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How to Tell if Your Clothes are Out of Style

How to Tell if Your Clothes are Out of Style

We are in the middle of our Spring Wardrobe Challenge over in our Facebook group. 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. As they begin to compare the styles they like to the styles they have, 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, of course, 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 today, I’m going there 😉 

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 on you. These are the exception and should not be the expectation. 
  • I am not saying you shouldn’t hang on to certain things. Special pieces are special for a reason. I have some garments in storage for my girls when they are older, most are designer pieces like a Burberry Trench and a pretty fantastic collection of DVF wrap dresses. They’ll be able, if they want, to wear them, but they’ll style them modern pieces in their own closets. 
  • 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. Ask your daughter or best friend, someone who isn’t worried about your feelings (lol) for their totally honest 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 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 era. 

Dated is More than Style

Clothes wear out. 

Fabrics fade, seams weaken, the piece generally looks tired. So if you are hanging on to something that was loved and served you well, but is starting to physically show its age, it’s time to say goodbye and replace it with an updated version. 

It’s in the wear and tear that a garment will also start to look dated. 

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 14 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. I wore everything from biased 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, like, YOUR 90s. It’s better.”

Just proving that if a trend “comes back” it’s not really meant for the original wearer. 

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. 

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

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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.


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:)

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