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How to Tell if Your Clothes are Out of Style

If you feel like it’s hard to figure out if some of your clothes are out of style, it’s because it is!

Over in our Private Facebook group, we are in the middle of our Spring Wardrobe Challenge.

At this point in the challenge, participants are stepping into their closets, armed with style inspiration pictures and a breakdown of how they spend their time.

Then, as they compare the styles they like to the clothes in their closet, we get some big takeaways and lots of questions. 

The biggest question tends to be: how can I tell if my clothes are out of style?

Unfortunately, there is no one-size-fits-all checklist or guide to follow. 

So I tend to shy away from a broad conversation about it because it’s been my experience when you tell someone their clothes are dated (only after being asked), you can still hurt their feelings. 

It’s not welcomed feedback.

In the past, when I have offered solicited advice, it turns into a debate that I don’t want to engage in. 

But here’s the deal:

You’ll never achieve the chic and sophisticated style you desire if you’re closet if full of dated clothes. 

If 1 + 1 = 2, then dated clothes do not equal modern, current style.

It’s as simple as that.

Before we jump into this discussion let me say this:

Yes, you might have one or two pieces that you’ve had for a decade or two, and they still look great on you. 

These are the exception and should not be the expectation. 

If you think something is dated, it probably is.

How to Tell if Your Clothes are Out of Style

Trends and Styles Come In and Out. 

2010 was a whopping 12 years ago, and the oversized bauble necklace had a chokehold on many of us. 

But styles evolved, and now the modern look is understated and layered. 

You can start to see trends come in and out of style. For the longest time, these necklaces were everywhere until they weren’t.

It’s the same for our clothes.

The challenge, however, with classic clothes is that the more simple the piece the harder it is to see when it becomes dated.

We often think that “classic” means forever, but it doesn’t. 

And this is perhaps the biggest issue; the longer you look at something, the less likely you’ll be able to notice the subtle details that are aging your piece, hence, why having a second set of eyes is so important. 

Ask your daughter or best friend, who isn’t worried about your feelings (lol), for their candid perspective. 

With all that said, there are a few guidelines to consider:

When Was it Purchased?

The easiest way to figure out if something is dated is to consider when you purchased it.

Clothes are not made or designed to “last forever.” Even the most classic piece will carry notes of the time it was designed.

A dress you bought in the early 2000s will look like the early 2000s.

Pants purchased in 2010 are 12 years old now. 

Design is in detail; it’s how style evolves. So if you’re hanging on to a piece from times past, your outfit will reflect that era, not the new classic.

This is why keeping an updated Pinterest Board is so helpful, because the more you observe styles the easier it is to see them evolving. 

Dated is More than Style

Clothes and shoes wear out. 

Fabrics fade, seams weaken, and the piece generally looks tired.

So if you are hanging on to something that you loved and served you well but is starting to show its age, it’s time to say goodbye and replace it with an updated version. 

Wear and tear in a garment makes it look dated too. 

Understanding Trends

“Everything comes back in style.”

No, it doesn’t. 

Nothing really “comes back.” Instead, styles of the past influence current trends. 

The other day, my almost 15-year-old daughter started to explain how, right now, trends are influenced by ’90s style. 

No kidding, I thought. 

Many of us hit our prime in the late ’90s or early 2000s. 

Then, I wore everything from bias-cut slip dresses, cropped tees, and low-rise flare jeans. 

And they are all back, but I could not wear nor would I want to wear what I wore in college today.

I would look nuts. 

When I told her I could help her put some outfits together, she chuckled and said, “Oh, no, it’s not your 90s. It’s better.”

And she’s right.

I use to hear clients tell me they were holding on to something for when it comes back. And my challenge to that was always, “you are not going to be the same person when it comes back around.” 

This new 90s trend is a great example of that. I was 19 in 1998. Now I’m 42. 

Why would I want to recreate the looks I wore back then? 

How You Style Things Matter 

There is a lot of conversation about skinny jeans these days.

