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At Her Style Podcast, we talk a lot about making your wardrobe work for your real life, and I stand by that. It's important to have pieces that fit effortlessly into your everyday outfits, but don't take that to mean you can't or shouldn't wear the beautiful and sometimes impractical items you love. In this episode, we're talking about how to integrate your nicer clothes into even your most laid back and casual weeks because life is too short to save all of your favorites for those rare special occasions. I also believe getting dressed gets to be fun and there is a way to infuse your personal style. Even if your life has become much more casual, it's totally possible to wear even some of your fanciest pieces without feeling overdressed. So let's dive in and discuss in today's episode.
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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. Welcome back friend. Today we are tackling the problem. Okay, wait, can we really call it a problem of having too many pretty clothes you never actually get to wear? Maybe some of them still have the tags on or they were for a previous season in your life when you worked in an office five days a week, or maybe before you had kids, or just when the world required getting dressed up on a more regular basis. Everything has become much more casual in our society and so you might be feeling like the wardrobe that you used to have and love, or maybe the style that you aspire to just doesn't really fit in with what you actually have going on on your calendar. I know I'm not the only one who spends most of my time at very casual events or working from home. Right now we're in the throes of sports season, so you can typically find me at the baseball or lacrosse fields or just getting things done around the house, or going for family walks with the puppy and maybe meeting at a friend's house for a laid back dinner. This is not my most glamorous stage of life, but I love it and I still love getting dressed up whenever I can. Maybe you feel the same way. In fact, I was just talking with a podcast listener this past week and she mentioned that she's drawn to elegant, slightly dramatic dressing, but that that type of look only fits with about 20% of her life and I could so Relate to this. I would probably dress quite differently if my life was different, and you might feel the same way. And I've definitely seen this frustrating pattern where you have clothes in your closet that you love, but you don't wear them. And it's not because they don't work for you and they're not flattering, but it's because they don't feel like they fit with your everyday life. So in this episode, I wanna show you how to break that pattern. How to wear the pieces that you love, even if they feel like they're a little bit too much, and how to do it with confidence and in a way that does actually work for your typical day. Let's start with what's actually going on here, because it's probably not what you think. Most of the time, we assume the issue is that our clothes are too dressy or just not practical enough. But I don't think that's usually the problem. I think the problem is that you've accidentally separated your wardrobe into distinct categories. You've got your dressy clothes, the ones that you love, the ones that feel like your personal style, the ones that you would wear if you were going somewhere or if you had more dramatic occasions going on on your calendar. And then you've got your everyday clothes, the easy things, the comfortable stuff, the pieces that are a little bit simpler or that you default to more regularly. And. And to be clear, my hope is that you love them too, right? The goal is to build a wardrobe that you love in every which way. But what I see is that over time, those two categories can start to drift further and further apart, right? So you've got your dressy, special occasion clothes, and then you've got your everyday clothes. And that can mean that sometimes your daily outfits start to feel a little bit flat or repetitive. They're kind of watered down. They feel a little bit less like you or like the version of you that you want to be seen as. And then your favorite pieces, the fun and seemingly impractical items, just sit there waiting for a moment that doesn't come around very often. That is the gap that I really want to help you close today. Now let's talk about why this happens. I think first, your environment matters more than you think. And if you're home most of the day, or you're running casual errands, or you're just not around a lot of people who are dressed up, anything that's slightly elevated can feel like it stands out. And even if the outfit looks great, it can Feel like it doesn't quite match what's going on around you. Second, you've probably trained yourself to associate certain pieces with specific occasions. So maybe you only wear your wrap dress out to dinner and you have a pair of shoes that make you so happy, but they're only for formal events. Or you have the gorgeous suit, but you can only wear it when you have board meetings going on at your office. So you have these pieces that you kind of only save for certain occasions. And then when you try to wear them on a random weekday, your brain is like, wait a second, something's not right here. This feels too risky. And you get nervous and you dial it back. And often there's this subtle comparison that happens whether you realize it or not. You might look at your outfit and then you think about what everyone else might be wearing or what you usually wear in that situation. And suddenly you worry that you're going to look like you're trying too hard or you're going to be out of place or you're going to get too much attention and not in a good way. And I know how awkward that can feel. I don't honestly remember if I shared this story on the podcast before. I know I sent it in an email many moons ago, but I will tell you again. Anyway, I one time wore this midi length bodycon dress and it was elegant, it was, you know, not alluring. That's not really my style. But it was just this really fitted turquoise dress and I put on sky high stilettos, what I used to wear all the time. And I wore this to what turned out to be a very casual luau themed wedding rehearsal, most of which took place outside on rough garden terrain. So. So