Well hey Pete. Love this question. I myself have a long history with western dressing... which dates back to long before I even spent any time out west. I got my first pair of Justin boots at 12 and even a horse to go with them. Her name was Flying Paint.
Anyway. You're right – the RRL stuff is fantastic, and also easy to overdo. I have mentioned before that working at Polo felt like one long costume party. People had a lot of fun with their looks even if they weren't going any farther than the Fifth Avenue subway station. Ralph liked to script his collections as though they were movies, which makes sense, because the American West is such a cinematic-feeling place. You've got the mountains in the background, the prairie, the tumbleweeds, rivers wilder than anything we've got back East, a huge open sky. I sort of instantly see a guy on a horse with a rope in his hand. And I want to be that guy. Sounds like you do, too.
But you've been doing this for years, so you know – the goal is to not look like you're trying too hard to fit in among the real cowboys. With that in mind, I am going to give you a short packing list – jeans, sport shirts, belt, bandana, boots, jacket – with a few ideas around each one.
Denim is low-hanging fruit. I would only pack jeans, and don't over-complicate them. Just stick to indigo or stone or khaki, and make sure they're worn in a little. I'm all about presentation but you don't want to be the guy on the ranch with brand-new or pressed jeans. And have a bandana ready... we call it the back pocket square around here. They come in super handy – you can use it as an impromptu mask, to wipe some sweat from your brow, or to offer the lady next to you if she falls off her horse and needs some dusting off. Or even just to wipe the fingerprints off your phone screen. Back pocket squares don't cost much but are a godsend in a pinch – vacation or not. I'd pack a few... maybe both of these.
Where you really want to focus is on your shirts. Western shirts are fantastic (and clearly popular since we're nearly sold out of ours...re-up to come) – but I think almost any sport shirt tucked into your jeans and worn with a cowboy state of mind can feel right. Sport shirts are probably going to feel a little more natural and comfortable to you as a New Yorker, too. I love the faded-out plaids and chambrays – but even a graph check which is more East Coast, can look Western in that context. This chambray is my current favorite, but a blue-on-blue gingham would be pretty good, too. And I mentioned this earlier, but tucking it in is crucial for that old-school Western look – just look at Paul Newman in Hud, or Burt Lancaster in Vera Cruz or any of The Magnificent 7. I'm almost always gonna advocate for a tucked-in shirt, which is why ours are cut with a longer shirttail. Sometimes a guy who's new to us will say that his shirt is too long (by the way, we'll shorten it gratis) but it's for exactly this reason – so it'll stay tucked in.
...which means you can show off your belt! It's choose-your-own adventure here, although a wider belt strap tends to have that rancher vibe. We like a 1.25" strap – the oil leather is going to look more classic, but a zebra strap could give you kind of a cool Peter Beard-esque look. A safari's sort of an international cousin to a ranch, right? Either of these straps looks best with a bigger buckle. This oval plaque is fantastic, although if you get a chance to go into town, Wyoming is exactly the place to thrift some really killer vintage buckles. A longhorn, a ranch brand, whatever you can find. If it's got some scuffs and tarnish on it, all the better. This is something you can easily wear back home in NYC, too. Makes a cooler souvenir than a rabbit foot or a dreamcatcher. And lastly, not to state the obvious, but a hoof pick belt is a layup - just don't offer to use it next to the ranch hands.
And now – arguably the most essential part of your list – the boots. You may already have a pair, especially if you've been making this trip every summer, but if not, I'd suggest the roper. It's cowboy, but not as on the nose as a true western boot, with that higher heel and turned-up toe. The roper style is a little easier, with a shorter shaft, a lower heel, and a toe that just feels a touch less severe. It's the more understated boot, but just as functional. The vibe is more Townes Van Zandt at the kitchen table, less Ken Curtis in Gunsmoke. (Quick side story on that: I once bought a pair of incredible handmade cowboy boots on a trip to Italy from my favorite store in Milan, Eral55. Pretty sure I was working for Polo at the time. I think I was going for a spaghetti Western thing – Sergio Leone, maybe – but I couldn't resist these boots. But upon getting home to New York I realized very quickly they were just TOO MUCH COWBOY. I kinda knew it, but all Ann had to do was look at them... and then I really knew it. Serves me right for buying cowboy boots in Italy.) So, yeah, roper boots are pretty good for avoiding that, which I would recommend. They're not gonna look as costumey when you get back home.
Last thing I'd suggest... since I'm guessing you're flying, is a jacket. I say this a lot, but a blazer may get you a seat upgrade – and it acts as a purse. Our trailblazer jacket with the bellows pockets (you can put some feed for your horse in there) is perfect for this time of year in Wyoming. The fabric only gets cooler with age, once it's a little roughed-up. And it'll be great if you need to step things up for a family dinner in the lodge. A sport coat just makes you feel a little fresher, especially if you've been outside all day. Ann and I went on a friend's birthday trip to this ranch out in Santa Barbara, and I was working at Lands' End at the time. I had just finished this prototype for a safari jacket we were getting ready to put on the men's line. Like I said before – safari is not western, but I was excited enough to bring it. The ranch hands must have had a laugh about this because I ended up with a horse named Valentino. I'd wear it again, to be honest – but a sport jacket is probably your more functional outerwear option.
At the end of the day, the cowboy essence is more attitude than outfit. I know this isn't your first rodeo – or first trip out West, rather – but maybe it'll be the one where you feel the coolest? Safe travels and have fun. Come back with a cool belt buckle.