Jennifer Mackey (0:00)

To quote Heidi Kluman, Project Runway in fashion, one day you're in and the next day you're out. But we all know it's not quite that simple. Styles don't go from looking current and on trend one day or even one season to completely looking out of style the next. Most of the time, it takes quite a while before things actually look dated, and often it happens so slowly that we don't even realize it. But if you've got a little feeling that your look isn't looking so current, I'm here to help. Over the course of the next two episodes, I'm going to share how to turn the style ship around and stop looking dated. Let's get started. Hello gorgeous. Welcome back. Welcome back to the Everyday Style School, the podcast that gives real life style advice to real life women. I'm your host, Jennifer Mackey. Mary I'm a wardrobe stylist who's been dressing everyday Women for over 25 years. And I'm the founder of Everyday Style where we are on a mission to inspire women to love the way they look and give you the tools to make getting dressed easy. One thing I have said a million times over the years is that a great wardrobe is as much about what you take out as what you put in. Yes, it is important to put the right things into your closet, things that fit and flatter and make you feel amazing. But it's just as important to get rid of things that don't fit, that don't flatter, and that don't make you feel good. That clutter or closet noise as I like to call it, makes it hard to see what you have and what you need. And it makes it really difficult to get dressed each morning. And it's the same thing with current or trendy or on trend items, whatever you want to call them. Every three months I do an episode sharing what's trending for this season. And every three months I know you're listening and I know that you are adding these things to your wardrobe and that is wonderful. But how often are you pulling things out of your closet that are no longer looking current? If you're like most women, it probably doesn't happen that frequently. Over time, just adding and not culling will leave you with a wardrobe that even though you're putting in on trend items, doesn't look current and dare I say, looks a little dated. So over the next two episodes, we're going to talk about looking more current without necessarily buying a ton of stuff. If you feel you need or Want to freshen your wardrobe with a few pieces? Great. But I really want you to focus on your current wardrobe, what you have right now, what you're wearing, and how you're wearing it before you just start shopping. In today's episode, we're going to talk about what it means to be current versus trendy versus dated, why looking current matters, and how to be more aware of what looks current or what looks dated. We're also going to talk about dated styling. And then in the next episode, I'm going to share 10 dated styles. And I know before we get started that over the next couple of weeks, some feelings are going to get hurt. I am going to ruffle some feathers. I'm going to say some things you might not want to hear. I'm going to describe some things you might be wearing at the moment, and you might want to argue with me about it. So let me say super clearly, wear what you like. If you love it, wear it. These episodes are for women who don't want to look dated, but aren't sure or don't know if they do. Some people are wearing dated things because they love them. Others are wearing dated things because they don't know any different. My advice is for that second group. If you're in that first group, be happy. Wear what you love. That's the whole point. And, you know, it's funny, when I do episodes like this, I always get my own thoughts together. And then I like to see what other creators are saying on the subject. I want to make sure that I haven't missed anything really important. And I also want to make sure that I'm bringing something new to the discussion and not just repeating what everyone else is saying. In every video I watched on this topic, the creator said some version of if you love it, wear it. Take what works for you and leave the rest. I'm not saying you can't wear these things. All these things that I know you've heard before because I've said them a million times. But then in every single comment section, there was at least one person saying, I don't care what you think. I love my whatever. And going to keep wearing it. You don't have to follow the trends. Just really having a moment and it's like, great, do that. That's the entire point. That's what all of us are saying. The fact that something is dated doesn't mean you have to stop liking it or wearing it. But on the other hand, just because you're liking or wearing it, it doesn't mean it's not dated. My job in these episodes is to tell you what what looks current right now, April 2025, and what doesn't. And your job is to decide what to do with that information. But again, you are listening to a style podcast and part of style is talking about what's in style and what isn't. So please, over the next two episodes, if I describe exactly what you're wearing and how you're wearing it, please remember this isn't personal. This is just information you can choose to do something with or or not. It's totally up to you. I want to start with why this matters, because it isn't about constantly buying new clothes and wearing all the latest trends. But the truth is, your style is often one of the first things people notice about you. And first impressions matter. Looking dated can influence people's perceptions of you, and you can be perceived as being out of touch. Wearing more current styles indicates that you are