It's really hard to figure out your style, fit, and the items that compliment it but a man that has done that work communicates a lot IMHO. It's a holistic picture.
If it's clear you've put thought into something whether it's your body, your written or spoken words, your "costume", your app design, or your code design; that communicates far more than just selecting for anyone not wearing something casual.
I used to use a similar process for finding employees: cast my net for Haskell / Scala / Erlang and I'll find the best programmers. While that bias held true to a degree it also excludes a large swath of people that might actually be a better fit, my failing there is not developing a multi-dimensional and rigorous process for finding and vetting.
Other forms of apparel are much more forgiving.
But even when I wasn't at my best, most suits are very forgiving in that area, it just needs to be tailored to your build (and not off the rack where they expect your shoulders, chest, hip be a certain generic proportion).
If we're just throwing free tailoring around, I'll also have my polo and khakis tailored, and then we can compare between them on the runway. It may well be that no style of clothing makes me look better than a suit, and that I still don't look good in one.
If you want to look good in a suit you can go get a $200 suit at any menswear store and if you want to look really good in a suit go spend $1500 for a tailored suit.
You can do either of these and get something acceptable without knowing anything about fashion.
If you want to look like a cultivated hipster, however, you have to work hard at it.