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My favorites are the 1903 Colt .32 and .380 hammerless. Nice gun to carry too. Of course there is always the Colt 1911, but it is a big gun to carry all day.

¡Que linda, felicitaciones!

Jakearoo:
I am both a collector and avid handgun user so I'll answer your question two ways.
Colts and Lugers are my primary collecting interest. I have,for example, several 38SPL Colt Officers Model Match revolvers that are collectible but can still be shot. These target pistols were hand assembled and hand tuned in the good old days of firearms manufacture here. I doubt if we'll ever see the likes of them made again as the expense would just be too high.
My working guns are a different matter. I usually carry a Beretta Model 96 in 40 S&W. This pistol is considered somewhat antiquated by many but it works well for me. In the warmer months I sometimes carry a S&W snubbie as it can be concealed even if you're in shorts and a tee shirt.
If I were to buy a new working handgun it would probably be one of the H&Ks or a Sig Sauer. I get to shoot just about every new pistol that comes on the market at the Scottsdale Gun Club and these two are my favorites.
I hope this helps and If I can answer any other questions I'd be glad to do so.
Jim

Jim,
As an accomplished handgunner, what are your thoughts on a P41 Remington? It's the only semi I have - a family heirloom no less but it seems like a pretty decent gun though light of caliber (.380). Can these take and occasional +P round?

Brent

Brent:
I think you mean a Remington Model 51 and I have a couple of them. The only other classic pocket pistol I favor over these is the Walther Model PP. This pistol was designed by a Remington Employee named Peterson who also designed the Peterson device which turned the Springfield 03 into a semiautomatic rifle.
The Model 51 is probably the best designed pocket pistol ever made in this Country and was a favorite police backup gun until more compact designs like the Seecamp came along. The biggest drawback to this pistol is it's a challange to disassemble.
I shoot mine occasionaly but would caution against using ammunition in any 70+ year old firearm for which it wasn't designed.
Jim

My Favorite carry gun is a Kimber Pro CDP in .45 ACP. With the aluminum frame it is a pleasure to carry in a Polymer Fobus holster, even though I have a nice Don Hume, I like the light weight of the fobus. They make a smaller model that is lighter, but I still prefer the slightly longer barrel length as well as a larger capacity magazine. There is nothing like the knock down power of a .45 ACP using Remington's Golden Saber ammo.

There's such an array of options for carry guns these days that I recommend anyone contemplating buying one go to a gun shop with a range. You can usually try out one or more of their rentals for free if they understand you're interested in buying. Run a few magazines through to see how comfortable you are handling the weapon. If it's possible draw and fire the pistol from the type of holster you'll be using for carry. Sit down with the gun on and make sure your comfortable. This is particularly important if you going to carry while driving.
If anyone reading this is new to pistol shooting I'd highly recommend you take at least one lesson in defensive pistol shoting from a trained instructor. What they teach you in most concealed carry classes isn't enough. Additionally; Regular practice is a must to maintain shoooting skills.

My 1903 .380 with silver tip is my carry. My 1911 is just too big for every day cary in my book. The 03 can squeeze 7+1 of hollow points. I think that could stop Cujo.

Colt 03s,and I own several, were probably the most popular carry pistol before concealed carry really became common. This pistol is another ingenious design and is still a viable weapon today even though the design is over 100 years old. The Colt 03 along with the Remington 51 cited above were probably the best of the American produced pocket pistols of the 20th Century and either could be an effective weapon today.
However,given a choice, I would opt for one of the newer designs as I wouldn't want to stake my life on a pistol that if human would be eligible to collect Social Security.
I'm going to try and take this thread back to the hobby we love and make a point here. I have no problem hunting with and shooting 100+ year old shotguns and that's the reason many post here. However I don't have to stake my life on the performance of these wonderful weapons of a bygone era and the criteria for a defensive handguns has to be and is quite different than it was in the last Century.
Jim

I would not put my life on the line with that old thing.
My std. arm is 1981 vintage CZ75. If I had to do it over again and got something American it would be Kahr MK40 or Kahr Micro 9.
PS. That thing is certainly weirdo looking, but true title of Pimp gun belongs to GOLDEN IMI Desert Eagle cal. .50.