A true connoisseur is not defined or recognized by his equipment and clothing. Those things maybe give you a hint, but what makes him a true connoisseur is his mentality and approach to the sport.
Obviously cycling circles around racing. You want to beat the other guy. That's why a true connoisseur has been racing for many years. Not necessarily a pro or former pro, but at least at the top amateur level. And he is still racing and has done it for +30 years probably since he was a kid. You can't be a connoisseur while in your 20s or 30s. It is earned over the years with lots of training and racing and riding your bike in all kinds of weather throughout the years.
The reason connoisseurs are racers is, that the whole sport evolves around racing. It's probably the most competetive sport there is. You race for the town sign, the top of the mountain, the next street light. You try to drop your buddies when pushing hard, you halfwheel if your buddies talk too much about Rapha, Pas Normal Maap, Baum or Speedvagen. It's all about winning. Even in these modern times, where most people log their training on Strava, you hunt KOMs. It's all about putting your name above the others'.
Since it's all about racing and winning, it's not about equipment and clothing. You don't pay much attention to your kit, because it's obvious what kit you're wearing. You're wearing your teamkit/cycling club kit, because you're proud wearing it, because you've won countless races wearing that kit. If it's wintertime and your team doesn't provide you with winter clothes, you certainly don't wear something that signals anything else than bikeriding. No fancy colors, no big logos, no fancy companies like Rapha e.g. Probably just some discrete black clothes like Assos.
Regarding the equipment, a true connoisseur knows, that it's not the bike that wins races, it's the hardness of the rider. We've all seen the dentist, and lawyers kind of riders and a connoisseur doesn't want to be confused with those guys. He rides a machine that has done a lot of racing and probably also some crashes hence severel battle scars, because that is part of racing. So the machine isn't perfect by WW standards. It's not even a WW bike. If he's riding Shimano, he will probably ride Ultegra because when riding +15k km a year, there has to be room/money for spares. He doesn't buy fancy parts like EE brakes, THM cranks and expensive wheels like Enve, Zipp or LW. And he doesn't care about stem length, saddle to bar drop and so on. He cares about riding in a bikeposition, that is comfortable and fast when spending countless hours on his machine, and that varies from rider to rider. But he certainly doesn't ride with +2 cm spacers under the stem, because he knows excactly what framesize fits him.
His bike is obviously always clean. His chain, chainrings, cogs and pulleywheels are clean, shiny and well lubricated before every ride because he respects his bike like the tool that will take him to victory. He doesn't leave anything to chance. The bike is silent, because he knows every part on his bike and knows if something is out of tune. And he knows how to fix most of it. Maybe he builds wheels himself, but he also knows, that there's no reason to do that, if he hasn't got the talent for it. In other words he knows his limitations and spends his time where it's well spent - like training rather than fixing the bike.
So the conclusion is, you probably wont recognize a true connoisseur on a café or bikeshop. But you recocnize him when he drops you in grouprides or passes you on a mountain. And he only talks about races he has won, where he did an inhuman effort or where some douchebag wheelsucker stole his win.