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?
Yes, I have the algorithm fatigue. I have always loved to grab pieces at a boutique, but all of the boutiques near me that I used to frequent have closed!
I tend to “fall in line” with the catalog looks and the sales during the Christmas season, but then I have too much of the same thing come January! Same thing happened this year. Creature of habit!
I did buy a satin skirt in December (QVC), not really being certain that it was my style. It fit so perfectly and I love it so much (wore it on NYE), that I ordered another one! It’s worth it to take a chance on something different, just like your jacket, which is fabulous and looks fantastic on you! Great find!
Love the jacket- looks great on you. Showing you have a great interesting character- and very classy taste.
Way more fun too!😉
I love your thought process, Jennifer. To “be unique” in a good way is a dream – hard to construct in real life. I’m quite senior and happy when I’ve achieved the “shes well put together” look. Mostly it’s the uni-look, the column of color. But, scarf around my neck, long sweater, or chic short jacket, or snappy necklace . . .? You do give me courage to try, and I appreciate your honesty. Have a lovely week,
I think trying something new is a fabulous goal.
Oh my gosh that jacket it amazing ! I’m so glad you bought it. It looks wonderful on you. I’m sure every time you wear it you will have a wonderful memory and a great story if you choose to tell it ! What a lucky find.
I love to resale shop and I have found some pieces that I just love. They are not new or trendy but they are me.
I loved this post and I hope you have many more adventures to tell us about in the future.
A while back I realised that my unidentifiable home style was “the collected look” (as described by a blogger) brought together cohesively over many years. Why oh why couldn’t I have managed that with my wardrobe, instead of which there was a constant outbound trip to the thrift shops. In some defence, weight management played a large role as well as retirement. But still, very much older and wiser, I’m resolving to now find the collected look for my wardrobe. Great piece, thank you.
You really lucked out with that beautiful jacket – and I think it looks amazing on you and the simple way you styled it.
I love the faux fur vest.
It looks very stylish on you.
The black jacket is great; unique and does not look its age.
What your look for in re-loved items.
I love that vintage Oscar jacket and the personality it gives to your outfit!!
Hello Jennifer love this thank you! I’ve been feeling a little trapped lately trying to keep up faishon wise….and now I am heading into my own independent land and moving away from following advice from fashion guru’s. “I like what I like” is now my motto. Texture and color and fabric is always “my jam” and lately I have reached for a knitted sleeveless sweater I made from a Kasse Fasset book(incredible knitter) in blues and greys about thirty years ago!! Looks great with a denim shirt. And makes me happy:)
Have a beuatiful week.
Kasse Fasset patterns are amazing!! You must be a very talented knitter Francesca.
I love this jacket, so glad you purchased it. It has enough flair without being overdone. Love black,navy, cream or white together. I must say that I do not write to you, maybe once or twice but I definetly look forward to reading all your information and where items can be purchased and I like that you give alternatives especially since not everyone can spend alot on clothing. I’m very short, I shrunk 4.9 feet now, weigh around 129, a little to much weight for my size but I’m working on it. Petite is the only way to go or my sleeves hit the floor, hahaha. I am much more conscience of what I’m buying so I do not have to return items. You have helped me very much and I so appreciate it. J Jill is my store, they carry just about everything in petite. The stores do not carry alot of petite merchandise but I use their on line buying even with the shipping charge. I also visit the store to look at the styles and fabrics in the regular sizes. They also have great sales, if you wait you can get the item and if not I feel it wasn’t meant to be. If you order in the store the shipping is free. Hope this helps the petite ladies.
Thanks Mary Ann. You are quite petite so I apreciate it must be a real challenge to find the proper fit.
Absolutely love this ….exactly what I think. That Oscar piece is a keeper. I dress 95% from thrift and I have some exquisite pieces. A pair of leather booties from Spain I paid 5$ for 20 years ago that are classic and I get comments every time! Adding a piece to a chain is brilliant too. As is adding brooches to neck pieces.
I’m going to try more things with my brooches too.
I love that jacket. But I will point out that I recently saw a navy cardigan/boxy jacket trimmed with white blanket stitch both at Chicos and Talbots. I love navy and would have purchased it if it wasn’t boxy. My point here is that maybe some of it means to follow the algorithim a little bit? Your jacket is nicely fitted and elaborately trimmed with white, but it does remind me a little of this trend…
Styles do always come back around so I’m not surprised at all. That’s not following the algorythm, thats smart shopping by recognizing what you really love!
This really resonated with me!! Thank you for this inspiration to wear what you love and not what everyone else “should” be wearing!😊
I love love love that jacket and the thought behind your purchase of it! Definitely going to lean into this idea!!
I love this post and the jacket! I had a similar experience last spring when I found a brightly coloured Harvé Benard jacket in our local thrift store. I had never heard of the brand until I looked it up online and I initially passed the jacket by because I don’t usually wear anything that bright. It kept calling out to me though and when I found a sleeveless top that coordinated perfectly with it, both pieces came home with me. I feel like a million dollars wearing them and have had many compliments.
What a wondr ful find! And to think that it actually fits you, even better! The rare finds I’ve made in consignments shops have always been too too big or too long for my frame. I do have a furry vest similar to yours that I bought 13 years ago on a bike tour in Italy. I have NEVER worn it. It’s gray with a bit of burgundy, perfect colors for me. You have inspired me to take it out and get some wear out of it during our unusually mild winter. I can make it work!
Yay! I’m happy you’ll wear it. What a great souvenir.
I learned a lot about style with an outfit a friend wore. I did not like any piece she had on. Wrong colour, style etc for me. But she looked fantastic. I learned I want to ‘look great’ rather than ‘I love your top’, which I think means they are thinking if it would work for them.
I agree that we start to see things and then end up buying them. I love 2 piece matching loungewear and the idea of ponte knit pants. They look good on me when I put an outfit together but I am not always comfortable as I feel like I am in pjs! I guess I have also learned looking good doesn’t always mean it is my style!
Great observation Barb, thanks for sharing it with us.
Bravo to you for this blog today! I follow several fashion blogs and you are the only one who consistently is true to your style. The rest are all over the board to what sells and what is trending. It is never consistent and true. Thank you for today’s post and reminding us to be true to our style not what others think we should be.
Jennifer in Port Angeles, WA.
At age 68, this is where I’m finally at. Just wear what I want whether it’s in style or not. It’s usually not. I’m working on not buying the “in” thing just to get rid of it a year later. I love your jacket and your push to buy it and wear it. Thanks!
I don’t have a great consignment shop near me but I do have a jeweler who repurposes your past and inherited treasures. I now have several pieces that are uniquely me, along with found treasures, mainly rings, that are now resized and in my jewelry box. Don’t forget your jewelry when you reshop your closets!
Yes! I have some pieces from my Granny that I’m thinking of “tweaking”