Are skinny jeans out of style? Can I still wear them? 

I believe you can absolutely still wear them, but to keep your look modern, change up how you style them. 

Instead of pairing them with a  long cardigan swap it out for a boyfriend blazer. 

Or, add a straight leg jean into your rotation so you have some variety in your wardrobe. 

A Note on Vintage and Second Hand Finds

Before we get into this part, it’s essential to understand the difference between vintage and second-hand finds and how they work in your wardrobe. 

Think of second-hand shopping as the general category, with various subdivisions, including vintage, consignment, and thrift. 

Generally speaking, vintage is anything of designer/higher quality from 1990/1980 or older. 

Vintage can be found in consignment and thrift stores, although that’s becoming more rare since it became popular over the last two decades. Now you have to go to stores that specialize in vintage. 

Next, we have consignment stores, who source their merchandise from individuals and only purchase items that meet their quality standard.

For example, I walk in with a popular label dress that’s newish, in excellent condition that I originally paid $250 for; the store takes it and sells it for $100, and when the sale is complete, I get $20 for it.

Then there is thrift, where the clothing is donated, and the resell cost is low—the merchandise is not edited (or edited well) when it hits the floor.

It’s been my experience that thrifting is where you can get in trouble because there is too much stuff, and most of it you don’t need. It’s similar to shopping sales, buyers are romanced by the price, not the need. 

Not to say that you can’t shop thrift.

The resell retail landscape is changing every day.

Maybe you do it for budget reasons or to manage your eco-footprint. To thrift shop effectively, you have to know the brands, labels, and styles that work for you and practice discipline.

You have to understand that you get less life out of these purchases because they come into your wardrobe already used. 

If your closet is full of second-hand finds that you’ve hung onto for a while, you will date your look faster.  

How to Tell if Your Clothes are Out of Style

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Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Sunday 25th of December 2022

Be careful buying on discount or sale price because companies are selling retired style cloths or cloths that don't sell they know you will buy because of the name brand mean while u buying a out of date cloths


Wednesday 13th of April 2022

This is a great post! And so helpful.


Wednesday 13th of April 2022

I'm struggling with making the switch from my skinny jeans (I think they look better on me), I am actually trying different brands just to find the right straight fit for my body. What I really need to know: are leggings in or out? lol


Tuesday 19th of April 2022

@mary, you took the words right out of my mouth. 😂

Tracy Gray

Wednesday 13th of April 2022

Oh my gosh!!! I feel like you were hearing my conversation with my daughters we just had recently. I was going thru my closet and they were offering suggestions on what to keep and what to get rid of. This post was so me! I love to follow your suggestions and make purchases and I love them. But I also can’t for some reason get rid of some of my older things-even though I haven’t worn it in some time. I keep telling myself maybe I will wear it someday and I can’t part with it. My daughters had different ideas and actually despite some back and forth discussions, I did grid my closet of my older clothes and am staring fresh. So when I read your post I laughed because I am so guilty of holding on. Thank you!!!!


Wednesday 13th of April 2022

This is a great argument for a small, carefully chosen wardrobe of good-quality garments that you pay a bit more for - quality over quantity - wear the daylights out of, then replace as needed. You will have gotten your money's worth from them, have looked good in the process, then be able to replace with up-to-date styles.


Wednesday 13th of April 2022

First, let me compliment you on your choice of cover photo for this post - Joan Cusack is a national treasure, and Working Girl is a classic. Thanks for that this morning!

I recently lost a significant amount of weight, and found your site in my search to be thoughtful about replenishing my wardrobe for my new (old) body. Thinking about style in this way is new for me. I've always thought about cut and color, but not necessarily if something is on trend, or reflecting a former trend in an updated way. Thanks for giving me another way to look at things! I'm behind on the spring wardrobe challenge, but I'll be catching up with this new food for thought!

Megan Kristel

Wednesday 13th of April 2022

It's one of my all time favorite movies. :) Trends are important because some of them become classics. So I wouldn't live by them, but they are an important part of how modern style evolves.


