I recall wearing my RM Williams on my first flying job in North America and they were not received well at all. Especially by females.
If you want to impress the Jilleroos and Jackaroos, then wear your R.M. Williams. If you had to suddenly walk for your survival, they might dramatically lessen your walking distance.
I'd suggest that Pilots take a look at the Costco Catalog and order on line some of the most fashionable work shoes that look professional and not like a cow boy.
Now, I can tell you that on one FAA ride I did, the inspector work Cowboy boots with spurs and a 10 gallon hat.
You could always go for the US Airforce flight boots on Ebay, and be right at home when you chug down a beer as you step out of the cockpit.