not only did I look insanely overdressed, it was really hard to navigate my shoes and my outfit, and it wasn't intentional at all. My sweet husband, who was in the wedding party, forgot that there was a luau theme. So I didn't get the memo about that. And yes, I felt absolutely ridiculous. I was totally overdressed. I just had to roll with it because what else are you gonna do, right? But that's kind of an extreme example to say I don't like getting that kind of attention either. I know how it feel when all eyes are on you, like, what is she wearing? Why is she wearing that? And that's definitely not what we're going for. But let's imagine in your typical scenario, you know what you're actually going to do. You know what the tone of that event is. Going to be, even if it's just running out to the grocery store and instead of adjusting the outfit a little bit, you just change out of it completely. And I don't know if that's totally necessary. I think Instead of saving all of your nicer clothes for the formal wedding rehearsal, let's talk about how you can integrate them in a thoughtful and still very realistic way. And this is where I just want you to simplify everything. Because the easiest way to make your nicer clothes feel more wearable is to stop trying to build an entire outfit around them. Instead, I want you to focus on just one elevated piece at a time. That's it. One piece that feels a little bit more up leveled, maybe a little more dramatic or a touch of alluring or somewhat elegant, A little bit more like the version of your style that you love, or the aspect of your style that you feel like you've been having to tone down too often. And then you can build the rest of your outfit in a way that feels easy and grounded and perfect for your everyday. So let me give you some examples of this. Instead of wearing a dress with more polished shoes and accessories and feeling like you have to find the right occasion to wear it, you might wear that same dress with something more casual, like a pair of sandals or flats and a denim jacket. Things that make it just feel more everyday, more low key. Or instead of saving your nicer tops for when you're going to go out, you pair them with your everyday jeans and just wear them to your kids school pickup for the day and feel amazing. When everything in your outfit is elevated, it can feel like too much, but when one piece is elevated, it starts to feel more intentional and it can be executed in a way that pushes you just a teensy bit outside your casual comfort zone rather than feeling too over the top. In a similar vein, it might not be the piece itself that feels too dressy, it might just be the way that you typically style it. I have definitely shared this story before, but it always reminds me of my sweet client Isabel, who had this professional black blazer that she never wore because it was something she felt like she was supposed to have but it didn't fit with her casual life. I actually had interview Isabelle on the podcast for an interview not too long ago, so I'll link her story up in the show notes too if you want to hear this from her directly. But she was never wearing this blazer and she wasn't sure if she should get rid of it until she tried it on with A whole bunch of unexpected items in her wardrobe. She tried wearing it over a sexier dress for a date night. She tried pairing it with denim shorts and a baseball hat for a cool weekend look. And suddenly it became one of her favorite go to pieces just because she was willing to try it with different things and see what could work. And I guarantee there are so many ways to take those fancy pieces that you've been saving and just make some small adjustments to make them work for your typical day. Now, shoes are probably the biggest one. I think you can take the exact same outfit and completely change how it feels just by switching the shoes. Hair and makeup also play an important role here. I've talked a lot about finishing touches, which can help to elevate your casual pieces. But you can also do the flip side of that and style things in a more casual way to make your dressier pieces feel a bit more approachable. Layers are another easy way to adjust the feel of your outfit. Adding something simple or relaxed can take the edge off of a piece that feels more dressed up all on its own. So if everything in your outfit feels very done, very polished, very, very put together, it can push the outfit into that over the top or too much category. But when things feel a little more relaxed, the whole look comes down a level without losing your style. In fact, if I. I'm just thinking now, if I had worn that same exact midi dress to that luau with a flat shoe or even a subtle kitten heel, and if I had known the theme and had played it up with some tropical inspired jewelry or even just a lei, it would have absolutely worked better for occasion. So if it helps loosen things up a little bit, maybe try pushing up your sleeves or do a casual tuck. Keep something slightly undone so it doesn't feel like an overly effortful outfit. So instead of thinking, okay, this just does not work for my real life, I want you to start asking, how could I make this work for my real life? What would make this piece feel easier to wear? I love taking an item and searching for ways to wear it. On Pinterest, you could type in casual weekend outfits with a sequin blouse or sports mom midi dress outfits and then just see what ideas come up. It might not be things that resonate for you, but you might be really inspired and you might realize you have some pieces in your closet that you could put together to make it work. Or just get your little booty into the closet and start playing dress up like Isabel did. You might be surprised at what combinations you can come up with that will work for way more occasions than you would have expected. So bottom line, don't be afraid to try things. And I will say, if your best pieces are going unworn and your everyday outfits feel like they're missing something, at some point you have to decide that your normal life is enough reason to wear them. You're getting dressed anyway, friends, so you might as well have some fun and enjoy what you're wearing. And don't be afraid to play outside the box to do something a little bit different, to be the dressiest one in the room. And here's what I want you to do this