love this question. We are going to talk about how to know when to get rid of something and when to try harder to style it. So tell us a little bit more about what stage you're at in your wardrobe revamp and a little more about how this is affecting you specifically. So I can be sure to cover it appropriately.
C
Okay, well, first of all, thank you so much. I was so excited. I didn't think I could win, but I was so excited when I did. So it's a very generous door price. So my style journey began about two years ago when I was gifted a online style session with a stylist, and that's when I turned 50. And I think that's also a shift in life where a lot of things start kind of shifting. And so I started to look at style more consciously because I am not at all a natural. And so in the last two years, I've got a lot of tips and tricks from you and from other people. And what I'm realizing now is that a lot of things I have in my wardrobe don't really like, you say, light me up, or they are from times where I didn't know my best colors, I didn't know my body shape. And so now it's kind of hard because I have a lot of stuff in my wardrobe, and it works most of it. But, yeah, with the knowledge I have now, it's not ideal.
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Okay. So it's just not lighting you up or is exciting you as much as you might hope in this stage of your journey. And I want to say first, that's completely normal, because your wardrobe is going to continue to evolve and to grow with you. And so there may be periods of time where you feel more of a disconnect with what's in there. And it's not necessarily a problem. It's just good to have awareness about it. So I think it might feel a little frustrating when you look at your clothing, and it's not completely matching up the way that you want it to, but it's good to recognize that, and now you can feel empowered to start making some shifts and getting it more aligned with what you really want for this new season of your life and your style evolution. So I know that you had also mentioned to us that you were wondering about when is good enough, what you need to free you from your perfectionism, and when are you just settling. So that's what I really want to help you pinpoint today. And I know you are also so insightful to mention that you do tend to overanalyze things, which a lot of us do. I feel like we can start like, Over Analyzers Anonymous here in this group, but it's because you're being so conscious of what you're wearing and making sure that you're bringing in the best possible choices for your collection. So. So all of this is good stuff, and it's really helpful to notice. And so I just want to recognize first that this shows tremendous growth for you, that you're seeing some little, you know, areas to work on in your wardrobe. So I don't want you to get frustrated, but I do want to talk through some tips to help you feel like you know how to navigate this and what to keep, what to replace, what to let go of, and how to make some of those tough decisions, especially if you don't have somebody working alongside you in your wardrobe. So the first thing I want to recommend to you, Meg, is just to be okay with starting slow. For most of us, we don't have the luxury to just throw everything away and buy a whole new wardrobe overnight. That may be the case, and if so, then I think that's amazing. And just make sure you're being really strategic about what you buy. But if you're like, no, I need some of these clothes. I have to get dressed today, and I can't go out and just buy all new things, then I want you to start with by being okay with starting slow and remembering that it's progress over perfection. So, unfortunately, like I said, for most of us with doing our wardrobe revamps, it's not an overnight thing. It is going to take a little time to really sort through everything, to be able to find all of the pieces that you want to replace some of those items. And so it's kind of giving yourself permission to fall in love with the process and to enjoy taking it one little baby step at a time. And instead of needing to look at the perfect closet, just start to see little bits of progress happening. And that, I hope, will encourage you along the way. Now being more tactical in making some of these tough decisions. If you haven't already, I highly recommend that you download my closet Audit flowchart. It sounds like you've been following me for a little while, so you might already have that resource. Is that something you've.
C
I haven't looked at it yet. No.