engaged in the present moment, that you're aware of cultural shifts, and that you are adaptable and can change with the times, especially in professional settings. This can be important because you don't want people to look at you and think that you are stuck in the past or irrelevant or inflexible. And the second reason might sound a little shallow, but dated equals old. Before you grab your pitchfork and start writing me a strongly worded email, I am not one of those people who believes that the primary goal of a woman's life should be staying young. Not at all. I don't believe that we should put all of our efforts into looking 20 years younger. I think that is exhausting. No, thank you. But I've also never met a woman, and I have met a lot of women who says, yes, I would love to look decades older than I am. But that's what's happening and a lot of women don't realize it. So maybe instead of fillers and facelifts, we could just like update our jeans and shoes. That seems like a reasonable, happy medium. And I always used to say to my clients, it's not about looking young, it's about looking youthful. I don't care how old I am, how old I get. I always want to have a spirit that is youthful and that can show up in your wardrobe as well. Over the years, I have worked with countless women who didn't want to be trendy because they associated that with trying to look young. But in their efforts to avoid anything new and different and on trend, they ended up looking older. In large part because their wardrobes were dated. And I think it's important to understand and acknowledge that there is a lot of space between trendy and dated. And this is where a lot of us get off track. So really, the first thing you need to do to stop looking dated is to understand what dated really means. Most women feel like there are three categories of in styleness, for lack of a better term. And those are trendy, classic, and dated or out of style. And in our minds, these three categories are siloed, right? Things that are in one can't be in another. And everything fits neatly into one of those three categories. And one of the biggest issues I have with this model is that we tend to define classic, right, that middle one as things I like that my eyes are used to, which doesn't allow for the possibility that things you like go out of style. That is a whole conversation for another time that we actually don't need to have because we already did that one. I have an episode on that called Comfortable is Not a Style. It dives deeper into the whole classic idea. And we will link to that in the show notes. What I want to talk about instead though, is ditching this idea of silos where you're either in or you're out, and instead think about a sliding scale where you can be a little more in or a little more out without fully being one or the other. And on this scale, it can take some time to move up or down, even years. And different items move along that scale faster than others. So instead of those silos, let's imagine that style relevance or instyleness exists on a line or a scale. And over on the right we have trendy, trendy, trendy, trendy. These are the latest, greatest, all the cool girls are wearing them pieces. And they tend to be specific styles or pieces at the very far end of this category. Pieces are often only available from high end designers or fast fashion retailers. You've probably heard me talk about this in my trend episodes, right? That when I can't find those pieces at regular women's stores, it's not time to talk about the trend yet. Then just to the left of trendy, we move into current. And this word causes so much confusion in the style circle. I hope this clears it up. Things that are current make you look like you know what's going on in the style arena at this point on the scale, styles are more widely available from brands and stores where the average woman shops. Current tends to be less about specific pieces and more about the general direction. Styles are going in. And I'm going to give you an example of this in just a minute. But think about the current in a river. It's which way the water is flowing, right? Okay. So you have that in your mind. We're going to give you an example in a second. But then sliding further to the left, we have what I call it just is. These are pieces that don't make you look like you're in the know when it comes to style, but they also don't make you look like you're stuck in a time warp either. This is where most women think they're existing with that whole classic label. And then to the left of it just is is dated. These are the styles or styling that are noticeably out. These are the ones that age you, that make you look like you don't know what's going on when it comes to style. Now let's use jeans as an example for spring. Heading into summer, long, baggy jorts are going to be a trend. I'm just the messenger. Again, that is what will look trendy for spring into summer. Jeans that look current are any number of relaxed, baggier styles. Can you see the difference here? We've gone from a very specific piece that won't be as widely available to a directional concept that can be interpreted in a lot of ways. Barrel legs are current. Wide legs are current. Slouchy jeans are current. Are you with me? All right, then we move down a little bit, and then we have straight legs. Straight legs. They just are. Nobody's going to look at you in your straight legs and go, ooh, girl, she knows what's up. But no one's going to look at you in your straight legs and think, 1997 called, they want their jeans back. They're just. They just are. Then let's take one more step to the left and we get to those high, stretch, skinny