Jennifer Mackey-Mary: Are you ready to find out if what you’re wearing is out of style? If you’ve been following along, you know this is part 2 of our Stop Looking Dated series, and today, I’m sharing 10 specific pieces that have had their moment, but now are killing your quest to look current. Let’s get started

Hello gorgeous, 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 the founder of Everyday Style, where we’re on a mission to inspire women to love the way they look and give you the tools to make getting dressed easy.

This is the second half of our Stop Looking Dated series. Part 1 was all about styling, or HOW we’re wearing our clothes. If you havent’ listened to it yet, go check it out and then come back to this one. The description of my scale of trendiness will help you in this episode. If you don’t go listen to it first, go back and listen after. Either way, looking dated is about wearing dated things–that’s this episode in a dated way–that was the first one, and you’ve got to understand bot, so be sure to listen to both episodes

I’m not going to ramble on today, I know you just want me to tell you what’s dated, and we’re going to get there, but I have a couple of disclaimers before we get to that.

First and foremost, and I bet you know what I’m going to say, But with the world, and the internet being what it is, I need to say again, wear what you love. If in this episode, I describe your 10 favorite items, and you love them, great–keep wearing them. I don’t want to see any of our members saying “Jen said we can’t wear that any more”. No I absolutely did not. What I am saying is that you can’t keep wearing them and thinking they look current, or that they’re helping you look current. 

In my last episode, I talked about how women use the word classic to mean “styles my eyes are used to”. I also see a lot of women using “current” as a catch all to mean “things I bought that I still enjoy wearing”, rather than understanding that the force of your love no matter how strong, will not keep items from becoming dated. Doesn’t mean you can’t love it, doesn’t mean you can’t wear it, but it also doesn’t mean it’s still in style.

The second thing I want to mention is that this information is accurate as of April 2025. If you’re listening years from now, hello future lady, I hope its nice where you are. Please don’t take this advice before verifying if it still applies. As we talked about in part 1, things are always changing, moving up and down that trend scale. 

Third, this is not an exhaustive list. There’s no way I could list all the things that are out of style Guess what everybody, poodle skirts are no longer in style.These are 10 things that are recent enough that you might not know they’ve become dated, but even then, I know there are more. 

If you are a Style Circle member, we have added a special Style Coaching session where you can send in photos of your items or your outfits and I’ll tell you if they’re dated or not, or how to tweak your look to make it more current. So while I can’t list all the things that are current or dated, I can answer as many of your questions as possible. That’s happening Tuesday, April 29 at 7:00pm central If you’re not a member yet, there’s time to join before the session, and if you’ve missed it, the replays are always posted to watch on your own schedule.

Finally, this is not personal. It isn’t meant to offend you. I know I am about to describe things that some people are wearing while they’re listening, and I know the immediate reaction can be to feel a little hurt. After all, it can feel like I’m critizing, and I’m absolutely not. I’m just the messenger.This is just information about 10 pieces that are no longer in style. What you choose to do with that information is up to you. I want you to make style decisions from an educated perspective. Thats all. I still think you’re wonderful.

Ok, with no more disclaimers or preamble, here are 10 items that have seen more stylish days. 

#1 Let’s just come out of the gate swinging with #1, and this one will probably ruffle some feathers, and that is a classic denim jacket. In a bonus trend episode in the podcast for our members, I shared about a year and a half ago that these had moved out of looking current, and were sliding down the trend scale, and since then, they kept sliding, and now they look dated. 

I’m talking about the denim jacket that’s somewhat fitted, hits below the waist, or at high hip, has lots of seams through the body. You know the one. We wore them over our swing dresses with a long necklace and round toe ballet flats for years. I know you know. 

Denim jackets are everywhere right now, and can look super current…but not that one. That one looks like it came from a bygone style era. 

