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?
My daughter loves to “thrift” shop and has found some items that really reflect her 20-something style. Your jacket reminds of that and looks amazing on you!
I agree on the barrel-legged jeans; I’ve yet to see someone that didn’t look silly in them, even the tall, thin models. There are some ideas that should just stay as ideas…
You look great in your new/old jacket! Enjoy it. You and Pamela Lutrell are the only blogs I read. You do “influence” me. I enjoy your humor but also your style Jennifer. I guess I have lived long enough to know my style from what is trending and just wear what I feel comfortable in and enjoy. You seem to do so as well. I think we change our style over time. Sometimes it is as simple as body changes. As we age, our waist thickens even if our weight stays the same. So because that is my problem, I no longer tuck. Because I lived my entire work life in scrubs and sneakers, my style is simple, comfortable and casual without being sloppy. I love neutrals like pale grey, oyster white especially in linen for the summer. But I tend to live in tee shirts, plaid flannel shirts over the top or a sweater, love Quince, and jeans. I live in rural mountains of Colorado and make my own fashion statement. Where we live has a lot to do with what we wear. I just love reading your blog Jennifer.
I totally agree about our location being important. I often dress differently in Vancouver than California.
What a nice looking jacket! I would like to be a little more daring, too, but worry I’ll buy something that I’ll regret (which has certainly happened in the past). I’ll try your advice!
Love your posts!
Jennifer, I love this so much. My mother was a Thrifter and she often made alterations to things to make them more unique for her. She was often told how stylish she was. I totally agree with your thoughts, and I’m going to try to be more intentional in finding the “unique “ and not buy unless I love something. Not because someone influenced me.
Thank you for this post – it really woke me up. I’ve been dissatisfied and bored with my wardrobe – pants sweater necklace accompanied by a boring bag – and I can’t find anything I want to purchase. I’m going shopping today and I plan to look for the unexpected items that feel and look good on me. Thank you for the boost!
I’ve been terribly bored with my wardrobe too. I hope you find some unique things.
Love this article. I am not sure if I am listening to the algorithm or I just go to the same retailers, but I would like to change it up a bit as well. I am retired so my wardrobe has changed. I have too many casual pants that are practical and I can take to travel with but then when I go out to dinner, my outfits seem blah.
I love the jacket on you. That is a simple outfit but you added a statement piece.
Appreciate the comment on the sameness. I noticed when attending grandson’s flag football games a few years ago most of the moms were wearing the same outfits including hat. It was a Instagram moment. Now attending my granddaughter’s high school dance competitions that draw teams from the whole state I see pockets of whatever the outfit of the day is. I remember reading my magazines over and over as a teenager. I struggle these days putting new outfit together due to cost and having lost some weight seems to fit.
What a find! That jacket is beautiful and it flatters you. Yesterday I saw a woman who looked to be in her middle 70’s (hard to tell) wearing an emerald green fur coat. It hit at mid hip on her and looked so beautiful and unique. I complemented her on it. She told me she got it at a second hand store. She is a perfect example of the type of woman you described above who does not ask permission. Good advice. I’m going to have to hit some second hand stores.
Jennifer, Love your vintage knit jacket—it looks great! I’m trying to move beyond my perception of a “basic” style, and your example inspires me to start with a vintage piece. Pairing a basic black anchor with unique trim and simple accessories creates a look that feels both accessible and stylish. I admire well-dressed women who break the basic rule and want to focus on becoming one myself. Thank you for sharing!
I want to become one too! So much more fun than following the pack.
This post was so spot on. In the past few years, I have been buying only what I can say to myself ” do you love this ?” Many times the answer is no. I feel that some of my older pieces are far superior in quality than some of the new items out there. To be honest I usually receive more compliments on my older items that I do love.
That jacket you bought is beautiful on you. Along with the pearl necklace.
Things I pull from my “wardrobe archives” are much more interesting. Sadly, that means I also can’t link them for readers.
I love love love the jacket!!!!! So glad you are having fun being back little more daring with your clothes. Not sure how daring i am but I have always loved colors, plaids and prints thanks to my parents. Glad you are seeing interesting women. It is cold here in Michigan so only seeing coats and boots right now. Not very exciting. Lol! Enjoy your jacket!!!
Love your comments, and the jacket! I find that I am happiest with my outfit when I have a statement piece, something that is just different. In the 80″s it was wearing a dramatic pin/brooch with my conservative suits, it was a conversation starter. Thanks for the reminder. Have a blessed week.
I loooove the jacket. I would have bought it in a flash too. Would look amazing with a leather skirt, or jeans, or whatever. I once bought a 700 dollar St John knit sweater on consignment for 70 dollars. Still have it, it’s a classic navy blue that will never be out of style, like a sweater blazer. These things are what makes consignment shopping worth while!
I refuse to look like everyone else. I want to stand out in a classic, modern way. But barrel curls, big lips, overly made up skin and eyes, those sneakers, that purse-nope, not doing it. I’ve lived long enough to earn the right to be different in thought and action.
Your last sentence says it! We’ve all earned that right.
AMEN!!!!
I have 2 pieces of jewelry that always provoke conversation. Both have a story and that’s why I love them. One is my mom’s baby ring, small, simple beautiful. The other is my Nursing Pin. I know it sounds weird. It is solid gold, round, has beautiful detail and been in my jewelry box for 45 yrs. One day I had a crazy idea to turn it into a pendant and I love it!
Brilliant idea!
Wow Jennifer, such wise words, beatifully written. You have inspired me!
So glad you bought the Oscar jacket. It looks great with the jeans, but I can also see it for dress up with a long skirt for a special night out. Also like the faux fur vest. Both items are my style 😊, Would wear both.
Love this post and the jacket. We all have that special story to tell in something we love to wear.
This is the post I needed to read! I have felt my style has been in a rut especially since I retired as a teacher a year ago. No longer wanting to wear the “teacher look.” Read a suggestion to create a board on Pinterest of style that “spoke” to me. Everything looks the same just as you described in your post. Forget Pinterest, I’m just going to start wandering into stores I haven’t been to in a while and search the wonderful links you share.
That’s why I love thrift/consignment shopping! It’s a treasure hunt! The only risk for me is that I know if I want it, I need to purchase now, because it likely won’t be there when I go back. I also do this with household decorations. For Mardi Gras, I bought several large ceramic serving pieces at our excellent charity shop, used them for the party and donated them the next week for the next treasurer shopper!! And the charity wins!
Oh Mudra, how clever of you! Great idea.
Jennifer, I looked at the photo and said- Now THAT is a beautiful jacket! Then I read who designed it. Always beautiful quality pieces no matter the year/season. Lucky you. My daughter posts on IG and her most original outfits often include a “ vintage “ piece from my sister. Everyone’s capsule wardrobe of cream & navy is getting a little boring. Here’s to an exciting new year!
I love that jacket- what a great find. I can see it worn with a long flared black skirt and boots. That looks like something I’d hang on to forever.
And I have a long black skirt from my travels last year! Yes, it’ll be perfect.