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Okay. You're definitely going to want to grab that resource. It's totally free. I think you can get it at herstyle llc.com closet-audit but we'll drop the link in this post in our for the bootcamp after our session so you can grab that. And what's really helpful about that is it's going to help to remove some of the emotional decision making and some of that perfectionism, because what you're going to do is you're Going to follow the flowchart question by question, and it's going to direct you towards your best decision. So, for example, you're going to start by analyzing, does this align with my style goals? And you seem really clear about what you want your style to be, and you've already said some of the things aren't matching up with that. But then there will be a series of questions to help you figure out if it's something that instead of removing from your wardrobe right now, maybe you want to put it in a separate pile to replace. And, yeah, the beauty in keeping more things the first go around with your audit. This is what I recommend for the collective members. Sometimes people are really eager to just go through and get rid of everything that we're not in love with anymore. But like I said, if you want to start slow, I think it's helpful to be a little bit more conservative in your first phase of closet auditing and keep more than you let go of, even if you know it's not completely perfect for you so that you can get dressed so you can kind of work with it over time and really make more empowered decisions instead of just quick decisions that you might regret later on. A lot of the things that you might be frustrated with right now, you don't need to remove from your wardrobe, but you might want to gradually replace over time. So that's going to be helpful to sort through. It's not like keep or let go. It's keep, replace, maybe repair or alter or remove. So there's lots of different possibilities for what to do with your pieces. And that closet audit flowchart is going to help you really work through what the best possible category is to put those things in. So I definitely recommend checking out that resource. And then as far as your question about how to know when to let go of it and when to just style it differently or try harder to make it work. I think it's smart to give yourself a limit it, and maybe you're going to say, okay, for this piece, I'm not really excited about it, but I want to challenge myself to see if I could wear it differently or make myself more excited about it. And I would say, give yourself a week, or maybe give yourself a month and say, let me think about all the ways I could style this piece and wear it this month. And if at the end of the month I'm still just not feeling it or I'm having to work too hard to make it work, then you can decide, okay, I gave it my best shot. I'm ready to let it go now, so remember that too. It's not like you're making one decision. You can make it as a series of decisions and again, do it a little bit more over time instead of overnight. So I think if you want to go back to the shop. Your closet challenge, I don't know if you were able to join us for that back in April. The replays are still up, and we're going to cover other tips in the boot camp of how to wear what you own in better ways.
C
I actually did go to that one. I really enjoyed it.
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Oh, good. Yay. Okay, so if you took some notes from that or if you want to go back and revisit the replays, the link is still up. So you could go back and maybe refresh on some ways that you could restyle some of what you have. Give it a. Give it a try and see. And I. My philosophy is like, you never want to work too hard to feel good in your clothing. So if you're trying to make something work and it's just not working, then I think you can feel okay about letting it go and moving on to better things. And to that point, to know it's always better to have less items that you really love than a lot of things that you're not excited to wear. So if you can afford to pare down a bit and maybe simplify, I'd rather you have, you know, four tops that you absolutely love that you can rotate more often than having 14 tops that you're like, I don't love the color on me. I don't feel good in this. I'm not confident wearing it out of the house. Again, I'd rather you have less but better. And so simplify to the point that you can still get dressed. Right. I think the worst thing we can do is over audit and then make it more hard on ourselves when we are going to get ready in the morning because we have nothing left.
C
Well, I think that's one of my fears, is that I'm going to get rid of stuff and then later think, oh, I could have used that.
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Or.
C
But I like your idea of replace because I think that then it's still there. And if I find myself wanting to use something like that but not wanting that piece of, then I know that I can just. I can use it in a pinch, but I can replace it.
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Exactly. Exactly. And I recommend putting those pieces in a whole separate section of your closet so you can notice how often you're reaching for them. And Then the pieces that you're taking out of there more often than the others, you're probably going to want to prioritize replacing with something better because it's something you're obviously really using.
C
Well, and what I'm running into now is I have so many things, and I made a challenge for myself that I would wear everything in my closet to figure out do I really like it or not. And having it actually on helps me decide sometimes. But I have so many things that I'm not wearing the stuff I really like very much because I have too much. And so it's kind of that balance of getting rid of some of the extra stuff that doesn't really completely work but is okay. And wearing the pieces I love more.