I know that someone out there right now is thinking, that can’t be true, they’re still available to buy, and yes, they are. You can absolutely buy brand new things that are dated, and you might be confused by that because you’ve probably heard me tell you that to know if something is current or not, go to a stores website, and look at what they’re currently selling. Does your thing look like theirs? If not, its probably dated.

I stand by that, it’s a very easy way to get some quick insight, but there are a couple of things you need to watch out for. 
The first is, which stores are you looking at? Take department stores like Macys, and retailers like DSW out of the mix–they sell too wide a variety for your search to be helpful. Instead, go to smaller brands, and here’s the important thing. It has to be a store that in general, has a more with it aesthetic. No hate to coldwater creek, they have some great basics, but when we start looking for the trends we want to incorporate in the capsule, we don’t check to see what coldwater creek has. If you like coldwater creek clothes, fabulous but to know if they’re current or not, you’re going to have to do a little more detective work.

One of the fastest ways for me to see where an item is currently falling on the trend scale is to see WHERE it’s being sold. If you google something at it only comes up on ebay and amazon, and some stores you wouldn’t consider to be stylish, chances are it’s dated. 

But where it’s being sold is only part of it. The other part is, how prevalent is it. Take boot cut jeans for example. There was a time where boot cuts were THE THING. Then skinnies came along and dominated, and bootcuts looked dated, but they never went away completely. You could buy bootcuts at every denim retailer, but instead of having 10 styles and washes, they had one. 

Getting back to the classic denim jacket. I looked at Gap, which I would consider to be a retailer that sells current looking clothes, and has always been known for their denim. They are still selling their classic icon denim jacket, so on first glance you’d go, oh, still available, I’m good. But here’s the thing. When I filtered for women’s denim jackets there were 29 results. Out of those, 1 was the classic icon denim jacket. That’s only 3.4% of gaps denim jacket offerings. The others were cropped, or longline, or had a peplum or a barrel sleeve, or were a utility jacket style or a bomber jacket style. They all had something that updated the classic denim jacket into a current looking piece. So even if retailer you trust is selling something, look at how many they’re selling. If it’s just one or two, you have your answer. Rest in peace, classic denim jacket, I know we’ll see you again someday. 

Number 2) is big earrings. I’m talking the big old teardrop earrings, especially the leather ones, chandelier earrings and overly done metal earrings with filagree detailing or other texture. And honestly, that appliles to most jewelry right now. These are styles that worked with earthier, boho styles of days gone by. If you look at what’s current, it’s smooth metal, or has inlaid pearls or crystals–its just a lot more refined looking. The two exceptions to the big earring thing is hoops..bigger hoops are still current, but keep them on the understated side. Also, long, linear earrings are current, so if you want to make a statement, add those to your accessory collection.

Dated item #3 is low shaft and overly stylized booties. Let’s start with the shaft height. Anything that’s at the ankle or below, is dated. Booties that are more current have a higher shaft-more in the 6” range rather than the 4. Remember, we’re not trying to show a sliver of skin between the jeans and the boots anymore.  Also, like everything else we’ve been talking about, less is more. Booties with v cutouts on the sides are dated. Perforated booties are dated. Strappy ankle boots are dated. Peep toe and laser cut out booties are dated. If you want a boot that looks current, choose one in leather or suede with a higher shaft and an updated heel–avoid the stacked cone shaped heel–and let the simplicity do the talking. 

#4 back to accessories with long necklaces. Look, I used to be a huge fan of long necklaces. I had quite the collection, but for the last few years, they haven’t looked super current, and some of them are solidly dated. Long, simple pendants aren’t as dated but it’s time to let go of any boho feather, and i am seeing some longer cord necklaces coming back on the scene, but what I’m talking about is the long, beaded station necklaces that look like they would have been sold at a home party in 2012. Like, you can wear this 12 different ways, you can wear it long, or wrap it around your neck or wear it as a belt. If you’re having trouble visualising this one, here’s what I want you to do. Head to ebay and search for long necklace, and then insert any direct sales jewelry company-stella and dot, premier designs, silpada, park lane–I know there are some I’m forgetting. Or, search for jjill long beaded necklace. You’re going to know exactly what I’m talking about real quick. 

