When my friend Tresi first sent me a link to some Street Style Fashion Week photos from Vogue, she had a valid concern.
I included her message below, and I’m sure many of you can relate, but I wanted to give a perspective on this subject.
Quote of the day: “Many people want to change their lives, but they are not willing to change their choices, and ultimately this changes nothing.” MJ DeMarco
Tresi’s first email was “Seems to me there’s a lot of ironic styling out there – ‘frumpy is the new cool, frazzled lady’, and some bonkers mixtures of garments.
Whilst I love the return to individual looks and applaud anti-algorithm dressing, I think this can be challenging for anyone, especially if you’re older.
There’s a bit of me that says there are some trends that really should be left to people in their teens and twenties – I would hate to rob them of rebellion!
You know that I’m not scared of trying things, and don’t do rules, but I’d appreciate your steer on how to pick styling that looks up to date without looking like I’m off to a fancy dress party, or worse still, like I’ve raided my attic wardrobe!”
If you want to see some street style from fashion week, here are links to those sites. I always like to remember that these are not the only looks, but the ones that the site wanted to publish.
–London
–London via British Vogue
–Milan
–Street style trend. This is one that Tresi and I decided we loved the last photo, and I recreated it on Saturday of this Daily Outfit post.
The Facts
That question got me thinking because I’ve had the same thought many times in the past. Before I became bolder in my style, I used to wonder why magazines like Vogue showed such crazy outfits. Who actually wears that?
But the more I’ve learned about fashion, especially from following designers and creators, I’ve realized something powerful.
Designers are not trying to dress the masses. They’re trying to inspire creativity.
Designers and editors want outfits that are interesting, not something you’d see on 100 other women at the grocery store.
Should it be the energy women over 50 embrace? Or should we leave it to the youngsters?
-Lace
What Is Street Style Fashion Week?
If you’ve ever scrolled through photos from New York, Paris, or Milan during Fashion Week, you’ve probably seen a mix of jaw-dropping looks: dramatic layers, bold prints, sculptural silhouettes, and unexpected color combinations.
Street style during these events isn’t just about the runway shows. Instead, it’s about what the guests and influencers wear outside the venues. The sidewalks become an unofficial catwalk, full of creativity, playfulness, and self-expression.
Insider tip: Women of our age didn’t grow up with street style fashion week photos splashed all over our screens. Back then, we only saw polished magazine spreads and department store mannequins. The whole idea of everyday women showing off creative, bold outfits really took off once social media entered the picture. Suddenly, style wasn’t limited to models on a runway. It became something real women could play with, interpret, and make their own.
The only street style we had was seeing what other women were wearing at our workplace or grocery store. And while that can be inspirational, social media has made this idea international and inclusive-not just for thin women in their youth.
I like to think that street style fashion week has become a laboratory for ideas. It’s where trends start, evolve, or get tweaked into something wearable.
Why Older Women Should Pay Attention
While I realize that most of us are not walking down the streets of Milan anytime soon or trying to make it onto a Vogue street style roundup, it’s an incredible way to get inspiration.
Before you look at a couple of photos and think they are too crazy, PLEASE stop and ponder. Because I believe that the purpose of looking at these photos isn’t to copy the look head-to-toe, it’s to see what’s possible.
Even if you don’t have a similar item, the artistic ideas abound.
Insider tip: It’s like a real-life view of Pinterest. While I love getting inspiration from Pinterest, the disadvantage of Pinterest is:
1-It is an algorithm and thus shows you the kind of photos you like and save.
2-There are a ton of advertisements on Pinterest lately, which can be annoying.
3-The photos on Pinterest are not always real-time. I see many of my Pins from 5 or 10 years ago. They aren’t the outfits that would inspire me now.
Unfortunately, when we are over 50, 60, or 70, the message tends to be “tone it down.” Somewhere along the way, society decided that our style should fade into the background.
But if there’s one gist I would love us to take from street style fashion week, it’s that it’s never too late to be unforgettable.
The women and men photographed outside those shows aren’t worried about blending in. They’re making a statement, even if it’s only for themselves.
