Are You Too Old To Wear That?

too old to wear that

Style Confidence: Elysha Lenkin

True Religion and Juicy Couture — so Y2K!” exclaimed my teenage daughter while holding a pair of jeans and a velour hoodie.

Major Moment In Fashion:

We were thrift shopping in downtown Manhattan, and although we were in our neighborhood, those brands brought me back to the early 2000s.

“These were the kind of pants that included your underwear with the waistband.”

I thought about what I wore and remembered a pair of low rise jeans. These were the kind of pants that included your underwear with the waistband. They were that low! And speaking of lingerie as part of an outfit, I loved my slip dresses back then! Both styles — low rise jeans and slip dresses — are having a major moment in fashion right now. But can I wear them…again?

That’s the answer many midlife women want to know! If Gen Z has taken a trend that you used to wear, and made it theirs… Can you jump on board? Even if it’s the second time? Or will it age you? Or make you look like you’re trying too hard?

Is This Appropriate To Wear?

My personal styling clients ask this often:

Is this appropriate to wear?”

They may be referring to a micro mini skirt or a super sheer dress (both big at the moment!) Because they see these looks on their social feeds, and want to know if they can wear them too.

If you’re curious about the same thing, this post is for you! I’m sharing how to decide if you should wear that trend.

“Do you still love them? Or do you think they’ll make you look cool? Be truthful!”

Why Do You Want To Wear It?

Intentionality is everything in personal style.That’s why you must know WHY you want to wear it. Is it because you want to feel young and hip? Like you’re with it and in the know? Or is it because you genuinely love the style?

“Are those flared?” my daughter asked me while pointing to my pants. “Yes,” I said looking down at my faded denim. They’d been in my wardrobe forever. “Those are in,” she said. They never really went out for me. I LOVE flared jeans. Especially when the hem is a little long and I pair them with my 2”clogs to give me that legs-for-days-look (even though I’m only 5”4”.)

So if you still have your Y2K faves in your closet, like low rise jeans or a slip dress, think about why you want to wear them. Do you still love them? Or do you think they’ll make you look cool? Be truthful!

Does It Fit?

Next, you must determine if you’re confident and comfortable in the trend. This means it’s time to try it on. Put on the garment and see if it meets your basic comfort levels. Raise your hands if it’s a top. Crouch down if it’s a pair of pants. Walk a bit if it’s shoes.You must be able to move freely while wearing the trend. Otherwise, it doesn’t fit.

Those are just the physical components of feeling comfortable in a garment. Then there’s the emotional aspects.

“It’s hard to be confident when you’re trying to be someone you’re not.”

Does the trend allow you to still feel like yourself? Or do you feel like you’re playing a character? Getting into costume can be fun. I’m all for an extravagant self expression. But don’t pretend to be somebody else. It’s hard to be confident when you’re trying to be someone you’re not.

Look Good, Feel Good:

Once you’ve decided the trend still fits, and you feel confident and comfortable, it’s time to decide how you look.

Get out your camera and take a selfie wearing the trendy item. I suggest using a photo instead of looking at yourself in the mirror because the picture allows you to see yourself more objectively. Do you think you look good? Tune into your body to get the answer  — it always speaks the truth. Also, the mind likes to play tricks sometimes. It may fool you into wearing something that you’re not fully comfortable or confident in. The way to know if your mind is tricking you is to pay attention to your thoughts.

Not Feeling Confident Or Comfortable:

If you find yourself thinking something like:

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

This is your mind trying to get you to wear something that you’re not comfortable or confident in. You’ll notice this trickery 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 trend. If you are happy with how you look and there’s no sneaky thought trying to get you to hide, then wear it! It’s all about feeling confident and comfortable because when you do, you can wear anything you want.

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!

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About the Author:

Elysha Lenkin helps women express themselves through fashion so they look current, feel confident and stay true to themselves. For over 20 years, shes styled commercial shoots for a wide variety of well-known brands, celebrities and publications including Carrie Underwood, Serena Williams, Tina Fey, and O, The Oprah magazine. Herweekly blog provides inspired style tips and insider tricks that make fashion fun and approachable, helping her clients show up with more confidence in their lives. Take her free quiz to Find Your IT Factor and Discover Your On-Camera Style here: https://elyshalenkin.com/on-camera-style/

Learn more about Elyshas holistic approach to personal style here: https://elyshalenkin.com  and follow her on Instagram here: https://www.instagram.com/elysha_nyc/