Number 5 is mid-thigh cardigans. Ill be honest, I don’t think this one is as dated as some of the others on this list.. Another dated sweater style is super chunky sweaters–like oversized cable knits or really wide ribbing around the neckline and down the front,  and I think the time warp magic really happens when you put them together, but there are some very beautiful, high end, high quality minimalist longline cardigans that could be styled into my “it just is” category for an office setting, but it would take everything else in your outfit looking updated, and I’m definitely not talking about the open, longline cardigan you bought at loft or lands end years ago. If you want to look more current without so much effort, go for cardigans that end hip length or higher, and throw in some buttons.

All-right We’re halfway through–hopefully I haven’t ruffled all of your feathers–but there’s still time! 

Let’s move on to dated item #6 which is slip on sneakers.I’m not talking Kiziks, or running shoes you don’t have to tie and untie, I’m talking about more of the vans style. These were super cute with skinny jeans rolled up, but with full length pants, or wider leg crops, they just look dated. And you’re going to lose extra current points if you’re still rocking those higher vamp or mid top styles with zippers–especially two zippers on the sides of the vamp. What’s current right now is lace up sneakers with a thinner sole than we’ve been seeing in the last few years, or if you want an easy slip on shoe, go with a boat shoe or driving moccasin 

At number seven we have a pattern, and maybe this isn’t a specific item, but you can just apply it to any item of clothing with bold, high contrast, geometric prints. I’m looking at you, chevron. One thing I was struck by doing my research for dated looks was all the high contrast prints. Bright aqua with bright white, black with bright white. It was jarring because I realized, we’re not seeing that any more. I hit up ebay to search fo geometric print blouses–which is a good search if you want to get a visual of what dated blouses look like–and I had overwhelming deja vu as I looked at so many blouses, mostly stitch fix ones–that I had seen in client’s wardrobes during their closet edits. And they’re memorable because I probably saw the same blouse 50 times. It leaves an impression. My point though, is that I haven’t done a closet edit in over 6 years, and I specifically remember telling people it might be time to part with that blouse at the end of my in-person styling career. So almost 7 years ago I was telling people it wasn’t looking so fresh. Patterns now are lower contrast, more organic and randomly placed, smaller scale and more subtle–or any combination of those. I’d also like to give a special dated shoutout to old school boho prints as well. While you’re on ebay looking for geometric blouses, do a quick search for boho print top. You’ll see what I mean. This is that overstyled, overworked look I was talking about in the last episode. 

Let’s stay on that theme for #8 and that is ballet flats with overstyled toes. I’m not talking about the tiny little bow that’ve been around since ballet flats were invented. I’m talking about details on the toes like folds of leather, ruching, superfluous straps, big ol round or oval buckles.I’m going to be honest, these have always been tough to pull off, because when these styling details were big, the toe was also very round, which cuts off the leg line, and can look kind of frumpy, and then you highlight your cut off feet with an attention getting detail. Going back to my one on one days–again, the mid 20-teens, I was on a quest to get these out of my client’s closets–especially in a professional setting. There was an outfit I used to call the Junior Associate Uniform, and it was a printed shell top, an open cardigan, trouser pants, and these flats. Even in 2016 it screamed, please don’t pay me what I’m worth. Before we move on to #9, here’s a great example of what i was talking about in last week’s episode regarding my thoughts on classic, and how EVERYTHING dates. In my ebay ballet flat search, there was a pair of short round toe, black patent leather with a huge oval silver buckle on the toe. The title of the listing? Classic Black Ballet Flats. Not so much. Ballet flats in general are classic, these flats specifically are not. It’s like jeans, blazers, white shirts. Even they evolve. The ballet flats of now times are you guessed it–a little more refined, squarer and pointer toes are modern looking. If you want something that makes a little more of a statement, try a mesh or woven style, or even a mary jane

