In recent years there’s been a backlash to the outdated saying, “dress your age.”
It comes with really good intentions: wear what makes you happy, wear your old items if they still fit, celebrate you no matter your size, etc. etc. etc.
It all sounds great and uplifting doesn’t it? But despite it’s good intentions, I think “dressing your age” is actually really important and perhaps it’s time the phrase itself needs a rebrand.
I’ve styled over 150+ women in the last few years, all of varying sizes, shapes, cultural backgrounds and ages. What they all have in common: they care about how clothes look on their bodies.
As you age, your body changes. As fashion moves on, trends change. A lot of Xillenials have told me:
All I can find at the stores are crop tops now!
There’s plenty of options “in trend” that are outside of what Gen-Z is wearing that is appropriate for a 45 year old professional woman, you just need to know where to look. Or perhaps… and I tend to say this as playfully as I can:
Maybe we shouldn’t be shopping at the same places you did when you were in your 20’s?
On the body front, I think a lot of us Millenials or Gen-X’s have this thought that anything tight and form fitting — think Hervé Léger Bandage Dresses, Roland Moret Sheath Dresses, to name a couple — are the pinnacle of style. And for a time, it was.
But just like our tolerance for a wine and cheese dinner can only last so far into our 30’s, super form fitting bandage dresses didn’t exactly stand the test of time. More importantly, it doesn’t stand the test of being flattering on all body types.
Personal story time! It’s related, I swear:
In 2008 I worked for a small NYC designer who made dresses for socialites. His clientele: mostly 50’s and up. One time we had a trade show at Saks Fifth Avenue — and that’s where I learned that Ru Paul is extremely stylish and glamorous even outside of drag — and we were set up next to, you guessed it: Hervé Léger. Me, being my 23 year old self was so excited, but I had to do what I was there to do: sell conservative gowns to our Upper East Side, gala-attending wealthy crowd. But what I noticed was interesting: so many people, even the “younger” ones in their 30’s and 40’s would walk by Léger and say “there’s no way I would be comfortable wearing that,” and would gravitate towards our little booth and others that sold more wearable options.

Just because something is trendy and readily available doesn’t necessarily mean it is stylish on you. Like the crop tops my Xillenial clients keep mentioning. But what they fail to understand is that every clothing brand, from Shein to Gucci is going to make new clothes every season. So there are plenty of options, in fact I’d say there’s too many. You just need to know what to look for.
As my clients age they care less about the opinions of others and how they personally feel. They might not feel good showing certain parts of their bodies. Or they are nervous I am only going to show them the dreaded crop top because that’s all they are seeing at the stores. And they pleasantly surprised at what I am able to find them that makes them feel good, feel stylish and most importantly: feel like themselves at their current life stage.
There’s also a size element, which can get very sensitive when clients own really beautiful clothes they no longer fit into. But it’s better — both mentally and physically — to start buying sizes to match how your body changes with age. When you’re paralyzed by wanting to stay a certain size and fit into those older items, you get paralyzed in that timeframe of trend and start to look dated. Which ironically, can make you look even older. I’ve seen it happen many times. Your style shouldn’t get stuck by your size. Size is only a limitation if you choose it to be. Ask yourself:
“Even if I could fit into this again, do I want to wear it?”
As our bodies evolve, so should what we wear. And it will evolve, to some degree, of what is trending, but it also needs to evolve to fit your changing lifestyle and body. There is no denying we will age. That’s life. So why not embrace trends that can still make you feel beautiful outside of it being related to the shape of your body?
And finally… what gets less attention in the “dressing your age” debate, is the budget.
I don’t know about you guys, but I certainly will spend more for fresher foods, time-saving options and better coffee.
If you are growing professionally in your 40’s… your wardrobe should match that. If there’s nothing wrong with experience and age, in fact, we get rewarded for it (they certainly reward men for this, don’t they?) — is it so bad to start dressing that way?
So here’s to dressing our age, and feeling great about it.
TIPS: If you struggle to find trendy items that also suit your age, you’re likely not looking in the right places. Step outside of the stores you typically shop at, or step deeper into them - go beyond the front displays and into the racks. Adjust your expectations of quality: Forever 21 isn’t meant to be forever. Don’t EVER click Revolve.com’s “best seller” list. Find smaller brands that match your personal style and make the same types of styles over and over vs a brand like Zara that’s constantly bringing in new. Most importantly: try new things. It can surprise you.
Sera aka The Reoutfitter
Before I even opened the article, I had Hervé Lérger in my head 😂