jeans that are most definitely looking dated. So that's kind of the trend scale of jeans. I hope that helps. What we're talking about in these two episodes is that left hand side of the scale. The styles and styling that are actually dated not well. They're not as popular as they once were. No, these things are dated. All right. Now that you have a better understanding of what dated really means, the second thing you have to do to stop looking dated is realize that everything, and I mean everything, dates. Maybe not as quickly as something like jorts, but not one single item of clothing is completely trend proof or immune from looking dated. Another thing I like to do when I'm putting my episodes together is to ask my AI again. It's a great way to make sure that I haven't missed something important. And one thing I really didn't want to do in these episodes is make you feel like you have to be chucking your entire wardrobe every two years and starting from scratch. So here's what I asked. How can women keep their wardrobes from becoming dated without replacing their clothes? Often the results were not all that interesting or noteworthy or anything I felt needed to be included. Except for the first strategy, which was invest in quality timeless pieces like a good blazer, well fitting jeans, crisp white shirts, and versatile dresses in neutral colors. Let's talk about that good blazer for a minute. The next thing I did was head over to the Google machine and I searched for Women's Black Blazer 1985. If you are of a certain age, you know exactly what came up, right? The working girl power blazer. And then I changed just one little digit and searched for Women's Black Blazer 1995. The length was longer, the buttons were smaller, and the lapels were narrower. Think Ally McBeal. Then I searched for women's black blazer 2005, 2015 and 2025. And they're all a little different. We're talking shoulder pads versus no shoulder pads, button placement, size and number, pockets versus no pockets, boxy versus lean. Obviously, looking at pictures on the Internet, I couldn't feel the fabric, but I know they all felt very different too. So you can see that even timeless pieces like a great blazer, they're not truly timeless. The best you can hope for is that your items date more slowly, not that they don't date at all. A crisp white shirt, any crisp white shirt is going to hang out in the it just is space a whole lot longer than jorts. But even that white shirt, when compared to one you bought 10 years ago or 20 years ago, is going to look different again. The color, the buttons, the size of the cuff, the number of darts, it just changes. And this is not to say that everything you've had for a hot minute is automatically dated. But you have to allow for the possibility that it isn't timeless just because you want it to be, to avoid looking dated. Another thing you've got to understand is that styles, meaning the actual pieces that you're wearing, date, but so does styling, meaning how you're wearing them. And here's an example. Take the classic short sleeve polo shirt. That's a style, right? Kind of a timeless style the same thing is has been around for ages. Okay, fine. But I remember when we layered multiple timeless polo shirts, right? That is styling, and that styling is most definitely dated. Other examples of styling are things like showing your socks, popping your collar, or rolling your sleeves, tucking, rolling or cuffing your pants, layering a button front shirt under a sweater, stacking or layering accessories, that kind of thing. It's not about the pieces, it's what you're doing with them. And I think styling might even be harder to understand than what specific pieces are looking dated for a couple of reasons. And this is why I wanted to start with styling first. Styling is less concrete than just, here are 10 pieces that are currently trending for the season. Styling kind of feels like an unspoken vibe, right? It's just what we're doing. And it's really hard to quantify or explain a vibe. The other reason is that the places you would normally look for style inspiration and information don't do a great job of actually showing how to wear things. I tell people all the time to go to store websites and look at what's new or to see if the things that you own look like the things being sold. Which is a great way to know if styles are current. But there is often a lack of actual styling inspiration. One of the biggest questions I get in the fall, every fall and winter, is what shoes to wear with different styles of pants. And if you were to go to Nordstrom's website for some ideas, what you would discover is that the only shoes you can wear are heels or strappy sandals. Right? Like, we all know that that's not appropriate or, you know, possible for everyone, but that's what they tend to show them with because that's how the pants look best, right? You're not kind of having to mess with the shoes and, and, and compete with the shoes. It's just easier to show the pants. So stores often either under style the clothes so that the focus is just on the garment, or they over style the clothes in a very editorial way. I'm looking at you, Banana Republic, which looks great, but doesn't help you know how to wear things in real life. Most of us aren't like, let me go horseback riding in a belted cardigan with nothing under it. Like, it's probably not gonna help you much. And one thing I've seen over the years is women adding current or even trendy pieces to their wardrobes, but then styling them in dated ways, which, if you bought the item just because you love it, great. Keep on Keeping on. But if you bought it in part because you want to look