Am I Too Old To Wear That Trend? 3 Questions To Ask

My teenage daughter is obsessed with thrifting, and her latest shopping scores have given me major flashbacks.

“It’s so Y2K!” she said while showing off her freshly picked black velour hoodie with the gold JUICY LOVE YOUR COUTURE splashed across the back.

vintage juicy hoodie fountainof30

It reminded me of what I had from that era.

So I dug up an old pair of dark wash 7 for All Mankind, low-rise flares for an IG reel that focused on different denim styles.

My daughter saw me and asked, “You have low-rise flare pants?” This is another style that has recently started to fill her drawers.

“I do!” I said.

This particular pair was a score from Saks Off Fifth, way before the discount store came to the city. So it felt like such a steal at the time.

Then she asked, “Are you going to wear them?”

That’s the million dollar question! When you participated in the trend the first time around, and now see the young ones taking it and making it theirs… do you really want to be a part of it a second time? 

Or will it just make you look older and like you’re trying too hard to be young and trendy?

As a personal stylist, I get this question ALL the time.

My clients constantly ask if something is appropriate to wear. Whether it’s a mini skirt, slip dress or low-rise jeans, they see these styles on celebs and social media and wonder if they can pull it off too.

If you’re wondering the same thing, keep reading! 

I’m sharing how to tell if you’re too old for that trend.

3 Questions To Ask Yourself When Deciding If You Should Still Wear That Trend

1. Why do you want to wear it?

When deciding what to wear, intentionality is key. This means you must be clear on WHY you’re wearing it. I always advise my clients to think about HOW they want to feel during the day and then dress to express that feeling. 

So if you’ve got a pair of low-rise jeans still hanging in your closet, like I do, ask yourself why you want to wear them.

Is it because they make you feel young? Sexy? In-style and relevant? Then back your answer with the truth. Is that really how you want to feel in the circumstances of your day? 

If you’re going on date night, then maybe you do want to feel young and sexy. Great! Move on to the second question.

Or maybe you’re meeting up with friends and you want to feel in-style and relevant. OK. That’s valid. The goal here is to be super clear about WHY you want to wear the trend. Once you know this, move on to the next question.

2. Do you feel confident and comfortable?

No trend should ever disrupt your confidence and comfort level. That’s why you must try on the garment and be really honest with yourself. There’s the basic comfort level fit-tests that determine if you can move freely in the garment. But also gauge whether you still feel like yourself. Does the trend take you into another persona? Playing dress up and having fun with fashion can provide liberties to express different aspects of your personality. But you never want to feel like you’re pretending to be somebody that you’re not. 

If you still feel confident and comfortable in the low-rise jeans, then you’re ready to move on to the final question.

3. Do you look good?

Now it’s time to take a full length mirror selfie wearing the trendy item. I always recommend taking a photo instead of making decisions based on the reflection because it allows you to see yourself with more objectivity.

 Then decide if you like how you look.

Sometimes women ask their partner or a friend for their opinion in this situation. I don’t recommend this. Always get dressed for how you want to feel and not what others think.

So how do you feel when you see your photo?

Do you feel sexy, confident and comfortable? If yes, then wear the low-rise jeans!

Are you questioning something about how you look? 

Be aware when this happens. Your questioning shows up in a sneaky way that may try to trick you into wearing something even though you’re not fully confident or comfortable.

Look out for thoughts like this:

“I love the jeans, but maybe I’ll wear a longer shirt to cover up a bit.” 

You can detect this sneakiness by noticing when you add the word “but” into the sentence.

“I like them, but…”

“They’re so cute, but…”

This “but” is revealing your insecurities. You’re not feeling confident or comfortable. In this situation, do not wear the jeans.

If you are happy with how you look and there’s no sneaky thought trying to get you to hide, then wear them!

It’s all about feeling confident and comfortable because when you do, you can wear anything you want.

As for my 7 for All Mankinds, I wore them to run errands to see how I felt. (Side note, this is a great, low-stakes way to try out the trend after you’ve gone through the 3 questions.)

not too old for trends elysha lenkin fountainof30

They passed the test! 

Granted, they weren’t as low-rise as the Daryl Ks I wore in Y2k. You know, the ones with no back pockets that show butt cleavage without even bending down…

Now I want to hear from you. What trend were you considering wearing and did you end up wearing it or not?

Tell me in the comments below

– Elysha Lenkin 

Elysha Lenkin is a personal fashion stylist who helps women look current, feel confident and stay true to themselves. For over 20 years she’s styled hundreds of women in all shapes, ages and sizes including Carrie Underwood, Tina Fey and Serena Williams. Get her free style guide to help you shop your closet and put together a new outfit using your old clothes here. See Elysha’s denim styles IG reel here.

You may also like to read more of Elysha’s styling posts like Expert Tips: How To Score Big Shopping Vintage Fashion and 3 Style Hacks To Get You Through The Holidays.

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