I tried using Google to redesign my wardrobe and the results were a disaster

In June 2023, Google launched a feature that allowed you to see how the same outfit would look on a variety of pre-selected models.

It was a useful tool, as chances were that at least one of the models would have roughly the same body shape as you.

Still, this rough approximation of trying on clothes couldn't compare to the real thing, so Google updated this feature in 2025 to allow you to become the model.

This feature, appropriately called Google Try-On, allows you to upload a photo of yourself and try on clothes digitally.

Just last week, Google updated Google Try-On to work within Circle to Search. The concept is simple. See an outfit, circle it, and try it on. What could be easier?

To test, I tried to build an outfit just using Circle to Search and Google Try-On.

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Can Circle to Search and Google Try-On really help me find the perfect outfit?

Theoretically, I could digitally try on an outfit within seconds of seeing it

The first step to using Google Try-On was to upload a picture of myself.

Google created a list of requirements that made the process feel akin to taking a passport photo, but eventually, I had taken the blandest possible photo of myself that I could. Armed with this photo, it was time to find some clothes.

I'm in the market for a new pair of blue jeans, so what better way to test Google Try-On than with the most common form of trouserwear.

First, I had to find a suitable person on social media. Scrolling through Instagram, I found a picture of a friend who not only had on a fairly neat pair of jeans, but some stylish brown boots to boot. Perfect.

Bizarrely, Google only recommended women's jeans to me, but I've always been told I'm shapely for a man, so I decided to give them a go. The result was ... fine.

I'm used to AI-generated photos, but this looked like a sloppy Photoshop job and wasn't the vibe check I was looking for. But what about something more adventurous?

What about, instead of replacing ripped jeans with undamaged ones, I asked Google to let me try on something new. With that in mind, I recalled a red jacket a friend had sent me a while back.

This was a little trickier as the jacket, featured in Ralph Lauren's Fall 2026 menswear presentation, is not currently on sale. But hey, it's fun to imagine, right? Unfortunately, the reality was deeply disappointing.

Not only did Google refuse to generate an image without the ripped jeans featured on the model, but it was apparently convinced that the look involved not wearing a shirt.

It took me a few tries to generate a picture of me with an undershirt on, and the result was as depressing as I'd expected.

No matter how many attempts it made, the results just didn't look right. If Google was aiming for this tool to be our go-to "vibe-check" for outfits, it completely missed the mark.

Even Circle to Search can't save Google Try-On

Google's search capabilities let it down again

I tried on clothes with Google Try-On a few more times, and not once did it impress me. Clothes appeared flat and shapeless on my body, and even trying out a few more poses in different lighting did little to change it.

Acknowledging Google's advice to avoid baggy clothing, I even tried the feature in just my underwear (You're welcome to this picture, Google), but nothing helped.

Strange results, like removing my shirt for no reason at all, were common, and even choosing the blandest clothes did little to help.

The other issue is that Google Try-On doesn't work with every picture Circle to Search finds.

In my initial search for jeans, I was only able to try on results from Amazon and SportsDirect. Neither site is one I like to go to for clothes, but they were the only websites Google Try-On let me use.

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It's unclear why some results aren't compatible with the feature. Google notes that sponsored results will not work with Try-On, but this didn't account for many of the results I saw.

Another problem is AI's inability to produce consistent results.

As I was wrapping up this article, I decided to give the red jacket another go. But this time, Google was unable to locate the original jacket despite the fact that I selected it with Circle to Search.

While this issue was the exception rather than the norm, it still led me to start the process from scratch multiple times.

Google Try-On is still just a curiosity

Google Try-On gave me a rough idea of what an outfit would look like on my body, but it didn't give me the confidence to buy an item.

None of the results it produced for me looked like I was actually wearing the clothes. I think Google aims too hard at realism here.

I tested an app called Glance AI last year, which produced AI-generated images of me wearing a variety of outfits. The results weren't realistic, but they gave a better idea of what an outfit looked like than Google Try-On.