week. I want you to pick one piece in your closet that you love, but you don't wear very often because it feels a little too nice for your day. Just one piece. And sometime this week, I want you to wear it on a completely normal day. Don't overthink it. Don't try to make it perfect. Just adjust the rest of your outfit so that it feels easy and go on with your life. Embrace it. Wear it with confidence and notice how it feels. Because most of the time, the thing that feels too much at first or in our minds ends up feeling exactly right. Once you actually wear it, you might feel more like yourself. You might be excited to be infusing new parts of your personal style preferences. And I do want to give you some caveats to this, because if you're still thinking, okay, but what if I do this? What if I have my outfit and I still feel really awkward or overdressed? So I'm going to give you a couple of quick things that you can check before you change your entire outfit. So the first thing is to think about the fabric. Sometimes it might not be the piece itself. It's just the material that's making it feel dressy. So if something feels like too much, you might want to be more conscious about pairing it with clothing that's softer or more relaxed to balance it out. Like I had mentioned, if you were looking for ways to wear a sequin T shirt, maybe you're going to tone it down with an easy, very casual pair of joggers or jeans and even a sneaker. Like, you're going to want to really go heavy on toning down the rest of your look to soften everything. You can also do a quick reality check. Are you actually overdressed? Or are you just more dressed than you're used to? Because those are two very different things. And a lot of time it just feels unfamiliar, but it's not actually wrong or too much so. You might want to raise the bar a little bit on your own expectations and be willing to just take tiny baby steps outside your comfort zone. You might not be as overdressed as you think you are just because it feels different than what you would typically wear. And if it still feels like a big jump, yes, scale it back. You don't have to go from your most casual outfit straight into something fully styled. Just move one step up and let yourself get comfortable there. Maybe start by taking your usual everyday uniform and adding a beautiful handbag or a fun piece of jewelry that you typically save for special occasions, not both. Just pick one thing and finally give yourself a little time to adjust. Maybe you're going to wear this around the house or on a low key day when you're not going to see anyone and let it start to become more normal for you. The more you actually wear your clothes in real life, the less they'll feel like they need a special reason. If you've been stuck in that cycle where your everyday outfits feel a little underwhelming and your favorite clothes are sitting in your closet waiting for the right moment, this is your reminder that you don't need a different wardrobe or a more exciting social calendar. You just need to start dressing a little differently and infusing the items you love into the everyday outfits you wear. You don't have to save your style for later. You can bring it into your week exactly as it is now. I hope this episode opened up some new possibilities for you and if you enjoyed this or if you've been binge listening to these episodes and you're loving the show. It would mean so much to me if you would take just a minute to leave a written review on Apple Podcasts or wherever you like to listen. It really is the best way to let me know what's resonating with you and to help other women find our community. For now, friend, enjoy your week, have fun getting dressed and wear something a little fancier today if you feel so inclined. It's going to be very cold at my son's baseball game tonight, but I just might try to do the same myself.
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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 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.
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Until next time, Sam.
Her Style Podcast Episode 324:
How to Wear Your 'Nicer' Clothes During the Day Without Feeling Overdressed
Host: Heather Riggs | April 21, 2026
In this empowering episode, Heather Riggs addresses a common frustration among women: owning beautiful, dressier clothing that rarely gets worn because daily life doesn’t seem to call for it. She challenges the idea of saving “nicer” pieces for special occasions and offers practical, confidence-building strategies to wear and enjoy them in everyday settings—without feeling overdressed or out of place. The episode blends style psychology with actionable wardrobe advice, encouraging listeners to break free from rigid clothing categories and embrace a more intentional, joyful approach to personal style.
On Wardrobe Categories:
“Over time, those two categories can start to drift further and further apart… and that can mean sometimes your daily outfits start to feel a little bit flat or repetitive. … And then your favorite pieces, the fun and seemingly impractical items, just sit there waiting for a moment that doesn’t come around very often.”
– Heather (03:35)
On Social Pressure:
“You worry that you’re going to look like you’re trying too hard, out of place, or get too much attention—and not in a good way. And I know how awkward that can feel.”
– Heather (05:30)
On Integrating Dressy Pieces:
“When everything in your outfit is elevated, it can feel like too much, but when one piece is elevated, it starts to feel more intentional…”
– Heather (10:55)
On Experimenting:
“Get your little booty into the closet and start playing dress up like Isabel did.”
– Heather (14:20)
On Redefining What’s ‘Overdressed’:
“Are you actually overdressed, or are you just more dressed than you’re used to? Because those are two very different things.”
– Heather (16:00)
Heather encourages women to let go of arbitrary styling rules, blur the lines between “special” and “everyday,” and wear the clothing that makes them feel most alive—now, not later. Listeners are reminded that life itself is worth dressing up for, and style should be a creative form of self-expression rather than a rigid set of dos and don’ts.
“You don’t have to save your style for later. You can bring it into your week, exactly as it is now.” – Heather Riggs (16:30)