How to Tell if Your Clothes are Out of Style

How can you tell if your clothes are outdated? 

It’s the most popular question over in our private Facebook group

Unfortunately there is no one-size-fits-all checklist, or guide to follow. Which is why I tend to shy away from a broad conversation about it. It’s been my experience that when you tell someone their clothes are dated (only, of course, after being asked to) 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 today, I’m going there 😉 

Because you’ll never achieve the chic and sophisticated style you are aiming for if you are hanging onto pieces forever.

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

It’s as simple as that.

How to Tell if Your Clothes are Out of Style

Before we jump into this discussion, a few things to remember:

  • Yes, you might have one or two pieces that you’ve had for a decade or two, and they still look great. These are the exception, and should not be the expectation. 
  • Clothes were not meant to be owned and worn forever. 
  • It doesn’t matter how much money you spent.
  • If your closet if full of old things, your look is dated. 

Simply put, if you think something is dated, it probably is. Listen to your gut.

If, however, your style leans classic, it can be a little trickier. It’s often the simplicity of a classic piece that poses the challenge.

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

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With all that said, let’s get started with 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 simplest most classic piece is going to carry notes of the time it was designed.

For example, say you splurged on a designer classic black suit in the 90s, today it’s dated. The line, the shape of the jacket, the style of the pants will look like the 90s. 

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

Design is based on nuance details, it’s how style evolves over time, so if you’re hanging on to a piece from times past, you’re outfit will reflect that.

Details to consider – shoulder structure, button/zipper/pocket detail, shape of the piece. 

Was it a Trend?

It makes me crazy when someone says, “everything comes back in style.”

No, it doesn’t. Nothing every really “comes back.” Instead, styles of the past influence current trends.

Right now, for example, trends are primarily influenced by the ’90s. I hit my prime in the late ’90s. I wore everything from slip dresses, cropped tees, and flare jeans. And they are all back, but I could not wear what I wore in college today without looking nuts. 

To that point, more recent trends have a shelf life. Which is why, if you care about this stuff, casually following what is going on in fashion is helpful. Pinterest is an incredible resource for getting a visual on what the current looks are, and how they are evolving. 

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Vintage and Second Hand Finds

Before we get into this part, it’s important 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 higher quality from 1980 or older. Most pieces are desirable from a collector’s perspective or fit a certain aesthetic. I’m a big fan of vintage when done well, but remember it often requires extensive alterations to make the clothes of the past work for modern times.

Vintage can be found in both consignment and thrift stores, although with its explosion of popularity over the last decade, it’s become its own retail space. 

Next, we have consignment stores – a “higher-end” version typically with better, more modern, and current brands. Gently used merchandise is bought between the store and an individual. 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 it’s not edited (or edited well) when it hits the floor.

This is where we get ourselves in trouble because there is simply too much stuff and the majority of it we don’t need. 

This is 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 tons of discipline.

You have to understand that you get less life out of these purchases because they are coming into your wardrobe already used. If your closet is full of second-hand finds that you’ve hung onto for a while, your look will get dated faster. 

Keep or Toss Party

Because this is so specific I am going to host a “Keep or Toss” party over in our Private Facebook group. All you have to do is be a member (and thousands of your already are).

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If you’re not part of the group, you can join here. PLEASE answer all of the membership questions so I can approve your request.

Once you join, wait for me to post the details, today, at 11am EST. 

You’ll be able to post a picture of one piece from your closet that you’re wondering about and I’ll simple say “keep” or “toss.”

Again, please wait for more instructions to be posted in the group. I’ll have to delete any post that is outside the scope.

This is designed to not only help you individually but create a visual of real-life pieces that will allow you to start to see the subtle nuances of how and why a piece begins to go out of style. 






How to Tell if Your Clothes are Out of Style

13 thoughts on “How to Tell if Your Clothes are Out of Style”

  1. 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.

    • 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.

  2. 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,!

  3. 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!!!!

  4. 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”.

  5. 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!


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