I don't wear loafers or any other type of dress shoes. My "dress shoes" are my boots. Now, I have a pair of high end wing tips to wear in the event I have to put on a suit, and that ain't gonna be too often. Other than that, I wear work boots to work and some variation of a sneaker to workout or cardio, and cowboy boots for everything else. I go to a very small country church where suits and sport coats make you look uppity, so it's usually jeans, occasionally khakis, and cowboy boots topped with a good felt fedora. Same for going out on the weekends with my lady. Boots and a thin ribbon fedora are a match made in heaven.
Last I looked I have about as many hats as pairs of boots. I mix and match as I see fit or more than likely what my beat-up feet are telling me to wear that particular day. Not all that stylish, but running shoes are always a safe bet no matter the hat size.
What I ride in is not generally what I wear working in the round pen. High heels, leather soles? Not the best use of a good boot in the sand. I rope but I don't do it for money. I also might get on the off side but I seldom get off on the off side. Almost never in a hurry to get on or off. Spurs, saddles, and the horse is a whole other game roping for time and $, measured in 100ths of a second. Heck of a lot easier to run ( or just walk) in a "roper" boot than it is in a buckaroo boot. And no one wants to trip over their spurs My work boots are pretty much all "roper" styled boots. Work here might be a trip to the irrigation store, feeding the various animals. An hour or so in the round pen with one of our young rank ones or moving pipe in a wet, early morning hay field. Very likely more "cowboys" have worn a fedora sized hat than have ever worn a big brimmed, movie style "cowboy" hat. Easier to keep a small hat on in the wind as well