Monday Musing: Is the Algorithm Destroying Personal Style
Today, I’m rambling about personal style and the influencer industry, which seems to be at war with individuality.
I’ve always been drawn to women whose outfits make them look like they have an interesting story to tell. Not the ones who look “put together” in the Pinterest-perfect sense… but the ones who look like they’ve lived a few chapters you’d actually want to read.
Maybe it’s a unique jacket that’s clearly been somewhere or the jewelry that looks like it came from a dusty little shop in an exotic country, rather than a department store with reward points.
The pieces on these women don’t always match, but, more importantly, they look like they belong on them. Nothing feels overly styled, and nothing looks like it came in a bundle labeled “influencer picks.” You look at her and think, She’s definitely seen some things. Possibly rolled her eyes at them. Probably laughed at the wrong moment. I want to sit next to her.
And maybe because I keep noticing those interesting women, I’m also more aware of the opposite…the ones who are technically dressed “well,” but whose outfits all blur together.
I’ll pass four in a row at the store, see them in line for coffee, or all over the internet, and they’re all wearing some version of the same thing. The same beige coat, colorful Adidas sneakers, and the same “effortless” crossbody bag that’s shown up on so many feeds that it starts to feel like a requirement. You see it enough times and you start to think, maybe I need that too.
It makes me wonder if personal expression is dead… or just wounded by the algorithm. Because when everything looks the same, the instinct is to blend in. You stop trusting your gut. You talk yourself into things you don’t even like and end up with a closet full of “perfectly fine” clothes you never reach for.
But the women who still catch my eye? They’ve stopped asking for permission. They aren’t wearing the “right” thing; they’re wearing their thing.
A Rare Find
I decided to take my own advice the other day when I found a vintage knit jacket in a secondhand shop. It had more embellishment than I usually go for because it looked ornate, and I initially talked myself out of it because it wasn’t “me.”
I chatted with the shop owner, and she pointed out that the jacket had two tags: one from her shop and one from The RealReal. Apparently, one of her consignors regularly buys pieces from The RealReal, wears them once or twice, then resells them locally…a cycle that feels both impressively efficient and mildly unhinged.
Intrigued, I went back for a second look. This wasn’t just a mass-produced garment. It had been cared for. The inner facing had been replaced by hand, and the front hooks had been resewn with extra security. It had a history. The original label had been removed, but the RealReal tag simply read “Oscar” with a string of numbers. I snapped a photo of the jacket, uploaded it to Google, and sure enough, it came back as a 2001 Oscar de la Renta original.
So, I bought it. Not just because of the name, but because the jacket itself had “seen some things.” It had been reinforced and passed through different hands, and it stood in total defiance of the “beige coat” uniform.
One of my style goals for 2026 is to have more fun and dress with more creativity. I wore the jacket out to dinner with a simple black turtleneck, jeans, and booties. While the rest of the look was understated, the jacket made it feel daring… a little “not me,” yet exactly who I want to be. I’m anxious to see what else I come up with.
How to Outsmart the Algorithm
If you feel like your own style has been “wounded” by the feed, here is how I’m learning to hit the reset button:
Stop Asking for Permission: The women who look the best are the ones who aren’t afraid to look “wrong” to the rest of the world. Trust your gut. If a piece pulls you in, but it “isn’t you”…maybe it’s actually the new you waiting to happen.
Audit the “Why”: Next time you’re about to buy the “it-bag” or those trending sneakers, ask: Do I actually love this, or have I just seen it ten times this morning? If the answer is the latter, put it back.
Look for the “Story” Piece: Start small. Find one item like a vintage scarf, a thrifted belt, or a unique piece of jewelry that didn’t come from a big-box store. Let that one “imperfect” item be the anchor of your outfit.
What about you? Do you feel the algorithm fatigue? Do you have a piece in your closet that felt a little “unlike you” when you bought it, but now you can’t imagine letting it go?
That jacket is gorgeous! And I bet it will draw other women to you to chat about how great it looks on you. That’s another potential benefit of wearing a piece that has a history or a story behind it–other women with stories want to hear about yours. Some of my favorite pieces are from thrift stores. I have a Dolce & Gabbana sweater that is easily twenty years old, looks newer than most of my newer cashmere sweaters, and has cost me pennies per wear. And I have interesting conversations with women every time I wear it!
