The Amazon Echo Look had similar features:

https://www.theverge.com/2018/6/6/17431486/amazon-echo-look-...

I am not sure how well it did or if they are still selling it.

I have actually had this idea and have played with it in the past.

If I could guide you in a different direction:

Closet Management. I _would_ like tips on how to improve how I dress but I don't want my style to homogenized or labeled.

What I would want is essentially a local or cloud software that knows what I have in my closet, can manage what I have (is it dirty, is it clean, when did I last wear it, how worn out is it), can find new items that can integrate into my clothing, and will improve automation of this part of my life. So I can either present something to the visual AI and it judges it or I can have it optimize my clothes for the day for the weather and it will pick it out for me so I just have to put it on. Ideally, it would be a mode I toggle on where I don't even have to prompt; integrate it into my smart bed and it pops a notification of what to put on. The intention long-term would be having RFID tags in your clothes so the human doesn't have to manually maintain what's in the closet.

I think others have covered why catering this to 'fashionistas' likely won't work (it's their passion, they _want_ the effort). What you could likely cater to is people who want to look presentable and are somewhere between "vaguely knows what colors are" and "understands matching and style but wants to put it on cruise control".

The ground floor of the business is just the normal SaaS fee ($20+ / month easy). The upsell of the business is the maintenance of the closet ("your shirt looks worn out, can I buy a new one?" "Yes"... three days later, brand new shirt appears in their mailbox) along with either sponsored or partnered sales ("I think this belt would look nice with this outfit, it's $80, can I buy it?" "Yes")

If you search "Show HN" and wardrobe and fashion, I think you'll find a few other similar ideas from the past.

This probably isn't a group that really cares about fashion. Maybe if you lived in New York, but outside of that, most of the engineers I've met (US west coast) just wears random shorts and t shirts.

If you actually show up in something fancy, you'd stick out like an imposter or marketer or lawyer.

I definitely wouldn't pay money for this. But there's probably a strong regional and class component to this that I've just never been a part of.

IMHO those who care about style don’t need this, and those who couldn’t care less are happy without it.

I doubt there’s a third group that is interested in style but unable to match their socks to their polo shirts, and willing to go through all the work of signing up, taking pics of what they own, and then paying for your service to get advice…

This isn't a product that I'd personally use regardless of price, but it does sound like the sort of thing that might have a market for it.