Thinking about the 141 ring shopping. Getting you the perfect ring..
Price would get something with diamond. That's non-negotiable in my opinion. If you want something else as the centerpiece, that's fine. Your gem of choice in the center, with smaller diamond accents maybe? Either way, I feel like Price would want to get something with diamond. Expect matching earrings if you wear them. I can see him getting something custom, and Laswell would help him. If you want something more feminine, he might struggle to get the vision. If you don't like what he got, he'll sulk for a day, but still buy you something else.
Simon, I think, would just ask what you want. He'd do it months before he proposes, and take you to ring stores to see what you like. Depending on how much you go jewelry shopping, you'd probably know he's thinking of proposing. If you like looking at jewelry a lot, it might not be obvious. He proposes very casually by the way, asks one day when you're both in the house. "Would you wanna get married?" In a tone that could almost be taken as hypothetical. If you say yes, you'd find a ring in your hand a second later; if you say no, he wouldn't say anything. He doesn't expect you to like what he gets, and despite his nonchalance he was internally freaking out when he asked.
Kyle actually would be the most romantic. John is very traditional in the "old fashioned" way, but Kyle is sort of the modern version of that. If you like masculine things, great! He's a masculine dude, he knows what's up. But it's not fragile masculinity, and he'd also be very comfortable getting familiar with feminine things. He'd learn about different cuts, talk in-depth to the people at the service counters, finding something perfect for you. I think overall, he'd have the most success in ring shopping alone and being creative about it- he can anticipate your taste. Talks to you about marriage before he proposes. He proposes in a way that aligns with your expectations.
You already have a ring from Johnny. He impulse bought you one early into the relationship. It's something between a promise ring, and his own special little gift. He knows he can be really unserious at times, or come off as a bit mindless. But once he realizes you might be the one, he gets you a ring. It's something vaguely you- your favorite gem stone in a simple cut, presented the second he gets it in a very unceremonious fashion (he doesn't want you to think it's an engagement ring). This also means that when he does buy your engagement ring, he'll be so ridiculously romantic and ceremonious about it. You can tell when he's planning on proposing, he's NOT subtle. He already knows your interests, and your ring will probably be like a more elegant version of the promise ring he got. You get proposed to in some stupidly scenic place- Johnny almost sticks out in it. The thought of rejection doesn't even cross his mind tbh.