How To Know If You Need A Wardrobe Overhaul: Expert Stylist Advice

During a recent personal styling session, my client asked for advice on which items to discard. She had some sweaters that she really loved, but they were starting to pill, and she wasn’t sure what to do about her cobalt blue spring jacket with the oversized lapels. She wondered if it was still in style. On top of that, she was sick of wearing the same old basic tees every single day. They had become her go-to look, but not intentionally! She knew she needed a wardrobe overhaul.

Do You Need A Wardrobe Overhaul?

If you can relate to my client and find that your clothes are wearing out, going out of style, or no longer inspiring, it’s probably time to revamp your wardrobe.

But what if you’re not in her situation? What if your clothes are still in good condition, they’re timeless pieces, and you can create plenty of outfits? You might not think you need a fashion update. Well, those aren’t the only signs that it’s time to freshen up your style. Keep reading, for 3 other ways to tell if you’re due for a fashion update.


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woman looking at her wardrobe

1. Ugh, Nothing Fits!

It’s completely natural for our bodies to change over time, but that doesn’t make it any less frustrating when our longtime favorites don’t flatter or feel comfortable anymore! It can be a real stress to get dressed when this happens.

That’s why you want to update your wardrobe with styles that fit well and highlight your best features. (Click here for a free style guide to determine your body shape.) I was just looking at an old photo of one of my clients whose button up blouse was puckering between the buttons which indicated that it didn’t fit her properly.

Although this may seem like a minor styling issue to some, it made her self-conscious and distracted her from being present and focused. We want our clothes to feel effortless so that once dressed we can forget about them and focus on our day with confidence.

white shirt that puckers in the front

If you decide to do a wardrobe overhaul because your clothes don’t fit, remember that clothing sizes can be all over the place. You might be a size 10 in one brand and a size 14 in another. So know that it’s not about the number on the tag, it’s about how you feel in the clothes you’re wearing. Look for pieces that make you feel amazing – that’s what matters most.

2. Yay! You’re Taking Your Career To The Next Level!

If you’re in this situation — congrats! Just a heads up though, it’s easy to overlook the need for a wardrobe overhaul when you’re swamped with new responsibilities. While it’s tempting to stick to your old outfits, they might not reflect your recent success.

Is your work wardrobe too casual?

One of my clients was promoted to a new position and quickly realized that her current wardrobe was too casual for the role. She ended up attending meetings in clothes from her previous job, which made her feel unprepared and out of place.

Is your work wardrobe from the past?

Another client of mine, after being promoted to partner at her law firm, discovered that she had never taken the time to update her wardrobe. As a result, she found herself wearing outfits from her early years that reminded her of her less experienced self. This wasn’t the vibe she wanted to convey during important depositions!

If you want to exude confidence and make a great impression from the get-go, consider a wardrobe overhaul to reflect your current accomplishments.

closet stuffed with clothes fountainof30

3. Help! Your Wardrobe is Overwhelming!

When we think of a wardrobe overhaul, we usually focus on buying new clothes, but that’s just one part of the process. It’s just as important to edit and declutter what you already own.

Do you wear the clothes you own?

One of my clients LOVES fashion and spends a lot on clothes that catch her eye. The problem was that most of these clothes didn’t really match her style and ended up adding to the overwhelming pile of clothes that slowly were taking over her entire house. When she finally decided to take action and overhaul her wardrobe, she understood that she needed a solid plan to identify her unique style and revamp her wardrobe accordingly.

Why not work with a stylist?

We spoke recently and she said how excited she was about working with a stylist. Apparently, she’s been wanting to do it for ages, but always held back because she didn’t think it was worth it.

Can you relate? I totally get the guilt of spending money on myself, even if it’s something I really want. I’ll happily spend thousands for my kids’ braces, but when it comes to my own satisfaction and happiness, I hesitate. Crazy, right?

Your Wardrobe Overhaul

So what’s your plan? Are you ready for a wardrobe overhaul, or are you content with your current closet? If you’re thinking about going for an update, especially with the change in seasons, the first thing you should do is figure out your personal style.

Luckily, I’ve got a free quiz that can help you identify your preferences and decide which styles you want to incorporate after your overhaul. Click here to take the quiz and get started!

– Elysha Lenkin

Photos: Canva Stock

Elysha Lenkin is an expert personal fashion stylist whose mission is to help women stay true to themselves while looking current and feeling confident. Throughout her 20 year career, she has styled women of all shapes, sizes, and ages, including Carrie Underwood, Tina Fey, and Serena Williams. If you’re interested in putting together a fresh outfit with your existing clothes, be sure to check out her free style guide here!

And for more style tips and inspiration, head over to Elysha’s website: or follow her on instagram: @elysha_nyc.

You may like to read more of Elysha’s styling posts on Fountain Of 30 like Am I Too Old To Wear That Trend? 3 Questions To Ask and Style Rut? 3 Reasons Your Clothes Don’t Work (And What To Do About It).

Are you following Fountain Of 30 on Facebook, Twitter, Instagram and Pinterest? We’ve got lots going on, so join in on the fun! Subscribe to our newsletter here.  You don’t want to miss a post and promise not to bug you to death. Join our Facebook Group called Growing Younger where women discuss everything good and bad about being over 50. Additionally Lauren hosts a bi-weekly podcast called Beauty is a Bitch! and an Instagram Live series called “Growing Younger Gabfest with Lauren.”

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