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This Friday, let’s talk about AI’s latest obsession: getting us dressed. Then, an Old Thing that cleanses both the soul and the keyboard.



Google Photos Wardrobe, left, ChatGPT Virtual Try On, right.
Ever since cave people wrapped themselves in animal hides, humanity has struggled with a daily conundrum: What should I wear?
Finally, the unprecedented computational force of AI has solved it.
I joke. Kinda. This week, Google Photos Wardrobe and ChatGPT Virtual Try On rolled out. Both let you see what you look like in different clothes—no full-length mirror required.
These tools are basically the “Clueless” digital closet dream come true. Except unlike Cher Horowitz, you don’t need some super-special tech setup to see how you’d look in that suit or dress you really don’t want to go try on at the store.
Retailers and apparel brands from Walmart to Gucci have offered virtual try-on tools for years, letting you test-drive everything from jeans to makeup without leaving the couch. But there’s a bigger reason the AI giants suddenly care so much about getting us dressed: money.
Google Wardrobe
Google’s Wardrobe feature is built right into Google Photos. In the Photos Android and iOS app, tap Collections at the bottom. You should see a box inviting you to Build My Wardrobe. Tap it and let the AI rummage through your closet—or your photo library. (To use this feature, Google Photos must be updated and the Face Detection feature must be turned on in Collections.)
The AI scans your photos and pulls out some of the clothes you’ve worn recently or frequently. From there, you can mix and match items and virtually try the combinations on yourself. When I gave it a try, Wardrobe surfaced some clothes and combinations of clothes that I hadn’t thought about wearing in a while.
ChatGPT Virtual Try On
In ChatGPT, search for a clothing item and you may be prompted to upload a selfie or full-body photo to see how the garment or accessory might look on you. You may also see a Try On button beneath a clothing listing.
The tool, which just rolled out Thursday, is clearly still a little rough around the edges. It mostly seemed to put my head on the model’s body. Terrific for my self-esteem, less terrific when the clothes actually arrive. ChatGPT’s biggest strength, though, is that you can just describe what you’re looking for—say, a business-casual outfit for interviewing a big-tech executive—and it will suggest the pieces and let you try them on.
(Full transparency: Glance, a different AI shopping app that offers some similar features, recently sponsored one of our YouTube videos.)
Big money
Google Photos doesn’t directly connect Wardrobe to shopping, though Google Shopping has a similar try-on feature. And it’s not hard to see why these companies are interested in all this stuff. Thirty-nine percent of consumers told Adobe in a survey this spring that they’d used AI for online shopping, and 85% of those users said it improved their experience. Even more appealing to retailers: 69% said AI made them less likely to return what they bought.
If AI can show you how something might look on you—or just inspire you to hit “buy”—that means more sales and potentially fewer returns (which have been estimated at nearly a fifth of all online sales). And the closer AI companies get to the transaction, the more ways they have to make money from it.
And you know who really needs to figure out consumer monetization of AI right now? AI companies.

It’s October, which means two things: I have no idea where September went, and my bookkeeper would very much like to know where the money went.
That’s where Mercury Spend comes in. For each trip and video shoot, we set a budget and Mercury tracks the rest. It also makes receipts much less annoying. You can connect Gmail so Mercury automatically pulls them in, or batch-upload them yourself. Either way, it matches each receipt to the right expense automatically.
And because Spend lives right inside Mercury alongside our banking accounts and cards, I can see everything in one place instead of trying to reconstruct the month across a dozen different systems. That was especially useful last month, between shoots, editing and ping-ponging between the East and West Coasts.
Mercury is a fintech company, not an FDIC-insured bank. Banking services and debit cards provided through Choice Financial Group and Column N.A., Members FDIC. The IO Card is issued by Patriot Bank, N.A., Member FDIC, pursuant to a license from Mastercard International Incorporated.



Name: Ken Hamilton
What's your old thing? Bristle Buddy computer duster
What year is your old thing from? 2002
Why do you love your old thing? This was a giveaway item at a booth at an auto convention in Detroit. The company name has long since worn off the bottom—all that remains is that little red speck. I've used him to clean all the keyboards I've ever used for work and to sweep crumbs off my desk, but mostly he's there for moral support, smiling at me for the last 24 years.


Fun Fact: The word 'typewriter' can be typed entirely on the top row of a QWERTY keyboard. Originally, the R was placed somewhere else, but around 1874, engineers moved it to the top row so salespeople could type the word in one smooth demonstration for customers.
This newsletter was written and curated by Joanna Stern and Adele Lowitz.