current, it's not doing what you think it's doing. You're not getting your money's worth. To look current, you've got to style the current things in current ways. So by now you're probably thinking, woman, just tell us the styling that's dated and get on with it. And I wish I could. I truly wish I could. But how far back do you want to go? I mean, I guess we are no longer using live lizards for accessories like women did in the 1890s, and we are no longer tight rolling our jeans the way we did in the 1980s. So there is so much that I could never, ever, ever give you a complete list. What I can do, though, is tell you a few dated styling techniques that stand out to me right now and then share a few ways you can train yourself to recognize styling that looks current and styling that doesn't. In general, the biggest dated styling issue I see is the tendency to over style, to over match, make things overly perfect and somewhat over the top. Like we used to. Doing these things now makes outfits look overthought and overwrought. It looks visually like you're just trying too hard. When I think about the styling vibe of 10 years ago, it was about showing the perfect amount of ankle between your jeans, your perfectly rolled jeans and your booties. Having the perfect amount of cami peeking out from the bottom of your tee and stacks of big, colorful color coordinated bracelets and lots of pattern mixings of florals and stripes with a matching bold color cardigan over it to really make it pop. Can you guys kind of imagine that? Yeah. The current styling vibe is looking at those things and saying, girl, chill. Just take a deep breath, sit down, be still, breathe. Right now is about understated, relaxed structure, like drapey trousers with an elasticated waist rather than color saturated skinny pants. It's monochrome versus all the colors everywhere all at once. It's a single knot in a silk scarf rather than complicated origami with something that could be used as a blanket or a boat sail. And I really hope that you can start to picture what I'm describing. And here's why this matters. With fewer layers and bold accessories, the pieces matter more. The fit and condition of each piece matters more because that's where the focus is. And I see two things usually happening. First, wearing current items in a dated way, which means over styling, overthinking, feeling like everything needs to just be a little bit more. When really, your current items just need you to relax and let them shine. Choose beautiful pieces and then just let them be. And the other thing is wearing dated items in a current way. And this, my lovely listener, could be a reason why your simple style feels boring, bland, and a little out of fashion. Currently, what we're seeing is more elevated basics, like a good drape on a T shirt or even an extended shoulder. Something to make it look a little bit more interesting. Right? And T shirts are actually the perfect example here. Right now, what's looking the most current in tees is either a fitted, more baby tee style with a shorter, almost cap sleeve, or a relaxed, boxier shape with a longer sleeve than we've been used to seeing in the last few years. That classic fit tee isn't looking super current. Is it dated? No, I don't think so. It's just lower down on that scale that we talked about. But you can see that when all the focus is on that single item. Without a cardigan, infinity scarf, and a skinny belt or the whole thing, that singular piece matters more in terms of how fresh it looks. So if you want to look current in just a tee, you have to have a more current tee, right? Straight leg jeans and a classic fit tee isn't as current looking as a fitted tee and relaxed jeans. The interest in the outfits right now is coming from the pieces rather than the styling. And that's not 100% true that we're not doing any styling. But in general, the interest is coming from the pieces, not from the styling. Now, I'm going to share with you three specific styling techniques or things that I see that are looking dated. And next episode, we'll talk about the pieces themselves. But this week, it's styling also. Again, I am just the messenger. This isn't personal. And again, if you love it, wear it. But if you're doing these things thinking you look current, this may be eye opening for you. So do with the information as you see fit. The first one, this is real specific, but I'm seeing it a lot. Tying your button front shirts at the waist. I am so sorry to my friends who want to define their waist with this little style maneuver, but. But it looks dated. Now, as with everything, there are exceptions to this. I don't think, like a big oversized shirt tied at the waist at the beach looks dated. Right. And a silkier, drapier shirt tied with a bigger knot and longer tails that show just like a little sliver of your midsection doesn't look as dated. But the traditional Toplin denim or chambray shirt tied in a small knot right at the waist looks dated. My sincerest apologies. And now, unfortunately, we have to talk about the half tuck, which is a styling trick I personally love. It lets me define where a waist would be if I had one while still providing some coverage all the way around. Sadly, this is starting to look dated. It's been in, it just is for quite some time, but it's moving down. The current styling is all the way out or all the way tucked in, and I'm finding myself half tucking less and at least giving a chance to all out or all in. There are still some outfits that I think look best half tucked, but I do realize it's not as current and I am trying the other styling to see and, and some outfits. I'm like, man, I could tuck this, or, man, this