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Yes, yes. And that is where. Well, first of all, I love that challenge. Like, what a fun idea to do for yourself. And I bet you've come up with lots of new outfits that you have not worn before, which is always so fun. And, yeah, I think the closet audit flowchart will really help you figure out which things you can just let go of and be really confident in those decisions and feel good about that. And then again, you're probably going to put a lot of it in the replace category, and that's okay, because that's. That gives you some real tangible goals that you can start working on as you're shopping and planning for what you want to pick up for the season ahead. So I think it's just being a little bit slower and more strategic as you go through. And you know what, you might, down the line say, oh, I do kind of wish I kept that one piece. It might be a few months from now. It could be a few years from now. Sometimes I'll look back at a picture of something, and I'm like, why did I get rid of that thing? And, you know, you might have some nostalgia for it, but you can just celebrate that it worked for you at a time, and there's something better waiting for you. You can always go back and get something more updated that's similar to what you had if you do find yourself, you know, wanting it later on. But I think less is more to start. And, yeah, it sounds like you're doing a lot of the right things, so keep trying. Yeah. Yeah.
C
Well, you know, sometimes I feel bad, like, you know, each season I like to get a couple new pieces, and I feel kind of bad getting more stuff when I feel like I already have too much. But on the other hand, I don't want to. Yeah. I want to kind of freshen things up a little bit. So finding that, I feel like maybe I need to get rid of a couple more things so I have more space when I get new stuff that I actually can wear more.
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Yeah. Get rid of all the things that you're kind of dreading wearing in that challenge, the things that you're like. Yeah, I know. I told myself I have to wear this, but I don't really want to wear this. Right. You don't need to be feeling that way when we get dressed. You don't have to force yourself into those things. You can just acknowledge it worked at a time, and now you're. You're ready to move on from it. Yeah. And I. It. I think just being clear about what you do want to replace will really help you make some smarter shopping decisions in the months ahead too. So you'll. You'll know which things you're actually reaching for, but you want to update in some way, whether it's getting it in a better color for you, maybe a more updated silhouette, things like that. So, yeah, that's my best advice in terms of how to decide what to keep, what to restyle, and what to remove from your closet. And I know you had a couple other questions, and I think we have a few minutes if you want to.
C
Okay.
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Too.
C
Yes. And I think that part of it is the whole perfectionism, you know, like, every outfit's not going to hit all of the right buttons and to kind of, like, probably try to trust my instinct a little more than I have in the past and not do so much in my head. But one of my questions is, is I'm transitioning to gray to silver. My silver hair. And I don't know how that affects my colors. Like, my. The stylist, she also did my colors, and she had me as a soft summer, and I. That probably won't make a big difference with gray, but I don't know if maybe there's some colors that are maybe not so great anymore or what I should look out for.
A
Okay. Is that your natural color on the ends?
C
No, that's. No, my natural is brown, actually.
A
Okay.
C
And my hair is. My stylist made it blonder and blonder, so I wouldn't have as much of a demarcation, A more gradual brown. Yeah. Not a blonde. I don't like the blonde, but it allows me not to have super, super stark line. But I have a lot of kind of white and silver, so it is quite light. My natural hair color.
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Okay. And when you had your colors analyzed. What color did you have your hair?
C
It was a little bit darker than. Than this. It was a. A blonde kind of. Because she kept just moving me lighter and lighter as I.
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Sure, yeah. So, okay. So in general, when our hair turns gray, you might find that you start to look better in possibly cooler colors. But it sounds like you're. If she deemed you a summer, then you're probably already leaning towards cooler colors anyway. And then the only other thing that it is that it might soften your colors, you might look better in more muted tones versus or pastels versus like really bright or saturated colors or things that maybe you used to pull off a little bit easier. Not that you can't wear those, but you might find that you want to play up your makeup a little bit, maybe do a little bit of a bolder lip or a more dramatic blush or something like that, just so that you don't get lost behind those colors. So in general, I would say typically cooler. And then also it's going to be a little bit softer. The other thing is that it could make your overall contrast level a little bit lower as well. So if your hair used to be darker and now it's lighter, if your skin tone is also light, there's going to be less of the contrast between your overall colors. So those are the two, the three main things that are affected the temperature, the softness of the colors, and then your overall color contrast.
C
So how can I wear, like, I love the Burgundies that are coming out this in this chocolate brown, but I feel like the contrast is probably too much for me now. And. But how can I wear those colors without them being too, too bold for me?