I absolutely do have a couple of those things that just called to me. One is a tie dyed skirt that I got at a roadside pop up, another a scarf that was a gift from many years ago. Fun!
Good Morning Jennifer and Happy Monday! Once again, love your Monday thoughts and love that jacket on you. Great find, its amazing. And I can’t wait to see what else you come up with. I think one can find some unique pieces at Anthropologie.
You’re right! Anthropologie always feels like a treasure hunt for me.
I LOVE that Oscar jacket!!! It’s pieces like that that tell such an amazing story and get compliments when worn! I have. a few pieces like that, including a beautiful knit dress with native american embellishments that my MOM wore in high school! I love these interesting pieces of my wardrobe and I love how different they make me feel! I will never be “supermodel” thin or polished (never by a long shot), but I appreciate my own style, size, and look and the confidence it gives me!!!! 😊
It’s all about the confidence. How fortunate you are to have your mom’s special dress.
The Oscar jacket looks great! What a find.
Jennifer,
Your post is just what I needed to hear this morning! I have been one of your followers for quite some time. I have to say that I love the “Oscar” jacket…not only the way it looks on you, but the confidence you exude while wearing it. Thanks for encouraging all of us to be our authentic selves and wear what we love.
Ginger R.
Jennifer, your jacket is divine. I love to shop at consignment shops to find that one unique piece or accessory that makes me feel special. I once bought a hand embroidered Cape from a woman in Mexico and every time I wear it ( it really elevates a turtleneck and pants!,) I feel so great.
What a wonderful and well-timed post. January is such a good month for reflecting on what’s in our closet and making the most of what we have, adding a little fun here and there. I feel a trip to my favorite consignment shop coming on!
Have fun!
The Oscar sweater is stunning. Over a winter white column would work as well. I have been thrifting for a few years now and find many unique and well made items in my treasure hunts. In an attempt to be more ecologically friendly I started looking at Poshmark, The Real Real etc. now it is just fun to shop! Perhaps this will be a new venue for you?
I love the jacket and would definitely wear it. Have fun with it.
The jacket is absolutely stunning, and you look amazing in it. Not only do I love that you took a chance on it, I love this post. Creativity does seem to have gotten lost in the algorithm. Great observations and I can’t wait to see what’s next. Happy Monday!
Happy Monday
The jacket is amazing and you look wonderful wearing it@
I LOVE that jacket and so glad you went back and bought it! It’s gorgeous and really adds to an outfit. You’re right, I keep seeing the same things over and over again and it gets boring. I love something that pops and might just have a story.
I have a bright yellwool coat. Bought because a loved it never seen anyone with it.
The compliments keep coming and it’s me!
Yay!
Thanks for this inspiring post! I’m shopping the back of my closet in 2026 and rediscovering pieces I pushed aside and taking another look at why I purchased and does it still feel like me.
That jacket is fabulous; yes, be the, “When I am an old woman I shall wear purple and things that don’t go.” Be your authentic self, add a little zip. I tell my high school granddaughters to be hall stoppers, to be themselves so they stand out. Never get rid of that jacket; it is timeless and can be worn a million ways.
What shows on the outside reflects what is inside. I think we live in a world where there is a desire to not only blend in but to excel in “sameness”. From eating at the current trendy restaurant / and what is better than being the one to tell others about it / to finding the best get away …. We feel safe and in our comfort zone. A sort of Stepford wives world. No thinking. Just follow the yellow brick road .
So true Susan. I’m feeling so bored by the sameness I want to shake things up.
I always love your posts and your classy taste. This one was a wonderful surprise and perfect to start the New Year! Now you’ve got me thinking 😀
Yay!
That was a fabulous find and looks amazing on you!
What an amazing jacket. It suits you so well.
Two other items of special clothing came to my attention this week. A newspaper photo of Dyan Cannon in LA, now 88 years old, wearing a simple black top and pants over which she had thrown a version of that LA Anderson Harry Styles cardigan. She looked amazing.
The other was my daughter’s purchase in an outlet shop of a Ralph Lauren weather coat for a fraction of the original cost. Unlike cheaper versions, this was feather weight.
Special clothes are just that, special, and to be treasured.