looks okay out. But it's just an awareness of this isn't the thing anymore. The second thing is wearing long over lean. This is a proportion that we used to love. This is the old tunic over skinny jeans formula. It's important to remember that things change. And we are seeing some slim, er, jeans having a moment, and there have been some longer tops and sweaters out there. But this specific proportion of real long over real lean is not back yet. It still looks dated. And then finally, number three is overdoing it. This is what we've been talking about over layering, over accessorizing, and over tweaking. And what I mean by this, for example, is layering a crew neck sweater over a collared shirt and rolling the sleeves so that your undershirt shows and, and popping the collar and cuffing your jeans and adding a stack of bracelets. That crew neck sweater, it just wants a simple necklace and a couple of bangles, a pair of great pants and a modern shoe. And then it wants to be left alone. So if you find yourself doing all the style tweaks and adding all the layers, you might just need to let it breathe to look a little bit more current. So those are three things that you can be on the lookout for in your own wardrobe and your own styling if you don't want to look dated. But an important style skill, and one you can learn, is to be able to recognize dated versus current styling in the world around you so that you can see when these shifts are happening and keep up with them. If looking current is something you want, the best way to do this, the first thing you gotta do is shock your system. In the beginning of the episode, I told you that becoming dated happens so gradually that sometimes we just don't notice it right until it's like really glaringly dated. But it's hard to tell the difference between styling of two years ago or sometimes even five years ago. But if you look at the styles from 10 years ago, 15 years ago, holy cow, you are going to see it. It's like the difference between one of those daylight alarm clocks that gets brighter so gradually that you don't even notice it. And it's just like a very slow, gentle wake up versus flipping on a light switch in a completely dark room. That one you're going to notice. It's going to be a shock. So what I want you to do is shock your eyes by looking at obviously dated styling again, not two years ago or five years ago. Start with at least 10 years ago and then work your way forward to see the current changes in how we got to where we are now. There are a few ways you can do this. One is to watch movies or TV shows from that time period that have heavily female casts in real life situations. Like, I'm not talking about space movies or superhero stuff. Even shows like the Real Housewives will show you how women have been styling their clothes for 20 years and how that styling has evolved. And maybe you're not dressing like they do in Miami or Beverly Hills, but we're not talking about the pieces, we're talking about just the styling. And if you go back far enough, you are going to notice it. Another way is to go to Pinterest and search for something like spring outfits, 2015 or whatever year you want to start with. This one's a little bit tricky because for years now, Pinterest's algorithm has been terrible and has only been serving updated looks. If you wanted to find something current, best of luck with that. It was all infinity scarves, right? But now, even when I was searching for 2015 or 2020 content, it was only showing me new stuff, which, you know, it's what I want most of the time, but not in this situation. But it's worth a shot. You can try. You can also look at some retail websites and I like the ones that feature some more catalog style photo shoots rather than just individual clothes. Evereve is a very good one for this. Or you can look at stores that feature social media images of people wearing the clothes, not just the reviews. Sometimes they just pull em out of the package and they'll show it even if it looks terrible. But if you look at retailers that show the social media images of People wearing them, they're usually styled. Loft is good for this and so is Target. But the best way I have found to look at dated styling is is to look at relatable fashion bloggers and style influencers who have been at this a long time. Right. They need to have been showing you pictures long enough that you can see the changes. But hopping your way back machine and head to their websites. Our friend Jolynn Shane is an amazing resource for this. She wears clothes in such a fantastic and relatable way for most women and she's been taking great photos forever. We'll link to her site in the show notes, but go back to like 2015 and then work your way forward. You don't have to read every post, but your eyes are going to start to go, oh, yeah, now I see it. I got it. One thing I want to say about doing this is that no matter whose site you're on, there was absolutely nothing wrong with those outfits. They were current and trendy at the time. Sometimes I'll see like a celebrity fashion stylist or someone sharing old photos of herself saying, what was I thinking? Who would ever wear that? Well, what you were thinking was that that was current at the time. You looked great at the time and you did. Even the 80s. OMG, what were we thinking? We were thinking that was the style. It changed. We're no longer doing it. That's all. But if you're still doing your hair like you did in the 80s, that's now dated. And what are you thinking? Right? But we don't judge people's past outfits on current styling standards. But when you're going through these photos, I don't want you to get caught up into pieces. I