During the winter I pretty much only wear western style throughout since I also have a claim to the lifestyle.
Here’s my (literally) top-down take on how to get started:
Cowboy Hats: Don’t wear one unless you’re in the lifestyle. The style and crease of your cowboy hat is a specific declaration of what kind of work you do. If you aren’t actually part of this group, don’t pretend because you’ll look like an idiot. You can wear a different type of hat if you wish, but make it your own.
Shirts: Plaid or plain button up work shirts. Jcrew makes some good modern workshirts and Frank & Oak has some good flannels. Tuck them in to your pants. You can wear a t-shirt underneath but it should never be a graphic tee.
Jackets: These really help complete the look. There’s a few I’d recommend. A denim, a tan, and a wool jacket. Denim can be shearling lined or not. I’d recommend the levi slim fit trucker. On that note, Levi did a collaboration with filson and made this awesome tin cloth trucker (make sure to click the tan option) I’d recommend filson for any of the western jackets. The tin cloth is really strong and breaks in sort of like raw denim creating a really cool patina. For the wool jacket I’d recommend their wool cruiser.
Pants: Denim or khaki depending on what else you’re wearing. the canadian tuxedo is pretty tough to pull off so throw those khakis in if you’re rolling the denim jacket. Don’t buy obvious designer denim (or anything) or you’ll look like a poser. functionality is the key to the style and obvious fashion gear ruins that.
Belts: Don’t wear a cowboy belt. They are another signifier of the lifestyle. If you aren’t in it, don’t pretend. Get a thick unadorned leather belt. I’ll be picking up one of these as soon as they get the tobacco color back in
Boots: I actually don’t wear cowboy boots very often. When I do I usually downplay the other western elements otherwise it comes across as too affected since I don’t live in Texas. I like to wear solid boots like redwing iron rangers. I think they complete the look without screaming that you’re trying to look like a cowboy.