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Yeah, I'm so glad you asked this because I want to clear this up for everyone. So having low contrast personal coloring doesn't mean that you have to wear light colors. Contrast is different than the depth of color. So contrast is the difference between the overall lightness and darkness. So let me explain this a little bit further. If you have low contrast, you have fair skin, fair eye color, and a light and light hair, then you don't have a lot of difference in lightness and darkness with your personal coloring. So all that means is that your outfit is probably going to look best if it also doesn't have a stark difference between lightness and darkness. Now, that said, and I'm in a similar bow, I have low contrast, medium low contrast. And so if I want to wear a dark top, you can't really see me, but I can kind of stand up for a second. I have a dark wash denim with this, so the contrast of my overall outfit is low because I'm not wearing a dark top with a very light bottom. So you could do all darker colors or you could do all lighter colors. What's going to overpower you a little bit is if you do light and dark together in one outfit.
C
So it's the contrast of the pieces within the outfit, not the contrast between my skin and the pieces.
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Exactly. Yes. That's going to open up a whole lot of possibilities for you.
C
Yeah.
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And really, it's just because if you're doing, let's say, a black and white outfit together, it's just going to be such a high contrast. And not to say that you can't pull it off, but people are probably going to notice your outfit before they notice you. My goal is I always want people to notice you, and then your outfit is like, a secondary complement to that. Right, okay. And that's really your personal goal. If you have a dramatic style and you're like, no, I want people to see this fabulous outfit that I'm wearing that's different. But ultimately, we want your. Your wardrobe to play up your best features, and so you'll probably feel most at home in clothing that is either all darker or all lighter or a little bit of a variation of that. So if you want to wear those chocolate browns and the Burgundies this season, I think just a subtle monochromatic would be really nice for you. If you did, like, a dark burgundy top with just a slight, like, maybe tint lighter skirt or pant or something like that, or vice versa. I think that would be so beautiful for you. And again, overpower you, because the con. The outfit in itself, is still low contrast.
C
Okay, well, that's good news.
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Yes.
C
Yeah, I was getting sad. I'd have to forego the burgundy and chocolate.
A
You wear those colors that you love and are excited about. That's one of my favorite ways to play with trends for the season, is just to bring in a couple colors that are going to work for me, and I think either of those would be really nice options for you too.
C
Super.
A
All right, I know we're a little over time, but I think you had one more question about your style. I'm okay to give you a couple more minutes if.
C
Yeah, well, I had a question about my style words, which I think this is something a lot of us struggle with. I did your style quiz, and I was clearly natural, and that one is. Works for me. And I like the Put together as the third word. But the second one, I'm not quite sure, because I think when I looked at your boards, that the classic. But classic to me, can lean preppy or. And that's not kind of what I'm going for. I don't know if contemporary. I mean, I don't want to. Yeah. And I think it's hard sometimes nail down that style word to kind of give me a little bit more guidance, as I'm sure.
A
Yeah, absolutely. Well, so the first thing is that there is variation to every style type, especially once you start combining them together. So, you know, there's different ways to interpret a classic style, especially once you start mixing other things, like natural elements, too. So it is important to make it your own. And I love that you want to come up with your own style words that feel really authentic and true for you and what you want to bring to your outfits. So I think maybe polished. Just hearing you could be a good one to kind of lean on. But what I would recommend, instead of starting with the words, it might be easier for you to build out a style mood board if you don't already have one. Get really clear on the visual side of things and what you like. And then I also recommend going through your wardrobe and pulling out the top 10 pieces that you love the most. And then after you pull out those pieces, ask yourself what it is that you love about them and try to pinpoint your style values. It could be versatility. It could be comfort. It could be maybe something about the fit. If it has kind of a tailored look to it that you love, Try to figure out what the values are that draw you to those particular pieces in your wardrobe. And then from there, I think if you look at your style mood board, start to notice any recurring themes. Look at your favorite pieces that you have right now. Look at the recurring themes. I think that will help give you a better selection of words that you can then hone in on. And that'll also give you some more directives as you're shopping, too. I always have my style mood board and my colors up when I'm shopping online so that I can reference things and make sure it's going to fit in with my goals, that I don't get distracted by shiny object syndrome, and that I'm really thinking about what is most important for me when I'm shopping.