Friday 9th of April 2021

I agree with your post completely, but I really wish I had held on to some of my straight skirts from my corporate days in the 1990s. We called them “straight” skirts, then, not pencil skirts, and, personally, I feel they were much more flattering than pencil skirts that nip in at the lower leg, emphasizing the size of one’s hips, and making it difficult to walk in. I’m sure I’m dating myself, but I think ease of movement adds elegance to a look, and I definitely disagree with a bare-legged look in the office. Some things change not for the better.


Wednesday 13th of April 2022

@Judy, I agree with you on the bare-legged look especially for those of us who are a bit older. It's now nicer weather when I could wear dresses but these almost 60-yr-old very white legs are not attractive and it's still not that warm. I have some very sheer hose that I wear from time to time but I'm wondering if I just have to wear pants at this point. Thankfully, I'm only in the office two days a week.


Tuesday 16th of March 2021

I use an app called Stylebook. I photograph every item of clothing that I have, and make a note of what it cost, where and when I bought it. You can keep track of all of your clothes, and put them together in outfits. You can then attach that outfit to the calendar, so you can keep track of when you wore it. Also, best of all, you can look at the stats to see which items in your closet are the most and least worn. It really gives you a good insight into what your favorite items are, and vice versa.


Thursday 16th of April 2020

Great blog. I actually know a person who dated each piece of clothing, purse , shoe box with date and cost. Very nostalgic as I am going through . But I need this for myself!


Thursday 16th of April 2020

Looking forward to joining! Thank you!


Thursday 16th of April 2020

This is the best! I can't wait!! :) Thank you and have a great week:)

Donna P

Wednesday 15th of April 2020

Thank you. Love this post!


Wednesday 15th of April 2020

Thank you, you’re the BEST!!!!💕💕💕


Wednesday 15th of April 2020

Hi I am not on Facebook either but love this idea! I don’t have any pieces that are old but since I like a classic style I worry that I look frumpy and want to try to avoid that or avoid looking like an “old lady”.


Friday 5th of August 2022

@DJ, I also have clothes that are 10 yrs. or older. Some I've only worn once or twice and feel guilty about getting rid of them, but, now I'm realizing I probably never wear them. I think it's to do with the money I've spent and that I really like what I purchased yrs. ago. But , what good are the items if their just taking up space in my extra closet?


Tuesday 16th of March 2021

I agree! I don’t have decades old clothes but what about pieces from the past 10 years? I have a classic style also. Thanks. DJ


Wednesday 15th of April 2020

Looking forward to seeing this idea unfold on FB. 😀 Lesley from Dallas


Wednesday 15th of April 2020

Thank you so much for doing this! Would you prefer to see a picture with us wearing the item or on the hanger? Can’t wait!!!!

Megan Kristel

Wednesday 15th of April 2020

Whatever you're comfortable with - on you is best, but I can figure it out. :)


Wednesday 15th of April 2020

The best idea I’ve heard in ages! I wish there was a way to tag our clothes with the date we bought them! That would be helpful/ funny/ embarrassing! He, he,!

Matthews Deborah Jordan

Wednesday 15th of April 2020

Love Amanda’s comment! Please do this!


Wednesday 15th of April 2020

I love that you're doing this! Determining when something is dated/what makes it dated (especially in clothes from the last 10 years) is difficult for me beyond obvious trends.

Would you consider posting a few common themes from the posted pictures (or a lookalike style) to either your blog or Instagram story? I would love to learn more about items people are unsure about and to learn what's influencing your response of dated or not, but no longer have a Facebook to join the group.

Megan Kristel

Wednesday 15th of April 2020

Hey Amanda, I'm doing it on Facebook to keep the conversation private. I totally get how it would be helpful to share it here. Unfortunately, if I put their pictures here on the blog I can't control what happens to them and I don't want them on the internet, it would invade their privacy.