Is off-body carry an option? I know several public officials who have those day-planner style carrying "holsters." They are pretty discrete. I wouldn't rely on that alone, but along with ankle carry, it might work.
I know a guy who does this all the time. There have been more than a couple occasions when I have seen his gun laying around in a public place and babysat it for him until he came back.
I second the "sneaky pete" idea. I don't have one because business/formal clothing really isn't part of my routine, but it looks like a great way to hide a small pistol in plain sight.
I've never been able to actually hide/conceal a pistol in my pocket. The best that i think can be done for most of us is to camoflauge the pistol's profile and act like "yeah, so what? My pocket is full...of none of your business". And that only seems to work with pants like cargo pants or "dockers" that have pockets that are cut so you can actually draw without ending up like one of those trapped monkeys that can't get his fist-full of fruit out of the jar.
When i carry in a pocket, my pistol is in a holster in my pocket.
Some suggestions based on your body type:
pleated pants (even without a carry issue- they will look better with your frame)
consider a longer blazer (a longer body will help conceal a pocket carry- sleeves can shortened)
a tailor (a couple of bucks will get you looser thighs and deeper pockets- you might want to have a tailor build you something from scratch- or amend a pair of dockers).
Good luck.
Personally, I'd decide on my carry piece and build pants from that.
A competent tailor can make your "work" clothes work.
I'd rather have a $100 pair of khakis with a single stack 9mm or 45 -than a $50 pair of pants with any .380.
I do this everyday.
Kydex pocket holster and Duluth Trading Firehose pants. Deepest pockets I've found. I know this does nothing for you when wearing biz attire, but casual, good to go.
I carry a Sig 290RS or a Shield 9, not been seen.............yet. My employer will let me know when he does, with a pink slip.
I have a pocket holster with a thick piece of leather on the external face that makes my lcp look like a wallet in every pair of pants I own. So the holster leather is stitched to the thick leather piece. These holsters don't last forever as the leather softens over time ( years). They are cheap enough that replacement is acceptable. You might get one made with kydex that would last longer.
I pocket carry a Glock 43 with a Nemesis pocket holster in TruSpec 24-7 Cargo pants. TruSpec has large pockets and a large opening which makes pocket carry easy and weapon presentation pretty easy. Some pants have narrow pockets and narrow openings which makes getting to the gun a little difficult. I have tried 5.11 cargo pants but the front pocket opening does not make it easy to get to the gun.
Lcp or seecamp in a holster as described by Lonestar6 fits in my pocket and prints like a wallet. You can see the holster on Seecamp's site or at least it was shown there in the past.
LCP in cheapo (Galco?) holster. It is my go-to in dress attire generally. For some reason my waist on dress pants keeps shrinking, leaving my IWB options limited... I actually got married with my LCP on me a few years ago. I really don't see it as an option for any other pistol I own. I think a 642 or similar in the right pocket I might be able to pull off, but they way my pants fit typically nothing bigger. I'm 6'0", 240, 36w, with big legs. I use a PJ IWB holser, and I really like it. He sells a decent kydex pocket holster I always look at but never buy. Its nothing special, but would be slightly thinner than my current setup.
Would carrying in a breast pocket of a suit coat work in some cases? I really like the "custom pockets" idea as well.
my secret is to not pocket carry in the front pocket of jeans. Nearly impossible to retrieve. Jeans are not means to quick access to the front pockets.
When I do pocket carry, it's a Ruger LCP Custom in a Galco Pro 486 pocket holster. I've carried this one a lot over the summer in jeans and dress pants. I'm 5'9" 180. I've never been "outed" for carrying. As many have written above, most people are to self-absorbed to even notice. Good luck and stay safe.