The Flop

Welcome back to The Flop - your cozy corner for demystifying AI with warmth, wit, and a dash of whimsy!

This week, we’re talking about something fun: how AI can help you look better. Yes, really. It can suggest sunglasses that suit your face, help you plan outfits for actual weather and real-life events (not just Pinterest boards), and even recommend makeup looks that don’t require a YouTube degree in contouring. Let’s dive in!

🐰 Down the Rabbit Hole

Can AI Be Your Stylist?

Maybe you’ve seen apps that let you try on makeup or sunglasses with your phone. Or maybe you’ve heard that AI can suggest colors, outfits, or haircuts. But how does it actually know what works for you?

The answer lies in two terms you don’t need to memorize, but might enjoy dropping casually at dinner:

🔎 Computer vision
This is what lets AI “see” and interpret images. It’s how your phone recognizes your face, how Google Photos knows that’s your dog, and how a style app knows you’re wearing a crewneck and not a cardigan.

📐 Feature extraction
Once the AI sees an image, it breaks it down into data it can use - like “this jawline is angular,” “this skin tone leans warm,” or “these pants are not doing what they promised.”

It’s like having a very observant intern who’s been trained on millions of examples and is now eager to tell you which sunglasses are “scientifically” your best match.

🎯 Where this works really well:

• Sunglasses fit: Suggests frames that balance your face shape

• Color picks: Spots undertones and suggests flattering shades

• Silhouettes: Notices what styles you gravitate toward

🎭 Where it gets a little dicey:

• Lighting lies
  A yellow-lit bathroom selfie might trick the AI into thinking you’re warm-toned when you’re actually neutral or cool.

• Bias in the data
  If the AI was trained mostly on lighter skin tones or Eurocentric styles, it might give less helpful suggestions for people with darker skin, natural hair, or different cultural aesthetics.

• Taste ≠ math
  Just because a certain look mathematically flatters you doesn’t mean it’s your vibe. You’re allowed to love the round frames.

So yes, a robot can technically be your stylist—but only you know what makes you feel like you. This week’s hack is all about using AI as a helpful sidekick: to make suggestions, spark ideas, or rescue you from closet overwhelm.

(Rosemary Cloud continues to serve her signature look: soft neutrals, natural texture, and an air of complete indifference.)

🛠️AI Hack of the Week

Let AI Help You Look Good

You don’t need a stylist or a Sephora budget. These simple tricks can help you get practical style advice using tools you already have.

👓 Find Your Ideal Sunglasses

Tired of trying on 18 pairs and wondering if your face is “too round” for aviators? AI can help you skip the guesswork. (Thanks to Ann for this great hack!)

Go to Gemini (Google has all my photos already so I worry less about privacy) and say:

The AI analyzes your features - face shape, skin tone, proportions - and offers suggestions for shape and color.

Then, try on different sunglasses and ask Gemini which pair/s look the best on you. It’s a great cheat for when you’re bestie can’t go shoppign with you!

👗 Ask What to Wear (Using Photos of Your Clothes!)

If you’ve ever looked at a full closet and thought, “I have nothing to wear,” this one’s for you.

Step 1: Snap a few photos of what you actually own.
Step 2: Upload them to ChatGPT (or another image-enabled AI tool).
Step 3: Ask:

You can even add context:

The AI will scan your photos, identify what’s there (jeans, button-down, floral skirt), and offer outfit pairings, layering suggestions, and color combos that make sense.

Bonus: It won’t shame you for owning three nearly identical gray sweaters. (They’re different. We know.)

💄 Dupe That Lipstick

You love a certain lipstick but it’s discontinued, sold out, or costs more than your favorite coffee order. AI can help you find a lookalike.

Try asking:

ChatGPT can compare ingredients, shade descriptions, and user reviews across brands - from Sephora to Target- and offer alternatives at multiple price points.

It’s like asking a beauty-obsessed friend who’s also annoyingly good at Google.If you do want to use AI but keep things more private, here are three ways to make your chats safer, from least effective to fully locked down.

🧠 Why this matters:

This isn’t about chasing trends or impressing strangers on the internet. It’s about feeling like yourself but with a little more ease, a little more confidence, and maybe fewer pre-event meltdowns.

AI isn’t going to tell you who to be. But it can help you show up as the version of yourself that says, “I’ve got this” - whether you're headed to a wedding, a job interview, or just back-to-school drop-off in pants you won’t regret.

🗳️ Nosy Rosie Wants to Know

Quick Poll: Would you let AI be your stylist?

Last Week’s Poll Results:

👋 Until Next Week

Thanks for being here. I know your inbox is a busy place, and I hope this one made you feel just a little smarter and more prepared in this new world of AI.

Warmly,
Ricci

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Last week, we explored how to protect your privacy when it comes to AI.