Monday Musing: Is the Algorithm Destroying Personal Style

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?