I have my G27 on right now. My wife, who knows I always carry, cannot tell I have it on without asking her to look for it sometimes. She always has my back and will tell me if I am grossly printing, she always gives me the once over before leaving anywhere. Practice makes perfect, and now she sometimes asks if I forgot to bring it!
Your holster and belt should be sorted out first. If you got that, you are good to go. I use a Milt Sparks VMII and double thick gun belt for my G27 and G29 (you'd like the belt being a machinist --it'll last you a lifetime). The holster does more than hold the gun and the belt more than hold up your pants. If you get a VMII for the G27, ask them to cut the holster so the pistol sets a little lower in the pants.
I say this because I am in a similar boat as you. I am 6' and weight about the same, I put on some weight after the army too so concealing something on the hip can be difficult. I can also hide both these pistols wearing pretty much anything I want. Also, I recently lost some weight, from 240 down to about 225 or so... It made concealment so much easier (not to mention I feel better).
I agree with the 5.11 pants as mentioned above, but that is just because I think they make comfortable useful pants. They come in cotton, but I like the nylon ones better. They are kind of like BDU's but more comfortable and less army looking. Although they do look tactical, and anyone else carrying will instantly recognize you as armed. I got the look the other day when I saw another fellow wearing the same pants as I... I could tell he could tell we both knew each other was carrying. They make shorts too, and cargo pants that aren't as tactical looking. Reasonably priced compared to Carhart (sp) and Levis. Not a big fan of the 5.11 shirts though. I like the Underarmor and the Tommy Bahama for summer, I wear fleece in the winter (so in the winter I can easily hide a G20 or whatever I want...)
On the other hand, with the rig I use, I can hide those two pistols just fine using denim shorts or cargo shorts, and an underarmor polo shirt. I print a little when I bend over, but not enough for me to worry about (it isn't a problem here). I'm not an undercover narc, so I don't need to dupe people into thinking I'm not armed. Conversely, I'd rather them have a little apprehension. Stay away. But I don't like to advertise either.
But the absolute best thing you can wear to hide a pistol is a Hawaiian print. I like the Tommy Bahama, they are a heavy silk and the patterns look nice, and I got a bunch when my wife worked there. Anyway, the pattern breaks up any printing. So if that is a problem, wear an underarmor t shirt tucked into the shorts, and then wear the print unbuttoned over that. Problem solved. Only issue is if you wear the pistol near the front of the hip, it will show when the wind blows. Again, this isn't an issue for me, but may be for you depending on your local laws. However, you won't be wearing this working on the lathe.
For your LCR, I have a S&W340PD. I just carry this thing in my pocket, no holster, but nothing else in the pocket either. It hides just fine, and sometimes I honestly forget it is there. Come to think of it, I actually went to the hardware store for some last minute items a few weeks ago... I was working around the house and still had my G27 on when I went. It wears pretty comfortable too, so much so that I was halfway into the store when I realized I was open carrying! Again, that isn't a problem for me, but still I'd like to have the awareness of it on my hip... I guess. It being that comfortable sure makes carry all day a breeze. I never leave without it.
Yeah, focus on the holster and the belt, get a couple of Hawaiian prints for when you are out, and with a little practice, you'll be able to hide the G27 in your Dickies. BTW, Milt Sparks sells tuckable clips for the VMII. I have them, got them back when they came free, but I never use them. They do work pretty well though.
If I were you, I'd consider the advice I've given on hiding in public using your regular clothes and a good rig with a proper, tight gun belt. For work, if absolute concealment is a must, then I'd say go with pocket revolver. It served me well in cases like that.
Hiding is an art. Most of us went through $1000 worth of holsters trying to find the right one to fit a $500 pistol just right. Some were lucky and did homework and found a better one sooner. Everyone will be different, but for me, the Milt Sparks has worked out so well with my body type and carry habits, that I have two identical holsters for both the 27 and 29, and I plan on getting another one very similar (they make an new one that rides lower, but basically the same thing) for a Glock 20 I plan on carrying in the winter and in the woods.
I remember thinking it was impossible awhile back though. Trying to use some of the Galco stuff and that Uncle Mikes junk. My best advice though has got to be to find a GREAT leather maker and get a double thick GUN belt (not a dept. store belt!).
Take care of that, adjust your clothing options some, and you'll be good to go. Oh yeah, getting your pants a size or two over is a good idea like the fellow said. All good advice on here.
Also, call up Milt Sparks. Mitch Rosen. Those guys should help you out, and they will give you good advice and not just try to sell you something (in fact, if you insist on something not in their ethos, they will send you elsewhere).
Good luck!
