My wife makes the "finest handmade wool vests on the planet. Period." as proclaimed by Sporting Classics magazine. I've got 4 or 5 myself, which is a good thing since I designed it, and designed it specifically for riding and cowboying. Granted they are spendy as they are handmade and out of expensive wool but they serve well. If you are wanting a vest that layers well, look at a wool vest. They just slip under a jacket or coat just right. A Trapper slipped into one of their pockets would still be there at the end of the day. I'd also suggest checking second hand stores. This is actually a deal in the cowboy world. I've actually got a "wino" (as we call something we get at a second hand store), jacket on right now I gave $3 for. I'll be wearing it all day out in the shop. You can often find very nice tweed items there for just a few bucks. Some of the wife's:
If you are more on the stand alone side the Carhart fleece line vests are pretty popular around here. Heck even the wife wears one:
However, the pockets are for keeping your hands warm, anything like a knife will fall out.
If you are wanting to try a vest and want to carry stuff in the pockets I'd sure recommend one of the newer softshell vests. Pretty darn practical. Zippered pockets to keep stuff put. Comfortable over a very wide array of temps and thin enough to slip under a jacket if needed. A lot of old farts like me still wear the wool:
But the young guys are all wearing the softshells.
I've got one myself and really like it. That's this cowboy's take on vests.