And even if it’s not “your thing”, there’s something beautifully empowering about that.
From “Too Much” to “Just Right”
Let’s be real, some of those street style looks are over-the-top even for me.
But here’s where the magic lies: you can take the idea, not the whole outfit.
The concept is to borrow the energy, not the exact look.
For example, I have a sheer skirt, but have only worn it over another skirt. Why not try to wear it over jeans?
When I first started experimenting more with my wardrobe, I realized how much fun it was to push my comfort zone just a little bit.
That’s the lesson from street style fashion week for us “normal” people looking at the photos. You don’t need to copy it piece by piece and look outrageous. Instead, how about having a goal of looking original?
Remember when we started wearing no-show socks and thought it was weird. Now it’s time to evolve back to showing our sock collection.
Frumpy vs. Interesting
This brings us back to Tresi’s original question:
Would women of a certain age look strange or frumpy if they tried these kinds of bold looks?
My answer: Yes, no, and then again maybe.
Because when I asked my friend’s kids about what made a woman look frumpy, it had nothing to do with “over the top” style. It was more about basic and boring.
That lends itself to the ‘no’ category.
But if you “copy” something that you don’t feel good in, it’s going to show. Thus, the ‘yes’ category.
It may come down to the fact that you need some self-confidence BEFORE you try something outside your comfort zone. And how does one get that?? That’s the million-dollar question.
Insider tip: The one thing I know is that if you don’t try to get confidence, it’s not going to happen, just like the quote of the day. Everything in life is practice, practice, practice.
So the key isn’t to dress like a woman photographed in one of these articles about street style fashion shows. It’s to dress like the boldest version of yourself.
Need more ideas about not being frumpy?
–What to wear with capris
–Wearing brooches without looking frumpy
–Long skirts
– Why not add bows to a solid colored dress?
How to Translate Street Style to Everyday Life
Let’s get practical. Here are a few ways to channel that fashion week creativity with what you already have in your closet.
1. Mix Unexpected Pieces
Pair casual and dressy items together, such as sneakers with a fancy skirt or a graphic t-shirt over a cocktail dress. It’s the high-low contrast that gives an outfit edge.
2. Play with Proportions
Oversized isn’t just for the young crowd. Try wide-leg pants with a fitted top or a boxy jacket over a slim dress. The mix of shapes adds that artsy vibe you see in street style looks.
3. Experiment with Color
Fashion week outfits are bursting with color and often in combinations we’d never think of. Try pink and red, mustard and teal, or even lilac and olive. You don’t need to go head-to-toe bright; just add one bold element.
4. Accessorize Like You Mean It
Street style stars are masters of accessories. Think statement earrings, chunky belts, layered necklaces, or colorful bags.
Accessories are a low-risk way to play by making your outfit look intentional.
5. Don’t Be Afraid of Volume
Many women shy away from oversized sleeves or flowy silhouettes, worrying they will “add weight.” Forget that rule. Looking taller and slimmer won’t make you unforgettable or a better person.
Insider tip: Reevaluate those items that you would NEVER wear, be it ruffles, pleats, or such. It is just material sewn in a certain way. I always think we should be more open to all the styles. Many times the ONLY reason it doesn’t “feel” like you is because you haven’t given it the old college try…sometimes that means more than once.
-Embroidery on chartreuse
-Furry collar
The Real Lesson from Fashion Week Street Style
Here’s what I’ve come to believe:
Fashion Week isn’t always about what’s wearable; it’s about what’s possible.
Insider tip: It’s the same idea when you see someone out in public with pink hair that you think looks crazy. I would ask you to stop being judgmental and applaud that person’s uniqueness instead. While it may not be something you would want for yourself, luckily, we all get to be distinctive in our own way.
Possibility is a playground for creativity. It pushes boundaries, breaks rules, and reminds us that style is meant to be fun.
And if we want to stay youthful, not just in looks, but in spirit, then embracing playfulness in our wardrobe is one of the best ways to do it.
So next time you scroll through photos of street style fashion week, I beg you to find at least ONE outfit that you could pull an idea from and make your own.
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