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Have you ever bought something you were really excited about? You saw it, you loved it, it felt like such a good find, and then it just never became part of your regular outfits. Maybe you wore it once, maybe it's still sitting in your closet with the tags on, or maybe every time you try to style it, it just doesn't come together the way you thought it would. And it's confusing because nothing about the piece itself seems wrong. It's cute, it fits, it looked great in the store or online. So what happened? I that's what I want to talk about today because this is one of the biggest disconnects I see when it comes to shopping and building a wardrobe you love. We tend to assume that if we like something, it should work. But liking something and using something in your real everyday outfits are two very different things. So in this episode, I'm going to help you close that gap. We're going to shift the way you evaluate pieces before you buy them, and I'm going to walk you through five simple questions you can ask yourself to predict whether something is actually going to become a valuable asset to your wardrobe, or if it's just going to be another piece that that winds up being a regret. Let's save you from future shopping snafus, my friend, and make sure your wardrobe investments truly earn their place.
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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, Heather 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. Now. At some point in that cycle that I know we've all experienced, there's a moment where you look at something in your closet and you're like, okay, why did I even buy this? And I know it's easy to jump to, that was a bad purchase or why did I pick this up? I shouldn't have gotten this and kind of beating yourself up a little bit. But I think there's a much more helpful way to look at it. It's not that it was a bad piece and you have amazing taste. You're not going to pick up something that's not going to serve you at all in any season for any reason. It just wasn't the right long term piece for you. Whether you wore it, whether it's still sitting there with the tags on, there was something that compelled you to pick it up. So you want to lean in and look at, okay, what was working about this thing, while also recognizing it, was maybe not the best investment for your wardrobe overall. And once you understand that, I really think everything can start to shift. Because now it's not about being more disciplined or having better taste. Like I said, it's about asking better questions before you buy. Most of the time, we're just not pausing to do that. Especially when something feels exciting in the moment and you're kind of lured into it and excited about the idea. And it's easy to get caught up in how something looks or how it could fit into your life and to skip over the part of evaluating whether it actually will. So this simple shift that I want you to make today is this. Instead of just asking, do I like this? Start asking, will this actually make sense once it's in my closet? Because your wardrobe isn't just a collection of individual pieces. It's something that you have to use and rely on every single day. It has to function on your real average mornings with your typical schedule, and, of course, with the clothes that you already own. And if something doesn't fit into that, it's probably not going to become a go to, no matter how much you liked it when you bought it. Now, as I said in the intro, I have five questions that are really going to help you to kind of set up the right criteria for figuring out whether something is a good long term investment. But before we dive into those, I do want to set up one quick baseline. So for the rest of this episode, we are going to assume that the piece that's in question has already passed your style foundations test, meaning that it aligns with your personal style, it works for your body and the fits that you feel best in. So it flatters you, and it's in a color that lights you up, that integrates well with the other hues in your wardrobe. Ideally, it is in harmony with your personal color palette, if you have one. So we want to make sure that it checks those three boxes first. If not, it might already be a no for you. So in that case, you don't need to overthink it. You know, it's not going to work well for you if it doesn't fit your style, work for your body and flatter your complexion. Right? So even when something does meet those criteria, this is where a lot of women can still get stuck. This is where you can end up with pieces that technically should be a good choice. Maybe they fit with all of those foundations, but they don't end up getting worn. And it's because there's A disconnect between that piece and what's in your closet or on your calendar. So these next five questions are going to help you to take this evaluation process a step further. Before you buy something, this is how you can start to predict whether something will actually earn its place in your wardrobe. All right, so if you want, grab a pen, get ready to take some notes. The first question that I want you to ask is, can I clearly see where this fits into my real life? And I encourage you to be specific here. Not, this could be cute for brunch, or I could wear this out at some point. But can you actually picture yourself reaching for this in a real situation that you have scheduled, something that's coming up? Because if it's a little vague or you're kind of stretching to come up with a scenario that is rather unlikely, that's usually a sign that it's not going to be as practical as you might be thinking in the moment. And those are the pieces that tend to stay in your closet, waiting for the right time instead of becoming a seamless part of your regular rotation. All right, the second question. Can I style this multiple ways with what I already own? This is where you bring it back to your current wardrobe. Not things that you might buy later or items that are on your shopping list. Not what would make it feel complete eventually, but what can you pair it with right now? Can you think of at least two or three outfits using pieces you already have? This is where it's super helpful if you have a digital inventory of what's in your closet. So if you're out at a store shopping or even if you're browsing things online, you can be looking at your real wardrobe and try to kind of mix and match things visually and see what might work well together to create multiple