C
Super. Yeah. Because.
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Yeah. So I kind of reverse engineer the words. Maybe don't start with that if you're getting stuck.
C
Yeah, yeah. Because I think sometimes if they're too broad. Like classic is a very broad category that it kind of makes me float. But that's a good idea to start at the back rather than at the front. So.
A
Yeah. Yeah. Especially if you're getting stuck, just try something else and then I think it'll be more clear to you which words are going to fit with all of those. Those things that you've kind of pulled out from that super. All right, Meg, this was.
C
Well, thank you so much, Heather. So I really love hanging out with you.
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I'm glad we could get through all of your questions and if you have more, then you go ahead and bring them to the Wardrobe Revamp Boot Camp because we're going to do a little Q A time every day and then also in our Friday session, we'll have a full hour to tackle everything else that you need.
C
Well, thank you so much for your time. I really appreciate. I'm looking forward to the Bootcamp.
A
Yes, I can't wait to see you there.
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Thank you for listening to today's episode. If you want to stop copying everyone else's style and start dialing in your own spoon worthy signature look, head over to take my free 5 minute personal style quiz which you can find at the link in the show notes. If you've enjoyed our time together, please be sure to rate, review and subscribe to her style podcast so you never miss an episode. Finally, I invite you to make this a two way conversation and send me a DM over on Instagram eatherigstyle to let me know how I can best support you on your style journey. I'm always here for you in style and service. Until next time.
Episode 269 | When to Get Rid of Something and When to Try Harder to Style It [LIVE Coaching!]
Host: Heather Riggs
Date: September 1, 2025
Guest: Meg (Live Coaching Session Winner)
This episode features a live coaching session with Meg, a member of Heather's community and the recent winner of a Wardrobe Revamp Bootcamp prize. Together, they tackle some of the most common wardrobe struggles:
Heather delivers practical, compassionate advice for anyone who feels stuck with a closet full of clothes that just don't feel right.
Meg describes her style journey since turning 50 and feeling disconnected from clothes she previously bought.
“It might feel a little frustrating when you look at your clothing, and it’s not completely matching up the way that you want, but it’s good to recognize that, and now you can feel empowered to start making some shifts.” – Heather (03:46)
“It’s progress over perfection... give yourself permission to fall in love with the process and to enjoy taking it one little baby step at a time.” – Heather (05:16)
“You don’t need to remove [frustrating pieces] from your wardrobe, but you might want to gradually replace over time… not like keep or let go – it's keep, replace, maybe repair or alter, or remove.” – Heather (07:55)
“You never want to work too hard to feel good in your clothing. So if you’re trying to make something work and it’s just not working... I think you can feel okay about letting it go and moving on to better things.” – Heather (10:00)
“It’s always better to have less items that you really love than a lot of things you’re not excited to wear.” – Heather (10:25)
“Put those pieces in a whole separate section of your closet so you can notice how often you’re reaching for them.” – Heather (11:30)
“Get rid of all the things that you’re kind of dreading wearing in that challenge... You don’t have to force yourself into those things.” – Heather (13:59)
“You might look better in more muted tones or pastels… and your overall contrast level a little bit lower as well.” – Heather (16:00)
“Contrast is different than the depth of color… If you have low contrast, your outfit is probably going to look best if it also doesn’t have a stark difference between lightness and darkness.” – Heather (17:19)
“If you want to wear chocolate browns and burgundies… a subtle monochromatic would be nice… it won’t overpower you.” – Heather (19:30)
“There’s variation to every style type…try to pinpoint your style values. It could be versatility, comfort… maybe something about the fit.” – Heather (21:00)
“Reverse engineer the words—maybe don’t start with that if you’re getting stuck.” – Heather (22:28)
This power-packed coaching session delivers practical, empathetic guidance for anyone navigating the confusing “should it stay or should it go?” phase of their style journey. Heather’s patient, systems-based approach makes the daunting process of revamping your wardrobe both accessible and a little more joyful.