want you to focus on the styling. How are they wearing the clothes? What are the proportions? What kind of accessories are being worn? How big are the accessories? How many are there? Are they layering? How much color are they using? What kind of patterns are they showing? All that kind of stuff is what we're focusing on in this episode. Once your dated radar is activated and alert, start working your way forward in their blogs and seeing how the styling evolved, how the proportions and the accessories have changed. If the use of color or pattern increased or decreased over the years, these stylish ladies have been putting in the work for a long, long time and they have a photographic timeline of how styling has changed and evolved over the years. They did good work for us. So thank you, ladies. And then finally, I want you to take it to the real world and just look at people. One thing I hear when I meet someone and they find out what I do is they go, oh, I bet you're judging my outfit and I'm truly not. I don't care if you're happy. I'm happy. But I do just look at everyone. It's a great way to get inspiration or see how women are wearing clothes in real life situations and to hone my own style skills. I'm not suggesting that you go tell the woman that you saw, you know, the one who's just minding her own business at Costco, that no one's wearing long over lean anymore. You can just file that away for yourself. But just being able to see it and identify it will help develop that style muscle. And this isn't me just saying words either. What this activity is doing is putting your reticular activating system to work. What the heck is that, you may ask? It's the thing that makes you notice all the white SUVs on the road as soon as you think about buying a white suv. Your ras is a network of neurons above your spinal cord. And one of its jobs is is to connect the subconscious part of your brain to the conscious part of your brain. Your RAS takes something that you're focusing on or that you're interested in. And then when presented with all the stimuli you're taking in all the time, it filters it and gives you what you're looking for. So if you are aware and looking for how people are styling their clothes, your RAS is going to filter through that lens and make you even more aware of it. It's quite literally how that style muscle is built. And the cool thing is everyone can do it. All you're doing is just looking. Your brain will do the rest. How easy is that? If you want to put this episode into practice and make it work for you and not just let it be nice to know information. Here's a little homework for the next two weeks. First, shock your system by looking at dated styling and then work your way into looking at what styling looks current. Now. Then turn on your RAs, go where women are and look at how they're styling their clothes. We're not judging. We're not even just looking for current styling. We're just noticing. It's just information. But if you do this, I bet you're going to feel so much more connected to what's current and so much more confident in your own style. This is the work that matters. Learning is great, it's super important. But doing is the part where you really make changes. In my next episode, I'm going to share 10 specific styles that are dated. They're not trendy, they're not current, they're not even in my it just is category. As Heidi Klum would say, they're out one more time. This isn't personal. I'm just the messenger. Wear what you love, but do it from a place of knowledge. That's what we're all about here. I hope this episode encourages and inspires and even excites you to give your style a bit of an update if it needs one. And if you want one. And just a little word to my Style Circle members, ladies, I can feel. I can feel the is this dated post coming and I have a feeling I won't be able to answer them all. So before you go nuts and post every single item from your closet asking if it's dated, I want you to do the same work I'm telling everyone to do. And first listen to both episodes and do the homework. But I'm going to add a bonus style coaching session just for the Is this dated Questions and I encourage you to attend or watch the replay even if you don't have individual questions because there's so much to be learned from others. So keep an eye out for that date and that time. We will share it with you, but I'm going to take care of you. I'm not going to leave you hanging if you are not a member of the Style Circle yet, but you would love to have a place to ask these questions and get personal feedback. Come join us. The link to join the Style Circle is in the show Notes. It's the fastest way to learn to be stylish for life. All right, that's all the advice I've got for you today. I'll see you next time. And until then, remember that your everyday matters. So get dressed for it and that's a wrap. Thank you for listening today. If you're loving the Everyday Style School podcast, I'd like to invite you to become a member of the Style Circle. It's our monthly all access membership that gives you everything we create to make style easy so you can save time and money, have easier mornings and and more confidence all day long. You get our seasonal capsule wardrobe guides, all of the masterclasses we offer, and our exclusive members only podcast, the Everyday Style School Extra credit. Plus you're invited to the Facebook community where you can get even more style support and inspiration. I would love to get to know you and support your style journey it's just $19 a month less than the cost of a clearance shirt you're never going to wear. Come. Just join me and make your everyday style easier.