outfits from that one piece. Because if your brain immediately goes to, well, I could get this, and it might work with this piece or that piece, but I would definitely need to buy some different shoes or I don't really have the right jacket for this. That is very important information, and it doesn't necessarily mean you can never buy this thing, but it does mean it's not going to be an easy addition to your wardrobe. Right now. The pieces that you end up wearing the most are usually the ones that just pop in quickly. They don't require a whole new plan. They don't require additional pieces to make them work. They just blend with what you already have. You can grab and go. Everything's easy peasy. Okay, friend your third Question is, is this in line with how I usually put outfits together? This is a subtle distinction from your personal style and even the first question that we talked about of how it fits in with your life. But this one addresses the g between how you want to look and feel and how you actually want to look and feel. Like I want to want to look this way, but when I go to get dressed in the morning, I typically always reach for this type of thing instead. And it's not that it either or isn't aligned with your style preferences and your goals. It's just what's most practical for you on your average morning. I know it's very easy to buy for the version of yourself that wants to feel a little bit more elevated or look more polished or just different from how you typically show up. And it might feel like a great match for your style, but it's not a great match for what you want to wear on your typical day. So if your day to day life leans a lot more casual or more practical, maybe you are taking care of your kids all the time or you're more on the go and the piece that you're considering doesn't really align with that, you're probably not going to reach for it very often. Even if you have the right occasions on your calendar, even if you could visualize yourself wearing that thing. I want you to get so honest with yourself. Is it something that you are going to be excited to reach for or is it maybe a little bit too outside your comfort zone? Your wardrobe should support your current habits, not rely on you becoming a different version of yourself overnight. And yes, your style can and will evolve, but it still has to meet you where you are right now in order to function right? We don't want to end up with those pieces that fit your style goals on paper, that work for the events on your calendar, but still don't get worn because they're not completely and totally you or maybe even the most comfortable thing in the moment, right? So think about that realistic gap that sometimes sneaks up on us because again, it looks great on paper, but there's just some reason underneath that it is not working for you. This could be where that disconnect is really falling. So please get real with yourself about if it's something that you're going to be excited to reach for. And on a similar vein, the fourth question for you is, will I still be excited to wear this after the first few times? Right? I don't want you to just reach for it once. We want to reach for this thing again and again. Not to the point that we get sick of it necessarily, but you do want to maximize your investments. And I know again, some pieces feel exciting in the moment because it's something new or different, but that feeling doesn't always last. I'm actually going to do a whole podcast episode on this soon because I know it's such a big thing for a lot of us. I hear all the time from women in our community that there's nothing wrong with what you have, you're just bored with it. And so instead of asking do I love this right now? I want you to ask, am I going to continue to love it? Can I see myself reaching for this once the novelty wears off? I know sometimes it's hard to predict the future and how you're going to feel about things in several months or even a couple of years from now, but it is helpful to think about this at the start. This can help you be a lot more strategic with what trend pieces you pick up as well, especially if you're talking about investment items. A couple of other follow ups to this, not to give you a whole other list of questions, but just to kind of get you thinking about this one is will I still like it in a few weeks? Does it feel like me? Or is it just something fun and different? Is this something that I could see myself repeating? Or is it just something that I kind of want to play with and maybe try once? In that case, you know, I'm a big fan of renting pieces, especially if it is for a special occasion or if it's a trend piece that you just kind of want to dabble with but you don't want to make the long term investment in it. And then also loosely related but equally important, does this feel like a piece I can rely on? This could be a whole other question in and of itself, but I think it kind of fits in with the umbrella of will I be excited to wear it after the first few times? Is it something that doesn't just look good, but it's going to hold up, it's going to feel great, and it's going to wear well time and again. So we kind of want to think about the color quality and also whether you're going to get tired of it more quickly. All right, and the fifth and final question is will this make getting dressed easier or more complicated? And this is one of the most helpful filters that you can use. The pieces that you reach for again and again tend to make your outfits feel more Obvious. You don't have to overthink them. They pair easily, they're reliable, and they simplify your decisions and your mornings. The ones that don't get worn as often usually come with a little element of friction. You like them, but they take some effort. They don't quite come together without some extra thought, right? You've got to do some styling tricks to make it work, or you always have to pair it with this other thing in order for it to look good on you. And over time, you're going to eventually stop reaching for it. Not because you don't like it or it doesn't work, but because it's just not easy. It always takes a little extra prep, a little more planning. I know for me, sometimes I will second guess if I know I'm going to have to steam something every time I want to wear it right, or if it's like a dry clean only piece and it's going to have to go out to the cleaners. And so a really simple way to think about this is, is this piece going to make my mornings and my life easier or is it going to give me one more thing