How to Tell if Your Clothes are Out of Style

How can you tell if your clothes are outdated? 

It’s one of the most popular question 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 is 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 the subtle details that are aging your piece, hence, why having a second set of eyes is so important.

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 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, and the pants’ style will look like the 90s. 

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

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

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

Was it a Trend?

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

No, it doesn’t. Nothing ever 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. This 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 of the current looks and how they are evolving. 

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 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 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 is 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. 

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, you will date your look faster.  

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Our readership inspires all of our posts and is not sponsored or paid for by brands or retailers. 

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Recommendations are based on my experience as a personal stylist and wardrobe consultant for over a decade. I worked with busy, down-to-earth women who wanted to look chic and feel confident but were often confused by so much of retail. 

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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.

    Reply
    • 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.

      Reply
  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,!

    Reply
  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!!!!

    Reply
  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”.

    Reply
  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!

    Reply

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