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?
Love that jacket on you. It really adds a zip to a simple dinner outing of jeans and amplifies personality!
I love your idea to consult with your inner style…. To take a chance on things you love. Your black and white jacket is gorgeous!
Love that black jacket with the white detail. Looks so nice on you.
Great post. I agree we need to be ourselves with clothing that tells others who we are not the road map made by others. The best always
Jennifer,
Thank you for this post!! I have several older Chico pieces that I love but felt out of place wearing. Guess what? I am going to put them on and wear them proudly!!!
I agree the “algorithm” can cause impulse buys that end up not feeling authentic. I am going with what I love for 2026 and see if I can find my retired over 60 style.
Love the jacket! Very unique and a “stand out” wardrobe piece. Also love the fur vest and your black hat. What brand of hat is that?
P.S. I found the leather fur vest you wore with the black skirt on Poshmark. I love it!
It’s one of my favorite. Good find. The hat is an oldie from Renée NYC. I’m not sure the brand is still making hats.
Love, love, love your new jacket!!
Your jacket was a great timeless find! I like to cleanout my closet every change of season and take my things to our local consignment shop. I let my sales accumulate and at the end of the year use it to buy ONE Fabulous item. This year it was a beautiful vintage fox fur coat that fit me perfectly. l will keep it and pass on to my grand daughters one day. My husband pokes fun at me for my “buy high, sell low” wardrobe but my reply is “everyone needs a hobby”!
What a marvelous hobby 🙂
I couldn’t agree with you more! Style and aesthetics are an individual thing and should be celebrated. The best way to do that is to mix it up and go for it with confidence.
P.S. The jacket is stunning on you! LOVE IT!
Fabulous jacket! It looks custom made for you. I thrifted a Ralph Lauren jacket a few years ago from a charity thrift that I wear constantly. You never know what you might add to your wardrobe until it jumps out and grabs you. No regrets.
Love the jacket! And I really enjoy deconstructing great outfits – this would be fun to do
I love decontructing outfits too so I will share some here. Thanks Anne!
Bravo! Thank you for pointing out the fact that the algorithm is driving fashion choices and everyone seems to be dressing alike! At this age, we should all be wearing whatever makes us happy. I love that jacket, and you look fantastic. All the best to you!
Bethanne
Thanks!
That new jacket looks like it was made for you! A great start for you on finding some new ways to express yourself.
As for influencers/algorithms and everyone looking alike…….before this hit “personal style” I saw it in home interiors. I first noticed what I called it the “Pottery Barn” effect in the late 1990s. All woods were brown, with simple lines, and all upholstery was beige. That was before algorithms, and I thought it was because furniture is expensive, but no one is afraid of beige. People were ordering furniture from catalogs and didn’t want any negative surprises. And now 30 years later, most interiors look pretty similar to each other.
Are we afraid of individuality?
Interesting! I know exactly what you mean by the Pottery Barn effect. Finding alternatives seems harder and harder these days.
Jennifer, In the sea of beige interiors, I call our home decor “world tour” because it is colorful, traditional, eclectic and many items did come from travels. Maybe I need to adopt that thinking to personal style?
Yes, it can be fun!
Excellent advice! Thank you.
I really like what you are saying here. Too much trending is going on. I feel like at my age I can’t keep up and I really don’t care to. I have a lot of unique jewelry that I’ve been thinking of wearing more often and not saving it for good. Thanks for reminding us to be ourselves.
This is so refreshing! I am so tired of seeing the same looks shared by “influencers” and stores. People seem to be afraid to stand out in any way. I was at a coffee shop on Saturday, and nearly every woman there was wearing a version of the same outfit.
Yes! That’s what I’m seeing and it’s so boring. It reminds me of high school when every girl wanted to look the same.
I am so in love with that jacket! Good job, you look fabulous! And thank you for saying what I’ve been feeling a lot lately – everyone looks the same. I’ve been on the hunt to add more color to my wardrobe, so now I’ll also be eyeing clothes that feel more “me”. Thank you for a great article!
This post hit me hard! I’m so timid with unusual items and never buy anything that isn’t in my usual string of uniform items. I love what you did with the jacket, which is gorgeous, and it nudged me to take a step into the “wild”. I may start with a smaller item but I will take that step when I find that unique item!!
I’ve been in a rut with my things as well. My closet clean out really drove that point home.
I adore your “find.” What a lucky girl. Your post today speaks to me. Thank you.
I love what you did with new black jacket……I think you did you and let the jacket stand on it’s own and be the focal point (no competing pieces). I love your faux fur vest with the hood…….I’ve been wanting something like that but not that color. I think if you played around with your styling you’ll get what you’re aiming for.
Good luck……