to figure out? Because your wardrobe should be reducing decision fatigue, not adding to it. And of course, I'm not saying don't ever iron your clothes or you don't buy things just because of the fabric, but it is really practical to consider. And this might be lighting up some aha moments for you of why you haven't been reaching for some of the pieces that you actually were really excited about when you bought. So again, just to recap, before you buy something, the next time you go shopping, I want you to ask yourself, where does this fit in my real life? Like specific situations, specific moments where you'd reach for it. Make sure that you can think of at least a few coming up on your calendar. Secondly, how will I wear it with what I already own? Does it integrate seamlessly with your existing pieces? Number three, is this in line with how I usually put outfits together? Not on your best day. Not when you're trying really hard. But your default number four, will I still be excited to wear this after the first few times? And number five, does it make my outfits easier or more complicated? And what you'll start to notice is that when you run pieces through this kind of filter, your decisions are going to feel a lot clearer. You are going to have some immediate nos that have normally been a big yes. You're not relying on that in the moment excitement as much. You're bringing practicality into it. I know it might feel a little less fun, but you will be grateful when your wardrobe is working cohesively and you have what you need. When you go to get dressed every day, you're not bringing things home and just hoping that they're going to click together. You're choosing things that already make sense. And that's really the goal. Not to have a closet full of stuff that you love in theory, but to have a closet full of things that you actually wear in your day to day life that make you feel your best. Because those two things are not always the same. And once you start choosing pieces that really fit into your wardrobe and your life not just stand out on their own, that is when everything will start to really come together. Getting dressed will feel easier, your outfits are going to look more like you, and your shopping is of course going to become a lot more intentional. I know that's something you want. That's. That's probably why you found yourself. And that is of course exactly the kind of shift that we focus on together inside Her Style Collective where we go deeper into helping you define your style, understanding what actually fits your life, and building a wardrobe where everything connects. If you're interested in finding out more about my group coaching program, you can head to herstylellc.com collective. I just want you to not be constantly second guessing your choices or trying to figure it out every single time you shop or being a little bit mindless and just bringing home those cute pieces and not really thinking about the long term use and whether it's going to serve your wardrobe and your life in a bigger way. You already have that clarity. Until then, just start here. Use these questions the next time you shop. Before you buy something, just pause for a second and make sure that it really is going to earn its place in your wardrobe. That one small shift can change so much for you friend. Thanks for joining me today and I'll meet you back here next week for our next episode.
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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 swoon 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 eatherriggstyle 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.
Her Style Podcast | Episode 319
How to Tell If Something Will Actually Work In Your Wardrobe (Before You Buy It)
Host: Heather Riggs
Date: March 17, 2026
In this episode, Heather Riggs tackles one of the most common challenges faced by women striving for an intentional, cohesive wardrobe: why do we buy pieces we love—only to barely wear them? She unpacks the reasons behind these “wardrobe orphans” and empowers listeners to make smarter, more strategic shopping decisions. Heather shares her five-question framework to help you predict if a new item will earn its place in your closet, making getting dressed easier and keeping closet clutter at bay. The episode blends practical wardrobe strategy with Heather’s signature supportive, down-to-earth style.
Impulse Buys vs. Real-Life Wear: Many women buy items they love in-store or online, only to find those pieces languishing unworn. Heather normalizes this struggle, explaining that the issue is rarely about “bad taste”—instead, we often skip crucial evaluation steps.
Purpose of the Episode:
Heather’s central framework for vetting new purchases consists of five strategic questions. She pauses to explain the purpose, nuances, and practical application of each:
[05:35]
“Can you actually picture yourself reaching for this in a real situation you have scheduled?... That’s usually a sign that it’s not going to be as practical as you might be thinking.” (06:10)
[07:25]
“Not what would make it feel complete eventually, but what can you pair it with right now? ... The pieces that you end up wearing the most are usually the ones that just pop in quickly.” (08:00)
[09:30]
“Your wardrobe should support your current habits, not rely on you becoming a different version of yourself overnight.” (10:50) “It looks great on paper... but there’s just some reason underneath that it is not working for you.” (12:05)
[12:30]
“Can I see myself reaching for this once the novelty wears off?... Is it just something fun and different?” (13:00)
[14:40]
“A really simple way to think about this: is this piece going to make my mornings and my life easier or is it going to give me one more thing to figure out?” (15:00) “Your wardrobe should be reducing decision fatigue, not adding to it.” (15:15)
Review the Five Questions Before Every Purchase:
Clarity Beats Excitement:
“Not to have a closet full of stuff that you love in theory, but to have a closet full of things that you actually wear in your day to day life that make you feel your best. Because those two things are not always the same.” (16:25)
Heather emphasizes that intentional style is about aligning your wardrobe with your real life—not just your dream self or fleeting trends. Her warm, practical approach gives listeners confidence and concrete strategy to escape the cycle of impulse buys and wardrobe regret. Try these questions for yourself, and notice how much easier and more satisfying your everyday style becomes.