Ok, dated item #9 is distressed jeans. And really, overly distressed jeans are what we’re talking about today, but I think any distressing other than a simple slash on the knee isn’t looking super current. If we can see the stringy holes, nah. If those stringy holes are on your thigh? Double nah. And if you’re saying, but stores are still selling them, come on, you know I come with receipts. On Jcrew, out of 68 jean listings, 2 had any distressing at all, and none were anywhere but the knee. On madewell, also a great source for current looking denim, out of 110 listings, there were 3 distressed ones. Loft had 153 listings with just one lonely distressed style. Remember, it’s not just IF its out there, it’s where it is, and how much of it there is.Those matter just as much. 

This is also a good example of why you can’t put style advice in your head and keep it as gospel for ever. Years ago, I was encouraging women of a certain age to embrace distressed jeans–they didn’t have to look like they’d been mauled by a bear, but it was an easy way to look  current. Now that the current has changed and is flowing in a more refined and polished direction, that’s no longer true. It was true at the time, it no longer is, that’s how style works, so don’t get too attached to any wear this, not that advice. The only thing that will serve you forever is the principles and skills of creating your own style and dressing yourself for life. Those things last, so put your efforts there, and when style change, which they inevitably will, you’ll know how to dress yourself in whatever current you find yourself in.

#10 on the dated list–last one–is oversized scarves. Friends, I can’t tell you how many times I recommended a youtube video from Wendy’s lookbook on 25 ways to tie a scarf in 4.5 minutes. The big scarf and all the ways to wear it was all the rage, and part of that overstyled look that seems to be a running theme. The video is still there, you can look it up if you want. The video was great, wendy is fantastic, but in 2025, if you want to look current, there are not 25 ways to tie a scarf. I don’t know exactly how many there are, but it’s way, way, way less. First, heavier, bulkier, bigger scarves that you can manipulate like that look dated no matter how you’re tying them–whether in a triple knot bird of paradise style, or just looped around your neck. Silkier square scarves are what’s current now. If you like a bigger accessory look, Tie it bandana style and tuck it inside the collar of a tucked in button front shirt. You can also fold it into a skinnier rectangle and tie it in the front or side, flight attendant style, this works inside collared shirts, or over a crew neck sweater. You can use square scarves in your hair, and tie smaller ones on your handbag handles. You can still get the boost of color or pattern you’re looking for with a scarf without having one fully consuming your upper body. 

As as with everything I’ve talked about today, there’s an updated version that will allow you to keep wearing the pieces you love, and look current at the same time.

Ok, there you have it - 10 items that are dating your look, whether you know they are, or not. Remember, now you have the knowledge and can keep wearing them or not. One more time, in case anyone missed it the first 17 times, wear what you love. This advice is for women who want their wardrobes to look current or at least not noticeably dated. If you don’t prioritize that, keep on keeping on. I’m just the messenger, don’t come for me. 

I hope your biggest takeaways from these two episodes are first, a better understanding of trendy vs current, vs dated, and the reminder that every piece you own will eventually become dated, it’s just a matter of how long it takes. The other thing I hope you’re taking with you is the general shift in styl-ING and styles away from overeverything–over accessories, over styled, over done, to a more polished, relaxed look. Getting this current styling right involves investing a little more care and thought into each piece, because we just aren’t using all of the smoke and mirrors for distraction anymore. 

Style Circle members don’t forget the special coaching session we’ve added on April 29th at 7pm central. Attend live or submit your questions in advance, and then watch the replay. Whatever works best for you.

That’s all I’ve got for you today. I hope you found these episodes beneficial, and that you’re not too mad at me. I’ll see you next time–and until then, remember that your everyday matters, so get dressed for it!

Jennifer Mackey-Mary [outro]: 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 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 gonna wear. Come join me and make your everyday style easier.